Category: 99438-28-5

Vuong, Sophie published the artcileFormal synthesis of TMC-69-6H via a one-pot enantioselective domino proline-mediated aldol/olefin homologation procedure, Application of (+)-B-Methoxydiisopinocampheylborane, the publication is Tetrahedron (2012), 68(2), 433-439, database is CAplus.

Enantioselective synthesis of TMC-69-6H (I) was accomplished from readily accessible pyridone derivative (II) via a domino proline-mediated aldol reaction/olefin homologation, followed by tandem ring-closing and cross metathesis.

Tetrahedron published new progress about 99438-28-5. 99438-28-5 belongs to ethers-buliding-blocks, auxiliary class Chiral,Aliphatic cyclic hydrocarbon, name is (+)-B-Methoxydiisopinocampheylborane, and the molecular formula is C18H34N4O5S, Application of (+)-B-Methoxydiisopinocampheylborane.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Nicolaou, K. C. published the artcileSynthesis of iso-epoxy-amphidinolide N and des-epoxy-caribenolide I structures. Revised strategy and final stages, Category: ethers-buliding-blocks, the publication is Organic & Biomolecular Chemistry (2006), 4(11), 2158-2183, database is CAplus and MEDLINE.

A general and highly convergent synthetic route to the macrocyclic core structures of the antitumor agents amphidinolide N and caribenolide I has been developed, and the total synthesis of iso-epoxy-amphidinolide N and des-epoxy-caribenolide I structures is described. Central to the revised strategy was the use of a Horner-Wadsworth-Emmons olefination between a β-ketophosphonate and an aldehyde to construct the C1-C13 sector common to both amphidinolide N and caribenolide I. Stereoselective alkylation allowed for the rapid assembly of the complete caribenolide I carbon skeleton. Key steps in the completion of the synthesis of des-epoxy-caribenolide I structure I included hydrolysis of a sensitive Me ester using Me₃SnOH, followed by regioselective macrolactonization of the resulting diol seco-acid and global deprotection. An analogous sequence of late-stage manoeuvres was used to arrive at the fully deprotected des-epoxy-amphidinolide N framework, obtained as a mixture of hemiacetal II and its bicyclic acetal. Regio- and diastereoselective epoxidation of the C6 methylene group in the bicyclic acetal provided access to iso-epoxy-amphidinolide N stereoisomer. Several of the prepared compounds were tested for cytotoxicity against human tumor cell lines, and none showed activity.

Organic & Biomolecular Chemistry published new progress about 99438-28-5. 99438-28-5 belongs to ethers-buliding-blocks, auxiliary class Chiral,Aliphatic cyclic hydrocarbon, name is (+)-B-Methoxydiisopinocampheylborane, and the molecular formula is C21H37BO, Category: ethers-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Brown, Herbert C. published the artcileEnantiomeric Z- and E-crotyldiisopinocampheylboranes. Synthesis in high optical purity of all four possible stereoisomers of β-methylhomoallyl alcohols, Recommanded Product: (+)-B-Methoxydiisopinocampheylborane, the publication is Journal of the American Chemical Society (1986), 108(2), 293-4, database is CAplus.

Enantiomerically pure Z-crotyldiisopinocampheylboranes are prepared from B-methoxydiisopinocampheylboranes and the allylic organopotassium compound from cis-2-butene. These enantiomeric Z-crotylboranes add to AcH regioselectively and stereoselectively to give erythro-(+)- and -(-)-3-methyl-4-penten-2-ols in ≥99% diastereoselectivities and ≥95% enantioselectivities. Similarly, enantiomeric E-crotyldiisopinocampheylboranes are prepared and add to AcH to give threo-(+)- and -(-)-3-methyl-4-penten-2-ols in ≥99% diastereoselectivities and ≥95% enantioselectivities.

Journal of the American Chemical Society published new progress about 99438-28-5. 99438-28-5 belongs to ethers-buliding-blocks, auxiliary class Chiral,Aliphatic cyclic hydrocarbon, name is (+)-B-Methoxydiisopinocampheylborane, and the molecular formula is C21H37BO, Recommanded Product: (+)-B-Methoxydiisopinocampheylborane.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Brown, Herbert C. published the artcileChiral synthesis via organoboranes. 7. Diastereoselective and enantioselective synthesis of erythro- and threo-β-methylhomoallyl alcohols via enantiomeric (Z)- and (E)-crotylboranes, Name: (+)-B-Methoxydiisopinocampheylborane, the publication is Journal of the American Chemical Society (1986), 108(19), 5919-23, database is CAplus and MEDLINE.

Isomerically pure (Z)- and (E)-crotylpotassiums were prepared by metalation of (Z)- and (E)-2-butene using a modified Schlosser procedure. The enantiomerically pure (Z)-crotyldiisopinocampheylboranes I and II were prepared by employing methoxydiisopinocampheylboranes, prepared from either (+)- or (-)-α-pinene, resp., and (Z)-crotylpotassium I and II retain their stereochem. identity under the reaction conditions and were condensed with RCHO (R = Me, Et, H₂C:CH, Ph) regioselectively and stereoselectively to yield the corresponding erythro-β-methylhomoallyl alcs. e.g., III, in ≥99% diastereoselectivities and ≥95% enantioselectivities. Similarly, the enantiomeric (E)-crotyldiisopinocampheylboranes were prepared and add to RCHO to yield the corresponding threo-β-methylhomoallyl alcs. with similar selectivities. Further, (Z)- and (E)-crotyldiisocaranylboranes IV were prepared and condensed with EtCHO to furnish the erythro– and threo-β-methylhomoallyl alcs., resp., in ≥99% diastereoselectivities and improved enantioselectivities (97%).

Journal of the American Chemical Society published new progress about 99438-28-5. 99438-28-5 belongs to ethers-buliding-blocks, auxiliary class Chiral,Aliphatic cyclic hydrocarbon, name is (+)-B-Methoxydiisopinocampheylborane, and the molecular formula is C21H37BO, Name: (+)-B-Methoxydiisopinocampheylborane.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Barrett, Anthony G. M. published the artcileApplications of Crotonyldiisopinocampheylboranes in Synthesis: Total Synthesis of Restrictinol, Name: (+)-B-Methoxydiisopinocampheylborane, the publication is Journal of Organic Chemistry (1999), 64(1), 162-171, database is CAplus and MEDLINE.

The total synthesis of restrictinol, the hydrolysis product of the antifungal natural product restricticin, starting from com. available Me (S)-(+)-3-hydroxy-2-methylpropionate was achieved. Key steps in the strategy involved (1) the use of Brown’s allylboration chem. to construct an acyclic intermediate bearing three of the four stereogenic centers of the natural product, (2) formation of a C-glycosidic vinyl iodide, and (3) introduction of the triene side chain via a Suzuki coupling reaction.

Journal of Organic Chemistry published new progress about 99438-28-5. 99438-28-5 belongs to ethers-buliding-blocks, auxiliary class Chiral,Aliphatic cyclic hydrocarbon, name is (+)-B-Methoxydiisopinocampheylborane, and the molecular formula is C21H37BO, Name: (+)-B-Methoxydiisopinocampheylborane.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Canova, Sophie published the artcileRearrangement of Homoallylic Alcohols Induced by DAST, Recommanded Product: (+)-B-Methoxydiisopinocampheylborane, the publication is Organic Letters (2006), 8(10), 2091-2094, database is CAplus and MEDLINE.

Nonracemic α-substituted-β-methoxy homoallylic alcs. RCH(OH)CH(OMe)CH:CH₂ [R = TBDPSOCH₂CH₂, PhCH₂OCH₂CH₂, (R)-TBDPSOCH₂CHMe, (S)-TBDPSOCH₂CHMeCH₂; TBDPS = Me₃CSi(Ph)₂; (I)] undergo diethylaminosulfur trifluoride (DAST)-mediated fluorination and rearrangement on silica gel to provide β,γ-unsaturated aldehydes RCH(CHO)CH:CH₂ [R = TBDPSOCH₂CH₂, PhCH₂OCH₂CH₂, (R)-TBDPSOCH₂CHMe, (S)-TBDPSOCH₂CHMeCH₂; (II)] in 76-90% yields and with good transfer of chirality. II are unstable to prolonged treatment with silica gel, rearranging to the corresponding α,β-unsaturated aldehydes, and are reduced with sodium borohydride to the primary homoallylic alcs. RCH(CH₂OH)CH:CH₂ [R = TBDPSOCH₂CH₂, PhCH₂OCH₂CH₂, (R)-TBDPSOCH₂CHMe, (S)-TBDPSOCH₂CHMeCH₂]. The racemic homoallylic alcs. PhCH₂CH(OH)CH₂CH:CH₂ and TBDPSOCH₂CH₂CH(OH)CH₂CH:CH₂ lacking an α-methoxy substituent undergo fluorination without rearrangement; reaction of the secondary alc. derived from I [R = (R)-TBDPSOCH₂CHMe] by hydrogenation of the olefin with DAST yields a complex mixture

Organic Letters published new progress about 99438-28-5. 99438-28-5 belongs to ethers-buliding-blocks, auxiliary class Chiral,Aliphatic cyclic hydrocarbon, name is (+)-B-Methoxydiisopinocampheylborane, and the molecular formula is C21H37BO, Recommanded Product: (+)-B-Methoxydiisopinocampheylborane.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Barrett, Anthony G. M. published the artcileAsymmetric Allylboration and Ring Closing Alkene Metathesis: A Novel Strategy for the Synthesis of Glycosphingolipids, SDS of cas: 99438-28-5, the publication is Journal of Organic Chemistry (2000), 65(20), 6508-6514, database is CAplus and MEDLINE.

A novel strategy for the synthesis of D,L-glucosylceramide (sic), a member of the glycosphingolipid class of natural products is described. Reagent-controlled asym. Brown allylboration gave excellent stereochem. control in the construction of adjacent stereocenters in the sphingoid base portion of the mol. The trans-configured double bond was obtained as a single geometrical isomer by use of silicon-tethered olefin metathesis employing the Schrock carbene [(CF₃)₂MeCO]₂Mo(:CHCMe₂Ph)(:NC₆H₃-2,6-i-Pr₂) and in situ PhLi-induced ring-opening of the intermediate 5,6-dihydro-2H-1,2-oxasiline followed by protodesilylation with TBAF in DMSO. The synthesis was completed by long chain amide formation and global deprotection.

Journal of Organic Chemistry published new progress about 99438-28-5. 99438-28-5 belongs to ethers-buliding-blocks, auxiliary class Chiral,Aliphatic cyclic hydrocarbon, name is (+)-B-Methoxydiisopinocampheylborane, and the molecular formula is C21H37BO, SDS of cas: 99438-28-5.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Zampella, Angela published the artcileStereochemistry of sphinxolides and reidispongiolides. Asymmetric synthesis of the C17-C22 fragment of reidispongiolide A, HPLC of Formula: 99438-28-5, the publication is European Journal of Organic Chemistry (2002), 785-790, database is CAplus.

Five fragments, [I (R = α, β-OH), II, III (R = α, β-OH)] embedding all the stereogenic centers of reidispongiolide A (IV), have been prepared by a controlled ozonolysis of the IV. The absolute stereochem. of the asym. centers of II, corresponding to the C17-C22 portion of IV, was determined by enantioselective synthesis and application of the advanced Mosher method.

European Journal of Organic Chemistry published new progress about 99438-28-5. 99438-28-5 belongs to ethers-buliding-blocks, auxiliary class Chiral,Aliphatic cyclic hydrocarbon, name is (+)-B-Methoxydiisopinocampheylborane, and the molecular formula is C4H7BrO2, HPLC of Formula: 99438-28-5.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Ahmed, Mahmood published the artcileA tripartite asymmetric allylboration – silicon tethered alkene ring closing metathesis – in situ ring opening protocol for the regiospecific generation of functionalized (E)-disubstituted homoallylic alcohols, Application of (+)-B-Methoxydiisopinocampheylborane, the publication is Tetrahedron (1999), 55(11), 3219-3232, database is CAplus.

Molybdenum carbene I catalyzed ring closing metathesis of (alkenyl)silyl ethers of homochiral allylic alcs., e.g. II, to afford 1,2-oxasilines, e.g. III, which were elaborated in situ to give (E)-4-alkyl-1,2- disubstituted 3-buten-1-ol and (Z)-4-alkyl-4-silyl-1,2-disubstituted 3-buten-1-ol derivatives as single geometric isomers.

Tetrahedron published new progress about 99438-28-5. 99438-28-5 belongs to ethers-buliding-blocks, auxiliary class Chiral,Aliphatic cyclic hydrocarbon, name is (+)-B-Methoxydiisopinocampheylborane, and the molecular formula is C21H37BO, Application of (+)-B-Methoxydiisopinocampheylborane.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Lemarchand, Aude published the artcileSynthesis of chiral ansa-bridged macrocyclic lactams ([16]metacyclophanes) related to geldanamycin, Computed Properties of 99438-28-5, the publication is Synthesis (2005), 1977-1990, database is CAplus.

Two chiral ansa-bridged lactams ([16]metacyclophanes) I (X = CH₂, O) were synthesized starting from 2-methoxyhydroquinone diisopropyl ether in 14 (I, X = CH₂, 3.9% overall) and 16 synthetic steps (I X = O, 0.6% overall). Both compounds contain typical features of geldanamycin in the C-1 to C-9 part of the ansa chain, i.e. the α,β,γ,δ-unsaturated anilide (C-1 to C-5), the carbamate at the stereogenic carbon atom C-7 and the E-double bond between C-8 and C-9. While the rest of the ansa chain (C-10 to C-15) was an alkyl chain in compound I (X = CH₂), a more polar CH₂OCH₂CH₂OCH₂ chain was installed in compound I (X = O). Key step of the sequence was a ring-closing metathesis in which the ansa compounds were formed as a mixture of isomers. Deprotection and oxidation to the quinone failed for diisopropyl ether I (X = O) but was successfully conducted with precursor I (X = CH₂).

Synthesis published new progress about 99438-28-5. 99438-28-5 belongs to ethers-buliding-blocks, auxiliary class Chiral,Aliphatic cyclic hydrocarbon, name is (+)-B-Methoxydiisopinocampheylborane, and the molecular formula is C21H37BO, Computed Properties of 99438-28-5.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem