159734-07-3

Basic information

• Product Name: Borinic acid, dibutyl-, 1-[2-oxo-4-(phenylmethyl)-3-oxazolidinyl]-1-propenyl ester, (S)-
• CAS NO: 159734-07-3
• Molecular Formula: C21H32BNO3
• Molecular Weight: 357.301
• Mol File: 159734-07-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Borinic acid, dibutyl-, 1-[2-oxo-4-(phenylmethyl)-3-oxazolidinyl]-1-propenyl ester, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Borinic acid, dibutyl-, 1-[2-oxo-4-(phenylmethyl)-3-oxazolidinyl]-1-propenyl ester, (S)-(159734-07-3)
• EPA Substance Registry System: Borinic acid, dibutyl-, 1-[2-oxo-4-(phenylmethyl)-3-oxazolidinyl]-1-propenyl ester, (S)-(159734-07-3)

Safety Data

• Hazardous Substances Data: 159734-07-3(Hazardous Substances Data)

Upstream product

• 131685-53-5 (S)-4-benzyl-3-propionyl-2-oxazolidinone 
• 60669-69-4 di-n-butylboryl trifluoromethanesulfonate 

Downstream Products

• 393795-18-1 (S)-4-Benzyl-3-[(E)-(2S,3R)-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2-methyl-hex-4-enoyl]-oxazolidin-2-one 
• 113453-28-4 C₂₂H₂₃NO₄ 
• 131832-48-9 (4S)-4-benzyl-3-[(2S,3R)-3-hydroxy-2,4-dimethylpentanoyl]oxazolidin-2-one 
• 683226-19-9 (S)-4-Benzyl-3-[(2S,3R)-3-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-phenyl)-2-methyl-pentanoyl]-oxazolidin-2-one 
• 947696-79-9 (4S)-4-benzyl-3-[(2S,3R,4R,5S,8S)-3,5-bis(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-2,4,8-trimethylnonanoyl]-1,3-oxazolidin-2-one 
• 842125-05-7 (4S)-4-benzyl-3-[(2S,3R,4E)-3-hydroxy-6-(4-methoxybenzyloxy)-2-methylhex-4-enoyl]-1,3-oxazolidin-2-one 
• 947696-78-8 (4S)-4-benzyl-3-[(2S,3R,4S,5S,8S)-5-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-2,4,8-trimethylnonanoyl]-1,3-oxazolidin-2-one 
• 812649-71-1 (S)-4-benzyl-3-{(2S,3R,4S)-3-hydroxy-5-[(4-methoxybenzyl)oxy]-2,4-dimethylpentanoyl}oxazolidin-2-one 
• 159734-08-4 (S)-4-Benzyl-3-[(2S,3S)-6-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2-methyl-4-methylene-hexanoyl]-oxazolidin-2-one 

Relevant articles and documents

Sequencing cross-metathesis and non-metathesis reactions to rapidly access building blocks for synthesis

The olefin cross-metathesis reaction has been sequenced with four common organic transformations in a one- or two-pot manner to rapidly access useful building blocks. Those reactions are: (1) phosphorus-based olefination (e.g., Wittig and Horner-Wadsworth-Emmons); (2) hydride reduction; (3) Evans propionate aldol reaction; (4) Brown allyl- and Roush crotyl-boration. The products of these reactions include stereodefined 2,4-dienoates, trans allylic alcohols, syn-propionate aldols, and chiral non-racemic homoallylic alcohols, respectively. Many of these intermediates have been carried further to natural products, demonstrating the utility of the methodology.

The total synthesis and biological properties of the cytotoxic macrolide FD-891 and its non-natural (Z)-C12 isomer

A total, stereoselective synthesis of the naturally occurring, cytotoxic macrolide FD-891 and of its non-natural (Z)-C12 isomer is described. Three fragments of the main carbon chain were stereoselectively prepared by using asymmetric aldol and allylation reactions as the key steps. The molecule was then assembled by using two Julia-Kocienski olefinations to connect the three fragments and a Yamaguchi reaction to close the macrolactone ring. Some specific biological properties (cytotoxicity, binding to tubulin) have been determined for both macrolides. The E configuration of the C12-C13 olefinic bond seems to be an important feature in determining the cytotoxicity but the precise biological mechanism of the latter still remains to be cleared.

New Odorless Protocols for the Synthesis of Aldehydes and Ketones from Thiol Esters

Dodecanethiol esters derived from odorless dodecanethiol proved to be suitable substrates for Pd-catalyzed reduction with triethylsilane, coupling with organozinc reagents, and coupling with terminal acetylenes.