263900-32-9

Basic information

• Product Name: (+)-METHYL (3S)-5-[(TERT-BUTYLDIMETHYLSILYL)OXY]-3-HYDROXY-2,2-DIMETHYLPENTANOATE
• Synonyms: (+)-METHYL (3S)-5-[(TERT-BUTYLDIMETHYLSILYL)OXY]-3-HYDROXY-2,2-DIMETHYLPENTANOATE;(3S)-5-[[(1,1-DiMethylethyl)diMethylsilyl]oxy]-3-hydroxy-2,2-diMethyl-pentanoic Acid Methyl Ester
• CAS NO: 263900-32-9
• Molecular Formula: C13H28O4Si
• Molecular Weight: 276.44
• Product Categories: Chiral Reagents
• Mol File: 263900-32-9.mol

Chemical Properties

• Appearance: /
• Solubility: Dichloromethane, Ether, Ethyl Acetate, Hexane
• CAS DataBase Reference: (+)-METHYL (3S)-5-[(TERT-BUTYLDIMETHYLSILYL)OXY]-3-HYDROXY-2,2-DIMETHYLPENTANOATE(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-METHYL (3S)-5-[(TERT-BUTYLDIMETHYLSILYL)OXY]-3-HYDROXY-2,2-DIMETHYLPENTANOATE(263900-32-9)
• EPA Substance Registry System: (+)-METHYL (3S)-5-[(TERT-BUTYLDIMETHYLSILYL)OXY]-3-HYDROXY-2,2-DIMETHYLPENTANOATE(263900-32-9)

Safety Data

• Hazardous Substances Data: 263900-32-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(+)-METHYL (3S)-5-[(TERT-BUTYLDIMETHYLSILYL)OXY]-3-HYDROXY-2,2-DIMETHYLPENTANOATE is used as a key intermediate in the synthesis of complex organic molecules. Its unique structure allows for the formation of various functional groups and the creation of a wide range of compounds with different applications in the chemical, pharmaceutical, and materials science industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (+)-METHYL (3S)-5-[(TERT-BUTYLDIMETHYLSILYL)OXY]-3-HYDROXY-2,2-DIMETHYLPENTANOATE is used as a building block for the development of new drugs. Its versatility in organic synthesis enables the creation of novel drug candidates with potential therapeutic properties, contributing to the advancement of medical treatments.
Used in Materials Science:
(+)-METHYL (3S)-5-[(TERT-BUTYLDIMETHYLSILYL)OXY]-3-HYDROXY-2,2-DIMETHYLPENTANOATE is also employed in materials science for the development of new materials with specific properties. Its incorporation into the molecular structure of these materials can lead to enhanced performance characteristics, such as improved mechanical strength, thermal stability, or chemical resistance.
Used in Chemical Industry:
In the chemical industry, (+)-METHYL (3S)-5-[(TERT-BUTYLDIMETHYLSILYL)OXY]-3-HYDROXY-2,2-DIMETHYLPENTANOATE serves as a versatile reagent for the production of various specialty chemicals. Its ability to participate in a range of chemical reactions makes it a valuable asset in the synthesis of compounds used in different applications, such as agrochemicals, dyes, and additives.

Upstream product

• 31469-15-5 1-methoxy-2-methyl-1-trimethylsiloxy-1-propene 
• 89922-82-7 3-(tert-butyldimethylsilanyloxy)propionaldehyde 
• 73842-99-6 3-tert-butyldimethylsilyloxy-1-propanol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 108794-10-1 4-[(tert-butyldimethylsilyl)oxy]-1-butene 

Downstream Products

• 218614-13-2 (-)-methyl (3S)-3,5-bis{[tert-butyl(dimethyl)silyl]oxy}-2,2-dimethylpentanoate 
• 308357-90-6 (-)-(3S,6R,7S,8S,12Z,15S,16E)-1,3,7-tris{[tert-butyl(dimethyl)silyl]oxy}-15-[(4-methoxybenzyl)oxy]-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)heptadeca-12,16-dien-5-one 
• 308357-88-2 (3S,6R,7S,8S,12Z,15S,16E)-1,3-bis{[tert-butyl(dimethyl)silyl]oxy}-7-hydroxy-15-[(4-methoxybenzyl)oxy]-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)heptadeca-12,16-dien-5-one 
• 308357-91-7 (3S,6R,7S,8S,12Z,15S,16E)-3,7-bis{[tert-butyl(dimethyl)silyl]oxy}-1-hydroxy-15-[(4-methoxybenzyl)oxy]-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)heptadeca-12,16-dien-5-one 
• 308357-92-8 (12Z,16E)-(3S,6R,7S,8S,15S)-3,7-Bis-(tert-butyl-dimethyl-silanyloxy)-15-(4-methoxy-benzyloxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-heptadeca-12,16-dienal 
• 308357-93-9 (3S,6R,7S,8S,12Z,15S,16E)-3,7-bis{[tert-butyl(dimethyl)silyl]oxy}-15-[(4-methoxybenzyl)oxy]-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid 
• 193146-26-8 (3S,6R,7S,8S,12Z,15S,16E)-3,7-bis{[tert-butyl(dimethyl)silyl]oxy}-15-hydroxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-1,3-thiazol-4-yl)-5-oxoheptadeca-12,16-dienoic acid 
• 193146-63-3 (12Z,16E)-(3S,6R,7S,8S,15S)-3,7,15-tris-(tert-butyl-dimethyl-silanyloxy)-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-heptadeca-12,16-dienoic acid 
• 193146-49-5 (7S,10R,11S,12S,19S,Z)-7-(tert-butyldimethylsilyloxy)-11-hydroxy-2,2,3,3,8,8,10,12,16,21,21,22,22-tridecamethyl-19-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)-4,20-dioxa-3,21-disilatricos-16-en-9-one 
• 193146-51-9 (7S,10R,11S,12S,19S,Z)-7,11-bis(tert-butyldimethylsilyloxy)-2,2,3,3,8,8,10,12,16,21,21,22,22-tridecamethyl-19-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)-4,20-dioxa-3,21-disilatricos-16-en-9-one 
• 193146-53-1 (5S,8R,9S,10S,17S,Z)-9-(tert-butyldimethylsilyloxy)-5-(2-hydroxyethyl)-2,2,3,3,6,6,8,10,14,19,19,20,20-tridecamethyl-17-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)-4,18-dioxa-3,19-disilahenicos-14-en-7-one 
• 189453-10-9 epothilone D 
• 189453-35-8 (4S,7R,8S,9S,13Z,16S,1'E)-4,8-di-tert-butyldimethylsilyloxy-5,5,7,9,13-pentamethyl-16-[1-methyl-2-(2-methyl-1,3-thiazol-4-yl)-1-ethenyl]-1-oxa-13-cyclohexadecene-2,6-dione 
• 152044-54-7 epothilone B 

Relevant articles and documents

Multi-step application of immobilized reagents and scavengers: A total synthesis of epothilone C

The total synthesis of the cytotoxic antitumour natural product epothilone C has provided a stage for the exploitation and further development of immobilized reagent methods. A stereoselective convergent synthetic strategy was applied, incorporating polymer-supported reagents, catalysts, scavengers and catch-and-release techniques to avoid frequent aqueous work-up and chromatographic purification.

A total synthesis of epothilones using solid-supported reagents and scavengers

A total synthesis of epothilone C(1) with concomitant formal synthesis of epothilone A is described, using immobilized reagents and scavengers to effect multistep synthetic transformations and purifications.

Method for producing epothilone B and derivatives, and intermediate products for this method

The invention relates to a method for producing epothilone B and derivatives, and to intermediate products for this method. According to the novel method, the epothilone B or derivatives are produced in high yields from the C1-C6, C7-C10 and C11-C20-fragm

Epothilone B and its derivatives as novel antitumor drugs: Total and partial synthesis and biological evaluation

Microtubule stabilizing natural products, as exemplified by paclitaxel (taxolR), are being considered as novel drugs against malignant therapy resistent solid tumors. Among these compounds, epothilone B and some of its derivatives have emerged as particularly promising candidates for industrial development. The total and partial syntheses of these compounds are described in detail, and some of the most important recent results on their biological activity are discussed.

Total Syntheses of Epothilones B and D

Total syntheses of the microtubule stabilizing antitumor drugs epothilone B and D are described, starting from optically pure (S)-malic acid and methyl (R)-3-hydroxy-2-methylpropionate. The synthesis is highly convergent by coupling the three fragments C1-C6 (fragment D), C7-C10 (fragment C), and C11-C21 (fragment B). Key steps are two stereoselective Wittig type olefinations to generate the 12,13- and 16,17-double bonds, an enantioselective Mukaiyama aldol addition to synthesize fragment D, and a sulfone anion allyl iodide alkylation to connect fragments B and C. Finally fragment D was attached to the B + C fragment via aldol addition.

Easy access to the epothilone family - Synthesis of epothilone B

An easy access to four out of five naturally occurring epothilones (A- E, 1-5) is reported. Key steps are an enantioselective Mukaiyama type aldol reaction, (E)- and (Z)-selective olefinations, and a sulfone alkylation.