263761-21-3

Basic information

• Product Name: (3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-pentanal
• Synonyms: (3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-pentanal
• CAS NO: 263761-21-3
• Molecular Weight: 352.546
• Mol File: 263761-21-3.mol

Chemical Properties

• CAS DataBase Reference: (3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-pentanal(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-pentanal(263761-21-3)
• EPA Substance Registry System: (3S,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-pentanal(263761-21-3)

Safety Data

• Hazardous Substances Data: 263761-21-3(Hazardous Substances Data)

Upstream product

• 214892-50-9 (4S,5S)-4-hydroxy-5-(4-methoxybenzyloxy)-1-hexene 
• 263761-20-2 tert-butyl(((2S,3S)-2-((4-methoxybenzyl)oxy)-hex-5-en-3-yl)oxy)dimethylsilane 

Downstream Products

• 263761-06-4 (E)-(7S,8S)-7-(tert-Butyl-dimethyl-silanyloxy)-8-(4-methoxy-benzyloxy)-4-methyl-non-4-enoic acid ethyl ester 
• 355387-00-7 (2R,6S)-2-{(4R,6S)-6-[(S)-1-(4-Methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-6-methyl-oct-7-en-2-ol 
• 355386-97-9 (S)-4-Isopropenyl-6-[(S)-1-(4-methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxane 
• 355386-98-0 1-{(4R,6S)-6-[(S)-1-(4-Methoxy-benzyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethanone 
• 355386-96-8 (5S,6S)-6-(4-Methoxy-benzyloxy)-2-methyl-hept-1-ene-3,5-diol 
• 152044-54-7 epothilone B 
• 263761-04-2 (5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-2-methyl-hept-1-en-3-ol 

Relevant articles and documents

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.

The 12,13-diol cyclization approach for a truly stereocontrolled total synthesis of epothilone B and the synthesis of a conformationally restrained analogue

A highly convergent and stereocontrolled synthesis of epothilone B (1) has been developed. The epoxide moiety in 1 was generated by regioselective mesylation and base treatment of the 12,13-diol 30 which was formed by a chelate Cram controlled Grignard addition of 14 and methyl ketone 13. Both fragments were synthesized from the chiral carbon pool precursors (S)-citronellol and (S)-lactic acid, respectively. A highly diastereoselective aldol additon of epoxy-aldehyde 7 and the known Southern hemisphere ketone 8 delivered the full carbon skeleton, containing all the stereogenic centers of 1. Functional group manipulation, macrolactonization and removal of two protecting groups then yielded 1. The spatial closeness of the C4-β-methyl and C6-methyl group in the crystal structure of 1 inspired us to connect them through a methylene bridge to give a cyclohexanone derivative. Thus, the Northern hemisphere aldehyde 7 was added to the enolate of the cyclohexanone 47. Further manipulations and macrolactonization delivered the conformationally restrained epothilone derivative 42.

How stable are epoxides? A novel synthesis of epothilone B

Remarkable stability of the oxirane function is displayed over a number of synthetic operations in a novel synthesis of the antitumor compound epothilone B. The cis-epoxide, generated very early by dihydroxylation of an (E)-olefin, was resistant to more than ten synthetic steps under a wide variety of reaction conditions. TBS = tert-butyldimethylsilyl.