(3S,4R,5R,6S,7S,10S,12S)-3-benzyloxy-10-(tert-butyldimethylsilyloxy)-12-methoxymethoxy-4,6-dimethylpentadec-1-en-8-yn-5,7-diol

Base Information

Chemical Name:(3S,4R,5R,6S,7S,10S,12S)-3-benzyloxy-10-(tert-butyldimethylsilyloxy)-12-methoxymethoxy-4,6-dimethylpentadec-1-en-8-yn-5,7-diol
CAS No.:1258861-80-1
Molecular Formula:C₃₂H₅₄O₆Si
Molecular Weight:562.863
Hs Code.:

Synonyms:(3S,4R,5R,6S,7S,10S,12S)-3-benzyloxy-10-(tert-butyldimethylsilyloxy)-12-methoxymethoxy-4,6-dimethylpentadec-1-en-8-yn-5,7-diol

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Chemical Property of (3S,4R,5R,6S,7S,10S,12S)-3-benzyloxy-10-(tert-butyldimethylsilyloxy)-12-methoxymethoxy-4,6-dimethylpentadec-1-en-8-yn-5,7-diol

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Technology Process of (3S,4R,5R,6S,7S,10S,12S)-3-benzyloxy-10-(tert-butyldimethylsilyloxy)-12-methoxymethoxy-4,6-dimethylpentadec-1-en-8-yn-5,7-diol

There total 20 articles about (3S,4R,5R,6S,7S,10S,12S)-3-benzyloxy-10-(tert-butyldimethylsilyloxy)-12-methoxymethoxy-4,6-dimethylpentadec-1-en-8-yn-5,7-diol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

: 1258861-79-8
(3S,4R,5R,6S,10S,12S)-3-benzyloxy-10-(tert-butyldimethylsilyloxy)-12-methoxymethoxy-4,6-dimethyl-5-hydroxy-pentadec-1-en-8-yn-7-one

: 1258861-80-1
(3S,4R,5R,6S,7S,10S,12S)-3-benzyloxy-10-(tert-butyldimethylsilyloxy)-12-methoxymethoxy-4,6-dimethylpentadec-1-en-8-yn-5,7-diol

Guidance literature:: With Me₄NBH(OAc)3; In acetic acid; acetonitrile; at -20 ℃; for 14h;
DOI:10.1002/cjoc.201090280

Reference yield:

: 1258861-78-7
(3S,4R,5R,6S,10S,12S)-3-benzyloxy-10-(tert-butyldimethylsilyloxy)-12-methoxymethoxy-4,6-dimethyl-5-trimethylsilyloxy-pentadec-1-en-8-yn-7-one

: 1258861-80-1
(3S,4R,5R,6S,7S,10S,12S)-3-benzyloxy-10-(tert-butyldimethylsilyloxy)-12-methoxymethoxy-4,6-dimethylpentadec-1-en-8-yn-5,7-diol

Guidance literature:: Multi-step reaction with 2 steps

1: trifluoroacetic acid / dichloromethane; water / 0.08 h / 20 °C

2: Me₄NBH(OAc)3 / acetic acid; acetonitrile / 14 h / -20 °C

With Me₄NBH(OAc)3; trifluoroacetic acid; In dichloromethane; water; acetic acid; acetonitrile;
DOI:10.1002/cjoc.201090280

Reference yield:

: 1-((4S)-2,2-dimethyl-1,3-dioxolan-4-yl)pentan-2-ol

: 1258861-80-1
(3S,4R,5R,6S,7S,10S,12S)-3-benzyloxy-10-(tert-butyldimethylsilyloxy)-12-methoxymethoxy-4,6-dimethylpentadec-1-en-8-yn-5,7-diol

Guidance literature:: Multi-step reaction with 13 steps

1.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 20 °C

2.1: lithium iodide / 0.17 h / -40 °C

2.2: -78 °C

3.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 20 °C

3.2: 0 - 20 °C

4.1: trifluoroacetic acid / dichloromethane; water / 20 °C

5.1: 2,6-dimethylpyridine / dichloromethane / -78 °C

6.1: 1H-imidazole; dmap / N,N-dimethyl-formamide / 20 °C

7.1: diisobutylaluminium hydride / dichloromethane; cyclohexane / -78 °C

8.1: Dess-Martin periodane

9.1: triphenylphosphine

10.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

10.2: 2 h / -78 °C

11.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.33 h / 20 °C

12.1: trifluoroacetic acid / dichloromethane; water / 0.08 h / 20 °C

13.1: Me₄NBH(OAc)3 / acetic acid; acetonitrile / 14 h / -20 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; n-butyllithium; Me₄NBH(OAc)3; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; lithium iodide; In tetrahydrofuran; hexane; dichloromethane; cyclohexane; water; acetic acid; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/cjoc.201090280