(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

Base Information

Chemical Name:(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
CAS No.:1258861-79-8
Molecular Formula:C₃₂H₅₂O₆Si
Molecular Weight:560.847
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 19 articles about (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 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: 98.0%

: 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

: 1258861-79-8
(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

Guidance literature:: With trifluoroacetic acid; In dichloromethane; water; at 20 ℃; for 0.0833333h;
DOI:10.1002/cjoc.201090280

Reference yield:

: 1199613-10-9
(3S,5S)-3-tert-butyldimethylsilyloxy-5-(methoxymethoxy)-1-octyne

: 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

Guidance literature:: Multi-step reaction with 3 steps

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

1.2: 2 h / -78 °C

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

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

With n-butyllithium; sodium hydrogencarbonate; Dess-Martin periodane; trifluoroacetic acid; In tetrahydrofuran; hexane; dichloromethane; water;
DOI:10.1002/cjoc.201090280

Reference yield:

: 1258861-68-5
C₂₁H₃₅NO₄Si

: 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

Guidance literature:: Multi-step reaction with 4 steps

1.1: diisobutylaluminium hydride / tetrahydrofuran; cyclohexane / -78 °C

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

2.2: 2 h / -78 °C

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

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

With n-butyllithium; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; trifluoroacetic acid; In tetrahydrofuran; hexane; dichloromethane; cyclohexane; water;
DOI:10.1002/cjoc.201090280