(3S,5S)-1-[(4S,5S,6R)-6-((2R,3S)-2-methyl-3-benzyloxy-buta-3-enyl)-2-phenyl-5-methyl-1,3-dioxan-4-yl]-3-tert-butyldimethylsilyl-5-methoxymethoxy-1-octyne

Base Information

Chemical Name:(3S,5S)-1-[(4S,5S,6R)-6-((2R,3S)-2-methyl-3-benzyloxy-buta-3-enyl)-2-phenyl-5-methyl-1,3-dioxan-4-yl]-3-tert-butyldimethylsilyl-5-methoxymethoxy-1-octyne
CAS No.:1258861-67-4
Molecular Formula:C₃₉H₅₈O₆Si
Molecular Weight:650.971
Hs Code.:

Synonyms:(3S,5S)-1-[(4S,5S,6R)-6-((2R,3S)-2-methyl-3-benzyloxy-buta-3-enyl)-2-phenyl-5-methyl-1,3-dioxan-4-yl]-3-tert-butyldimethylsilyl-5-methoxymethoxy-1-octyne

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Chemical Property of (3S,5S)-1-[(4S,5S,6R)-6-((2R,3S)-2-methyl-3-benzyloxy-buta-3-enyl)-2-phenyl-5-methyl-1,3-dioxan-4-yl]-3-tert-butyldimethylsilyl-5-methoxymethoxy-1-octyne

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Technology Process of (3S,5S)-1-[(4S,5S,6R)-6-((2R,3S)-2-methyl-3-benzyloxy-buta-3-enyl)-2-phenyl-5-methyl-1,3-dioxan-4-yl]-3-tert-butyldimethylsilyl-5-methoxymethoxy-1-octyne

There total 21 articles about (3S,5S)-1-[(4S,5S,6R)-6-((2R,3S)-2-methyl-3-benzyloxy-buta-3-enyl)-2-phenyl-5-methyl-1,3-dioxan-4-yl]-3-tert-butyldimethylsilyl-5-methoxymethoxy-1-octyne 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: 94.0%

: 1125-88-8
benzaldehyde dimethyl acetal

: 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

: 1258861-67-4
(3S,5S)-1-[(4S,5S,6R)-6-((2R,3S)-2-methyl-3-benzyloxy-buta-3-enyl)-2-phenyl-5-methyl-1,3-dioxan-4-yl]-3-tert-butyldimethylsilyl-5-methoxymethoxy-1-octyne

Guidance literature:: With 10-camphorsufonic acid; In dichloromethane; at 20 ℃;
DOI:10.1002/cjoc.201090280

Reference yield:

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

: 1258861-67-4
(3S,5S)-1-[(4S,5S,6R)-6-((2R,3S)-2-methyl-3-benzyloxy-buta-3-enyl)-2-phenyl-5-methyl-1,3-dioxan-4-yl]-3-tert-butyldimethylsilyl-5-methoxymethoxy-1-octyne

Guidance literature:: Multi-step reaction with 5 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

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

5.1: 10-camphorsufonic acid / dichloromethane / 20 °C

With n-butyllithium; Me₄NBH(OAc)3; 10-camphorsufonic acid; sodium hydrogencarbonate; Dess-Martin periodane; trifluoroacetic acid; In tetrahydrofuran; hexane; dichloromethane; water; acetic acid; acetonitrile;
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

: 1258861-67-4
(3S,5S)-1-[(4S,5S,6R)-6-((2R,3S)-2-methyl-3-benzyloxy-buta-3-enyl)-2-phenyl-5-methyl-1,3-dioxan-4-yl]-3-tert-butyldimethylsilyl-5-methoxymethoxy-1-octyne

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: 10-camphorsufonic acid / dichloromethane / 20 °C

With Me₄NBH(OAc)3; 10-camphorsufonic acid; trifluoroacetic acid; In dichloromethane; water; acetic acid; acetonitrile;
DOI:10.1002/cjoc.201090280