(2S,4S,6S)-6-((R)-2-((tert-butyldiphenylsilyl)oxy)-4-(tert-butylthio)-4-oxobutyl)-2-((S)-2-hydroxy-4-((trimethylsilyl)methyl)pent-4-en-1-yl)-2-methoxy-3,3-dimethyltetrahydro-2H-pyran-4-yl acetate

Base Information

Chemical Name:(2S,4S,6S)-6-((R)-2-((tert-butyldiphenylsilyl)oxy)-4-(tert-butylthio)-4-oxobutyl)-2-((S)-2-hydroxy-4-((trimethylsilyl)methyl)pent-4-en-1-yl)-2-methoxy-3,3-dimethyltetrahydro-2H-pyran-4-yl acetate
CAS No.:1261423-11-3
Molecular Formula:C₄₃H₆₈O₇SSi₂
Molecular Weight:785.246
Hs Code.:

(2S,4S,6S)-6-((R)-2-((tert-butyldiphenylsilyl)oxy)-4-(tert-butylthio)-4-oxobutyl)-2-((S)-2-hydroxy-4-((trimethylsilyl)methyl)pent-4-en-1-yl)-2-methoxy-3,3-dimethyltetrahydro-2H-pyran-4-yl acetate

Synonyms:(2S,4S,6S)-6-((R)-2-((tert-butyldiphenylsilyl)oxy)-4-(tert-butylthio)-4-oxobutyl)-2-((S)-2-hydroxy-4-((trimethylsilyl)methyl)pent-4-en-1-yl)-2-methoxy-3,3-dimethyltetrahydro-2H-pyran-4-yl acetate

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Chemical Property of (2S,4S,6S)-6-((R)-2-((tert-butyldiphenylsilyl)oxy)-4-(tert-butylthio)-4-oxobutyl)-2-((S)-2-hydroxy-4-((trimethylsilyl)methyl)pent-4-en-1-yl)-2-methoxy-3,3-dimethyltetrahydro-2H-pyran-4-yl acetate

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Technology Process of (2S,4S,6S)-6-((R)-2-((tert-butyldiphenylsilyl)oxy)-4-(tert-butylthio)-4-oxobutyl)-2-((S)-2-hydroxy-4-((trimethylsilyl)methyl)pent-4-en-1-yl)-2-methoxy-3,3-dimethyltetrahydro-2H-pyran-4-yl acetate

There total 4 articles about (2S,4S,6S)-6-((R)-2-((tert-butyldiphenylsilyl)oxy)-4-(tert-butylthio)-4-oxobutyl)-2-((S)-2-hydroxy-4-((trimethylsilyl)methyl)pent-4-en-1-yl)-2-methoxy-3,3-dimethyltetrahydro-2H-pyran-4-yl acetate 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:

: 1261423-37-3
(2S,4S,6S)-6-((R)-2-((tert-butyldiphenylsilyl)oxy)-4-(tert-butylthio)-4-oxobutyl)-2-methoxy-3,3-dimethyl-2-(2-oxo-4-((trimethylsilyl)methyl)pent-4-en-1-yl)tetrahydro-2H-pyran-4-yl acetate

: (2S,4S,6S)-6-((R)-2-((tert-butyldiphenylsilyl)oxy)-4-(tert-butylthio)-4-oxobutyl)-2-((R)-2-hydroxy-4-((trimethylsilyl)methyl)pent-4-en-1-yl)-2-methoxy-3,3-dimethyltetrahydro-2H-pyran-4-ylacetate

: 1261423-11-3
(2S,4S,6S)-6-((R)-2-((tert-butyldiphenylsilyl)oxy)-4-(tert-butylthio)-4-oxobutyl)-2-((S)-2-hydroxy-4-((trimethylsilyl)methyl)pent-4-en-1-yl)-2-methoxy-3,3-dimethyltetrahydro-2H-pyran-4-yl acetate

Guidance literature:: (2S,4S,6S)-6-((R)-2-((tert-butyldiphenylsilyl)oxy)-4-(tert-butylthio)-4-oxobutyl)-2-methoxy-3,3-dimethyl-2-(2-oxo-4-((trimethylsilyl)methyl)pent-4-en-1-yl)tetrahydro-2H-pyran-4-yl acetate; With cerium(III) chloride heptahydrate; In methanol; at -42 - 20 ℃;

With sodium tetrahydroborate; In methanol; at -42 ℃; for 5h; optical yield given as %de;
DOI:10.1021/ja110198y

Reference yield:

: 1261423-35-1
(2S,4S,6S)-6-((R)-2-((tert-butyldiphenylsilyl)oxy)-4-(tert-butylthio)-4-oxobutyl)-2-(2-hydroxy-4-((trimethylsilyl)methyl)pent-4-en-1-yl)-2-methoxy-3,3-dimethyltetrahydro-2H-pyran-4-yl acetate

: (2S,4S,6S)-6-((R)-2-((tert-butyldiphenylsilyl)oxy)-4-(tert-butylthio)-4-oxobutyl)-2-((R)-2-hydroxy-4-((trimethylsilyl)methyl)pent-4-en-1-yl)-2-methoxy-3,3-dimethyltetrahydro-2H-pyran-4-ylacetate

: 1261423-11-3
(2S,4S,6S)-6-((R)-2-((tert-butyldiphenylsilyl)oxy)-4-(tert-butylthio)-4-oxobutyl)-2-((S)-2-hydroxy-4-((trimethylsilyl)methyl)pent-4-en-1-yl)-2-methoxy-3,3-dimethyltetrahydro-2H-pyran-4-yl acetate

Guidance literature:: Multi-step reaction with 2 steps

1.1: dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / -15 °C

1.2: 1 h / -15 °C

2.1: cerium(III) chloride heptahydrate / methanol / -42 - 20 °C

2.2: 5 h / -42 °C

With cerium(III) chloride heptahydrate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; 2.1: Luche reduction / 2.2: Luche reduction;
DOI:10.1021/ja110198y

Reference yield:

: 164662-96-8
1-trimethylsilyl-2-(tributylstannyl)methyl-2-propene

: (2S,4S,6S)-6-((R)-2-((tert-butyldiphenylsilyl)oxy)-4-(tert-butylthio)-4-oxobutyl)-2-((R)-2-hydroxy-4-((trimethylsilyl)methyl)pent-4-en-1-yl)-2-methoxy-3,3-dimethyltetrahydro-2H-pyran-4-ylacetate

: 1261423-11-3
(2S,4S,6S)-6-((R)-2-((tert-butyldiphenylsilyl)oxy)-4-(tert-butylthio)-4-oxobutyl)-2-((S)-2-hydroxy-4-((trimethylsilyl)methyl)pent-4-en-1-yl)-2-methoxy-3,3-dimethyltetrahydro-2H-pyran-4-yl acetate

Guidance literature:: Multi-step reaction with 3 steps

1.1: toluene / 12 h / Reflux

2.1: dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / -15 °C

2.2: 1 h / -15 °C

3.1: cerium(III) chloride heptahydrate / methanol / -42 - 20 °C

3.2: 5 h / -42 °C

With cerium(III) chloride heptahydrate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; toluene; 3.1: Luche reduction / 3.2: Luche reduction;
DOI:10.1021/ja110198y