(1R,2S,3S,4S)-4-(benzyloxy)-6-(tert-butyldiphenylsilyloxy)-1-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(triethylsilyloxy)-3-[(2-trimethylsilylethoxy)methoxy]hexan-1-ol

Base Information

Chemical Name:(1R,2S,3S,4S)-4-(benzyloxy)-6-(tert-butyldiphenylsilyloxy)-1-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(triethylsilyloxy)-3-[(2-trimethylsilylethoxy)methoxy]hexan-1-ol
CAS No.:1054673-08-3
Molecular Formula:C₄₆H₇₄O₈Si₃
Molecular Weight:839.345
Hs Code.:

(1R,2S,3S,4S)-4-(benzyloxy)-6-(tert-butyldiphenylsilyloxy)-1-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(triethylsilyloxy)-3-[(2-trimethylsilylethoxy)methoxy]hexan-1-ol

Synonyms:(1R,2S,3S,4S)-4-(benzyloxy)-6-(tert-butyldiphenylsilyloxy)-1-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(triethylsilyloxy)-3-[(2-trimethylsilylethoxy)methoxy]hexan-1-ol

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Chemical Property of (1R,2S,3S,4S)-4-(benzyloxy)-6-(tert-butyldiphenylsilyloxy)-1-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(triethylsilyloxy)-3-[(2-trimethylsilylethoxy)methoxy]hexan-1-ol

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Technology Process of (1R,2S,3S,4S)-4-(benzyloxy)-6-(tert-butyldiphenylsilyloxy)-1-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(triethylsilyloxy)-3-[(2-trimethylsilylethoxy)methoxy]hexan-1-ol

There total 7 articles about (1R,2S,3S,4S)-4-(benzyloxy)-6-(tert-butyldiphenylsilyloxy)-1-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(triethylsilyloxy)-3-[(2-trimethylsilylethoxy)methoxy]hexan-1-ol 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: 80.0%

: (2S,4R,5S,6S)-6-O-benzyl-8-O-(tert-butyldiphenylsilyl)-1,2-di-O-isopropylidene-4-O-(triethylsilyl)-5-O-(2-trimethylsilylethoxymethyl)-1,2,4,5,6,8-hexahydroxyoctan-3-one

: 1054673-08-3
(1R,2S,3S,4S)-4-(benzyloxy)-6-(tert-butyldiphenylsilyloxy)-1-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(triethylsilyloxy)-3-[(2-trimethylsilylethoxy)methoxy]hexan-1-ol

Guidance literature:: With lithium borohydride; In diethyl ether; at -90 ℃; for 2h;
DOI:10.1021/ol062570v

Reference yield:

: 914638-64-5
(S)-4-(tert-butyldiphenylsilyloxy)-2-benzyloxy-1-butanal

: 1054673-08-3
(1R,2S,3S,4S)-4-(benzyloxy)-6-(tert-butyldiphenylsilyloxy)-1-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(triethylsilyloxy)-3-[(2-trimethylsilylethoxy)methoxy]hexan-1-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: Chx₂BCl; triethylamine / diethyl ether / 1 h / 0 °C

1.2: diethyl ether / 5 h / 0 °C

1.3: 72 percent / phosphate buffer; H₂O₂ / diethyl ether; methanol; H₂O / 1 h / 20 °C / pH 7

2.1: 75 percent / 4-(dimethylamino)pyridine; i-Pr₂NEt / CH₂Cl₂ / 24 h / 20 °C

3.1: 80 percent / LiBH₄ / diethyl ether / 2 h / -90 °C

With dmap; lithium borohydride; dicyclohexylboron chloride; triethylamine; N-ethyl-N,N-diisopropylamine; In diethyl ether; dichloromethane; 1.2: aldol addition;
DOI:10.1021/ol062570v

Reference yield:

: 914638-70-3
(S)-4-(tert-butyldiphenylsilyloxy)-2-benzyloxy-1-butanol

: 1054673-08-3
(1R,2S,3S,4S)-4-(benzyloxy)-6-(tert-butyldiphenylsilyloxy)-1-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(triethylsilyloxy)-3-[(2-trimethylsilylethoxy)methoxy]hexan-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 0 °C

2.1: Chx₂BCl; triethylamine / diethyl ether / 1 h / 0 °C

2.2: diethyl ether / 5 h / 0 °C

2.3: 72 percent / phosphate buffer; H₂O₂ / diethyl ether; methanol; H₂O / 1 h / 20 °C / pH 7

3.1: 75 percent / 4-(dimethylamino)pyridine; i-Pr₂NEt / CH₂Cl₂ / 24 h / 20 °C

4.1: 80 percent / LiBH₄ / diethyl ether / 2 h / -90 °C

With dmap; lithium borohydride; oxalyl dichloride; dicyclohexylboron chloride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In diethyl ether; dichloromethane; 1.1: Swern oxidation / 2.2: aldol addition;
DOI:10.1021/ol062570v