(S)-[(2R,3S)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranyl]-[(2R,3S,4aR,6R,8S,8aS)-8-benzyloxy-6-(3-benzyloxy-propyl)-2-methyl-3-triethylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-yl]-methanol

Base Information

Chemical Name:(S)-[(2R,3S)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranyl]-[(2R,3S,4aR,6R,8S,8aS)-8-benzyloxy-6-(3-benzyloxy-propyl)-2-methyl-3-triethylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-yl]-methanol
CAS No.:189348-02-5
Molecular Formula:C₅₈H₇₆O₁₀SSi₂
Molecular Weight:1021.47
Hs Code.:

(S)-[(2R,3S)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranyl]-[(2R,3S,4aR,6R,8S,8aS)-8-benzyloxy-6-(3-benzyloxy-propyl)-2-methyl-3-triethylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-yl]-methanol

Synonyms:(S)-[(2R,3S)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranyl]-[(2R,3S,4aR,6R,8S,8aS)-8-benzyloxy-6-(3-benzyloxy-propyl)-2-methyl-3-triethylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-yl]-methanol

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Chemical Property of (S)-[(2R,3S)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranyl]-[(2R,3S,4aR,6R,8S,8aS)-8-benzyloxy-6-(3-benzyloxy-propyl)-2-methyl-3-triethylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-yl]-methanol

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Technology Process of (S)-[(2R,3S)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranyl]-[(2R,3S,4aR,6R,8S,8aS)-8-benzyloxy-6-(3-benzyloxy-propyl)-2-methyl-3-triethylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-yl]-methanol

There total 19 articles about (S)-[(2R,3S)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranyl]-[(2R,3S,4aR,6R,8S,8aS)-8-benzyloxy-6-(3-benzyloxy-propyl)-2-methyl-3-triethylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-yl]-methanol 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: 63.0%

: 181207-92-1
((2S,3R)-3-Benzenesulfonyl-oxiranylmethoxy)-tert-butyl-diphenyl-silane

: 189348-01-4
(2S,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2-methyl-3-triethylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-carbaldehyde

: 189348-02-5
(S)-[(2R,3S)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranyl]-[(2R,3S,4aR,6R,8S,8aS)-8-benzyloxy-6-(3-benzyloxy-propyl)-2-methyl-3-triethylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-yl]-methanol

Guidance literature:: With n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -110 ℃;
DOI:10.1021/ja9701523

Reference yield: 25.0%

: 189348-01-4
(2S,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2-methyl-3-triethylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-carbaldehyde

: (+)-(Z)-(2R,3S)-3-(1'-tert-butyldiphenylsilyloxymethyl)-2-(p-tolylsulfonyl)oxirane

: 189348-02-5
(S)-[(2R,3S)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranyl]-[(2R,3S,4aR,6R,8S,8aS)-8-benzyloxy-6-(3-benzyloxy-propyl)-2-methyl-3-triethylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-yl]-methanol

: (R)-[(2R,3S)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranyl]-[(2R,3S,4aR,6R,8S,8aS)-8-benzyloxy-6-(3-benzyloxy-propyl)-2-methyl-3-triethylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-yl]-methanol

Guidance literature:: With n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; 1.) -100 deg C, 10 min, 2.) -80 deg C, 10 min;
DOI:10.1021/jo980320p

Reference yield:

: 189348-00-3
(2R,3S,4aR,6R,8S,8aS)-8-Benzyloxy-6-(3-benzyloxy-propyl)-2-hydroxymethyl-2-methyl-octahydro-pyrano[3,2-b]pyran-3-ol

: 189348-02-5
(S)-[(2R,3S)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranyl]-[(2R,3S,4aR,6R,8S,8aS)-8-benzyloxy-6-(3-benzyloxy-propyl)-2-methyl-3-triethylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-yl]-methanol

Guidance literature:: Multi-step reaction with 4 steps

1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

2: 92 percent / PPTS / CH₂Cl₂; methanol / 2 h / -20 °C

3: 96 percent / Et₃N, SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 3 h / Ambient temperature

4: 63 percent / n-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 1.) -100 deg C, 10 min, 2.) -80 deg C, 10 min

With 2,6-dimethylpyridine; n-butyllithium; pyridine-SO₃ complex; pyridinium p-toluenesulfonate; triethylamine; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; dimethyl sulfoxide;
DOI:10.1021/jo980320p