(2S,3R,5S,6R)-2-[(2S,3R)-2-benzenesulfonyl-3-(tert-butyldiphenylsilyloxymethyl)oxiranylmethyl]-5-benzyloxy-6-benzyloxymethyl-3-triethylsilyloxytetrahydropyran

Base Information

Chemical Name:(2S,3R,5S,6R)-2-[(2S,3R)-2-benzenesulfonyl-3-(tert-butyldiphenylsilyloxymethyl)oxiranylmethyl]-5-benzyloxy-6-benzyloxymethyl-3-triethylsilyloxytetrahydropyran
CAS No.:632354-42-8
Molecular Formula:C₅₂H₆₆O₈SSi₂
Molecular Weight:907.328
Hs Code.:

(2S,3R,5S,6R)-2-[(2S,3R)-2-benzenesulfonyl-3-(tert-butyldiphenylsilyloxymethyl)oxiranylmethyl]-5-benzyloxy-6-benzyloxymethyl-3-triethylsilyloxytetrahydropyran

Synonyms:(2S,3R,5S,6R)-2-[(2S,3R)-2-benzenesulfonyl-3-(tert-butyldiphenylsilyloxymethyl)oxiranylmethyl]-5-benzyloxy-6-benzyloxymethyl-3-triethylsilyloxytetrahydropyran

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Chemical Property of (2S,3R,5S,6R)-2-[(2S,3R)-2-benzenesulfonyl-3-(tert-butyldiphenylsilyloxymethyl)oxiranylmethyl]-5-benzyloxy-6-benzyloxymethyl-3-triethylsilyloxytetrahydropyran

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Technology Process of (2S,3R,5S,6R)-2-[(2S,3R)-2-benzenesulfonyl-3-(tert-butyldiphenylsilyloxymethyl)oxiranylmethyl]-5-benzyloxy-6-benzyloxymethyl-3-triethylsilyloxytetrahydropyran

There total 6 articles about (2S,3R,5S,6R)-2-[(2S,3R)-2-benzenesulfonyl-3-(tert-butyldiphenylsilyloxymethyl)oxiranylmethyl]-5-benzyloxy-6-benzyloxymethyl-3-triethylsilyloxytetrahydropyran 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: 89.0%

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

: 632354-41-7
Trifluoro-methanesulfonic acid (2S,3R,5S,6R)-5-benzyloxy-6-benzyloxymethyl-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl ester

: 632354-42-8
(2S,3R,5S,6R)-2-[(2S,3R)-2-benzenesulfonyl-3-(tert-butyldiphenylsilyloxymethyl)oxiranylmethyl]-5-benzyloxy-6-benzyloxymethyl-3-triethylsilyloxytetrahydropyran

Guidance literature:: With n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at -100 ℃; for 0.75h;
DOI:10.1021/jo035145d

Reference yield:

: 100-39-0
benzyl bromide

: 632354-42-8
(2S,3R,5S,6R)-2-[(2S,3R)-2-benzenesulfonyl-3-(tert-butyldiphenylsilyloxymethyl)oxiranylmethyl]-5-benzyloxy-6-benzyloxymethyl-3-triethylsilyloxytetrahydropyran

Guidance literature:: Multi-step reaction with 5 steps

1: 87 percent / KH / tetrahydrofuran / 1 h / 20 °C

2: 88 percent / TBAF / tetrahydrofuran / 17 h / 20 °C

3: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

4: 2.47 g / 2,6-lutidine / CH₂Cl₂ / 0.75 h

5: 89 percent / n-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 0.75 h / -100 °C

With 2,6-dimethylpyridine; n-butyllithium; tetrabutyl ammonium fluoride; potassium hydride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane;
DOI:10.1021/jo035145d

Reference yield:

: 632354-40-6
(2S,3R,5S,6R)-5-benzyloxy-6-benzyloxymethyl-2-hydroxymethyltetrahydropyran-3-ol

: 632354-42-8
(2S,3R,5S,6R)-2-[(2S,3R)-2-benzenesulfonyl-3-(tert-butyldiphenylsilyloxymethyl)oxiranylmethyl]-5-benzyloxy-6-benzyloxymethyl-3-triethylsilyloxytetrahydropyran

Guidance literature:: Multi-step reaction with 3 steps

1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

2: 2.47 g / 2,6-lutidine / CH₂Cl₂ / 0.75 h

3: 89 percent / n-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 0.75 h / -100 °C

With 2,6-dimethylpyridine; n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane;
DOI:10.1021/jo035145d