(2S,4aS,6R,7S,8aR)-7-benzyloxy-6-benzyloxymethyl-2-(tert-butyldiphenylsilyloxymethyl)octahydropyrano[3,2-b]pyran-3-one

Base Information

Chemical Name:(2S,4aS,6R,7S,8aR)-7-benzyloxy-6-benzyloxymethyl-2-(tert-butyldiphenylsilyloxymethyl)octahydropyrano[3,2-b]pyran-3-one
CAS No.:632354-43-9
Molecular Formula:C₄₀H₄₆O₆Si
Molecular Weight:650.887
Hs Code.:

Synonyms:(2S,4aS,6R,7S,8aR)-7-benzyloxy-6-benzyloxymethyl-2-(tert-butyldiphenylsilyloxymethyl)octahydropyrano[3,2-b]pyran-3-one

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Chemical Property of (2S,4aS,6R,7S,8aR)-7-benzyloxy-6-benzyloxymethyl-2-(tert-butyldiphenylsilyloxymethyl)octahydropyrano[3,2-b]pyran-3-one

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Technology Process of (2S,4aS,6R,7S,8aR)-7-benzyloxy-6-benzyloxymethyl-2-(tert-butyldiphenylsilyloxymethyl)octahydropyrano[3,2-b]pyran-3-one

There total 7 articles about (2S,4aS,6R,7S,8aR)-7-benzyloxy-6-benzyloxymethyl-2-(tert-butyldiphenylsilyloxymethyl)octahydropyrano[3,2-b]pyran-3-one 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: 82.0%

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

: 632354-43-9
(2S,4aS,6R,7S,8aR)-7-benzyloxy-6-benzyloxymethyl-2-(tert-butyldiphenylsilyloxymethyl)octahydropyrano[3,2-b]pyran-3-one

Guidance literature:: With toluene-4-sulfonic acid; In dichloromethane; at 55 ℃; for 4h;
DOI:10.1021/jo035145d

Reference yield:

: 100-39-0
benzyl bromide

: 632354-43-9
(2S,4aS,6R,7S,8aR)-7-benzyloxy-6-benzyloxymethyl-2-(tert-butyldiphenylsilyloxymethyl)octahydropyrano[3,2-b]pyran-3-one

Guidance literature:: Multi-step reaction with 6 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

6: 82 percent / TsOH*H₂O / CH₂Cl₂ / 4 h / 55 °C

With 2,6-dimethylpyridine; n-butyllithium; tetrabutyl ammonium fluoride; potassium hydride; toluene-4-sulfonic acid; 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

: 632354-43-9
(2S,4aS,6R,7S,8aR)-7-benzyloxy-6-benzyloxymethyl-2-(tert-butyldiphenylsilyloxymethyl)octahydropyrano[3,2-b]pyran-3-one

Guidance literature:: Multi-step reaction with 4 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

4: 82 percent / TsOH*H₂O / CH₂Cl₂ / 4 h / 55 °C

With 2,6-dimethylpyridine; n-butyllithium; toluene-4-sulfonic acid; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane;
DOI:10.1021/jo035145d