4-[(2R,3S,4aR,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,6,8a-trimethyl-octahydro-pyrano[3,2-b]pyran-2-yl]-butan-1-ol

Base Information

• Chemical Name: 4-[(2R,3S,4aR,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,6,8a-trimethyl-octahydro-pyrano[3,2-b]pyran-2-yl]-butan-1-ol
• CAS No.: 161984-58-3
• Molecular Formula: C₃₇H₅₈O₆Si
• Molecular Weight: 626.949

Synonyms:4-[(2R,3S,4aR,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,6,8a-trimethyl-octahydro-pyrano[3,2-b]pyran-2-yl]-butan-1-ol

Chemical Property of 4-[(2R,3S,4aR,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,6,8a-trimethyl-octahydro-pyrano[3,2-b]pyran-2-yl]-butan-1-ol

Chemical Property:

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Technology Process of 4-[(2R,3S,4aR,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,6,8a-trimethyl-octahydro-pyrano[3,2-b]pyran-2-yl]-butan-1-ol

There total 4 articles about 4-[(2R,3S,4aR,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,6,8a-trimethyl-octahydro-pyrano[3,2-b]pyran-2-yl]-butan-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: 97.0%

(2S,3R,4aS,6R,7S,8aR)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-7-(tert-butyl-dimethyl-silanyloxy)-6-[4-(tert-butyl-dimethyl-silanyloxy)-butyl]-2,4a,6-trimethyl-octahydro-pyrano[3,2-b]pyran (161984-57-2) → 4-[(2R,3S,4aR,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,6,8a-trimethyl-octahydro-pyrano[3,2-b]pyran-2-yl]-butan-1-ol (161984-58-3)

Guidance literature:

With camphor-10-sulfonic acid; In methanol; dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/ja00108a051 DOI:10.1021/ja00146a009

Reference yield:

[(2R,3S,4aR,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,6,8a-trimethyl-octahydro-pyrano[3,2-b]pyran-2-yl]-methanol (131311-17-6) → 4-[(2R,3S,4aR,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,6,8a-trimethyl-octahydro-pyrano[3,2-b]pyran-2-yl]-butan-1-ol (161984-58-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, -78 deg C, 10 min, 2.) THF, 0 deg C, 0.5 h

2: 100 percent / H₂, Na₂CO₃ / 10percent Pd/C / ethyl acetate / 12 h / 25 °C

3: 97 percent / CSA / CH₂Cl₂; methanol / 1 h / 0 °C

With camphor-10-sulfonic acid; hydrogen; sodium hexamethyldisilazane; sodium carbonate; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate;

DOI:10.1021/ja00146a009

Reference yield:

(2S,3R,4aS,6R,7S,8aR)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-7-(tert-butyl-dimethyl-silanyloxy)-6-[(Z)-4-(tert-butyl-dimethyl-silanyloxy)-but-1-enyl]-2,4a,6-trimethyl-octahydro-pyrano[3,2-b]pyran (161984-56-1) → 4-[(2R,3S,4aR,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,6,8a-trimethyl-octahydro-pyrano[3,2-b]pyran-2-yl]-butan-1-ol (161984-58-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / H₂, Na₂CO₃ / 10percent Pd/C / ethyl acetate / 12 h / 25 °C

2: 97 percent / CSA / CH₂Cl₂; methanol / 1 h / 0 °C

With camphor-10-sulfonic acid; hydrogen; sodium carbonate; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate;

DOI:10.1021/ja00108a051 DOI:10.1021/ja00146a009

upstream raw materials:

(2S,3R,4aS,6R,7S,8aR)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-7-(tert-butyl-dimethyl-silanyloxy)-6-[4-(tert-butyl-dimethyl-silanyloxy)-butyl]-2,4a,6-trimethyl-octahydro-pyrano[3,2-b]pyran

[(2R,3S,4aR,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,6,8a-trimethyl-octahydro-pyrano[3,2-b]pyran-2-yl]-methanol

(2S,3R,4aS,6R,7S,8aR)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-7-(tert-butyl-dimethyl-silanyloxy)-6-[(Z)-4-(tert-butyl-dimethyl-silanyloxy)-but-1-enyl]-2,4a,6-trimethyl-octahydro-pyrano[3,2-b]pyran

(2S,3S,4aR,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,6,8a-trimethyl-octahydro-pyrano[3,2-b]pyran-2-carbaldehyde

Downstream raw materials:

(2S,3R,4aS,5aR,10aS,11aR)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-2,4a,5a-trimethyl-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-one

4-[(2R,3S,4aR,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-hydroxy-2,6,8a-trimethyl-octahydro-pyrano[3,2-b]pyran-2-yl]-butyric acid

4-[(2R,3S,4aR,6S,7R,8aS)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-2,6,8a-trimethyl-octahydro-pyrano[3,2-b]pyran-2-yl]-butyric acid

Trifluoro-methanesulfonic acid (2S,3R,4aS,5aR,10aS,11aR)-3-benzyloxy-2-(2-benzyloxy-ethyl)-2,4a,5a-trimethyl-2,3,4,4a,5a,6,7,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-9-yl ester

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