(2S,3R,4aS,5aR,8S,9R,10aS,11aR)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxymethyl)-4a,8-dimethyl-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-ol

Base Information

Chemical Name:(2S,3R,4aS,5aR,8S,9R,10aS,11aR)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxymethyl)-4a,8-dimethyl-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-ol
CAS No.:486394-86-9
Molecular Formula:C₃₇H₅₄O₇Si
Molecular Weight:638.917
Hs Code.:

(2S,3R,4aS,5aR,8S,9R,10aS,11aR)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxymethyl)-4a,8-dimethyl-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-ol

Synonyms:(2S,3R,4aS,5aR,8S,9R,10aS,11aR)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxymethyl)-4a,8-dimethyl-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-ol

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Chemical Property of (2S,3R,4aS,5aR,8S,9R,10aS,11aR)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxymethyl)-4a,8-dimethyl-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-ol

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Technology Process of (2S,3R,4aS,5aR,8S,9R,10aS,11aR)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxymethyl)-4a,8-dimethyl-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-ol

There total 7 articles about (2S,3R,4aS,5aR,8S,9R,10aS,11aR)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxymethyl)-4a,8-dimethyl-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-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: 96.0%

: 75-16-1
methylmagnesium bromide

: 486394-85-8
(2S,3R,4aS,5aR,9R,10aS,11aR)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxymethyl)-4a-methyl-2,3,4,4a,5a,10a,11,11a-octahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-one

: 486394-86-9
(2S,3R,4aS,5aR,8S,9R,10aS,11aR)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxymethyl)-4a,8-dimethyl-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-ol

Guidance literature:: In diethyl ether; toluene; at -78 ℃; for 0.583333h;
DOI:10.1021/ja028167a

Reference yield:

: (2S,3R,4aS,5aR,9R,10aS,11aR)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxymethyl)-4a-methyl-8-trimethylsilanyloxy-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalene

: 486394-86-9
(2S,3R,4aS,5aR,8S,9R,10aS,11aR)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxymethyl)-4a,8-dimethyl-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 41.8 mg / Pd(OAc)2 / acetonitrile / 0.83 h / 20 °C

2: 96 percent / toluene; diethyl ether / 0.58 h / -78 °C

With palladium diacetate; In diethyl ether; toluene; acetonitrile;
DOI:10.1021/ja028167a

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 486394-86-9
(2S,3R,4aS,5aR,8S,9R,10aS,11aR)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-9-(tert-butyl-dimethyl-silanyloxymethyl)-4a,8-dimethyl-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 94.3 mg / imidazole / dimethylformamide / 1.5 h / 0 °C

2: 92 percent / tetra-n-propylammonium perruthenate; N-methylmorpholine N-oxide; 4 Angstroem molecular sives / CH₂Cl₂ / 2 h / 20 °C

3: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

4: 41.8 mg / Pd(OAc)2 / acetonitrile / 0.83 h / 20 °C

5: 96 percent / toluene; diethyl ether / 0.58 h / -78 °C

With 1H-imidazole; palladium diacetate; tetrapropylammonium perruthennate; 4 Angstroem molecular sives; 4-methylmorpholine N-oxide; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/ja028167a