(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

Base Information

Chemical Name:(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
CAS No.:161984-61-8
Molecular Formula:C₃₁H₄₀O₆
Molecular Weight:508.655
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 8 articles about (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 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:

: 131311-17-6
[(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

: 161984-61-8
(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

Guidance literature:: Multi-step reaction with 7 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

4: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) CHCl₂, from -78 to 0 deg C

5: NaClO₂, NaH₂PO₄*H₂O, 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O; tetrahydrofuran / 1 h / 25 °C

6: 91 percent / TBAF / tetrahydrofuran / 8 h / 65 °C

7: 1.) 2,4,6-trichlorobenzoyl chloride, Et₃N, 2.) DMAP / 1.) THF, 0 deg C, 3 h, 2.) THF, benzene, 80 deg C, 2 h

With dmap; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; sodium carbonate; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; tert-butyl alcohol;
DOI:10.1021/ja00146a009

Reference yield:

: 161984-56-1
(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

: 161984-61-8
(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

Guidance literature:: Multi-step reaction with 6 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

3: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) CHCl₂, from -78 to 0 deg C

4: NaClO₂, NaH₂PO₄*H₂O, 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O; tetrahydrofuran / 1 h / 25 °C

5: 91 percent / TBAF / tetrahydrofuran / 8 h / 65 °C

6: 1.) 2,4,6-trichlorobenzoyl chloride, Et₃N, 2.) DMAP / 1.) THF, 0 deg C, 3 h, 2.) THF, benzene, 80 deg C, 2 h

With dmap; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium carbonate; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; tert-butyl alcohol;
DOI:10.1021/ja00146a009

Reference yield:

: 131311-18-7
(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

: 161984-61-8
(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

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) NaHMDS / 1.) THF, 0 deg C, 10 min, 2.) 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

4: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, 0.5 h

5: NaClO₂, NaH₂PO₄, 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 1 h / 25 °C

6: 91 percent / TBAF / tetrahydrofuran / 8 h / 65 °C

7: 1.) 2,4,6-trichlorobenzoyl chloride, Et₃N, 2.) DMAP / 1.) THF, 0 deg C, 2 h, 2.) THF, C₆H₆, 80 deg C, 1 h

With dmap; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; sodium carbonate; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; tert-butyl alcohol;
DOI:10.1021/ja00108a051