(2S,3R,4aS,5aR,8S,9R,10aS,11aR)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-9-(2,2-dibromo-vinyl)-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-(2,2-dibromo-vinyl)-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.:486394-88-1
Molecular Formula:C₃₂H₃₈Br₂O₆
Molecular Weight:678.458
Hs Code.:

(2S,3R,4aS,5aR,8S,9R,10aS,11aR)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-9-(2,2-dibromo-vinyl)-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-(2,2-dibromo-vinyl)-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-(2,2-dibromo-vinyl)-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-(2,2-dibromo-vinyl)-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 9 articles about (2S,3R,4aS,5aR,8S,9R,10aS,11aR)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-9-(2,2-dibromo-vinyl)-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:

: 558-13-4
carbon tetrabromide

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

: 486394-88-1
(2S,3R,4aS,5aR,8S,9R,10aS,11aR)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-9-(2,2-dibromo-vinyl)-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:: carbon tetrabromide; With triphenylphosphine; In dichloromethane; at 0 ℃; for 0.5h;

(2S,3R,4aS,5aR,8S,9S,10aS,11aR)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-8-hydroxy-4a,8-dimethyl-2,3,4,4a,5a,8,9,10a,11,11a-decahydro-1,5,10-trioxa-cyclohepta[b]naphthalene-9-carbaldehyde; With triethylamine; In dichloromethane; at 0 ℃; for 0.333333h; Further stages.;
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

: 486394-88-1
(2S,3R,4aS,5aR,8S,9R,10aS,11aR)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-9-(2,2-dibromo-vinyl)-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

1.1: 41.8 mg / Pd(OAc)2 / acetonitrile / 0.83 h / 20 °C

2.1: 96 percent / toluene; diethyl ether / 0.58 h / -78 °C

3.1: 87 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 20 °C

4.1: SO₃*pyridine; Et₃N / dimethylsulfoxide; CH₂Cl₂ / 1 h / 0 °C

5.1: PPh₃ / CH₂Cl₂ / 0.5 h / 0 °C

5.2: 17.3 mg / Et₃N / CH₂Cl₂ / 0.33 h / 0 °C

With palladium diacetate; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; triethylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; toluene; acetonitrile; 5.1: Corey-Fuchs reaction;
DOI:10.1021/ja028167a

Reference yield:

: (2S,3R,4aS,5aR,8S,9R,10aS,11aR)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-9-hydroxymethyl-4a-methyl-dodecahydro-1,5,10-trioxa-cyclohepta[b]naphthalen-8-ol

: 486394-88-1
(2S,3R,4aS,5aR,8S,9R,10aS,11aR)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-9-(2,2-dibromo-vinyl)-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 8 steps

1.1: 94.3 mg / imidazole / dimethylformamide / 1.5 h / 0 °C

2.1: 92 percent / tetra-n-propylammonium perruthenate; N-methylmorpholine N-oxide; 4 Angstroem molecular sives / CH₂Cl₂ / 2 h / 20 °C

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

4.1: 41.8 mg / Pd(OAc)2 / acetonitrile / 0.83 h / 20 °C

5.1: 96 percent / toluene; diethyl ether / 0.58 h / -78 °C

6.1: 87 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 20 °C

7.1: SO₃*pyridine; Et₃N / dimethylsulfoxide; CH₂Cl₂ / 1 h / 0 °C

8.1: PPh₃ / CH₂Cl₂ / 0.5 h / 0 °C

8.2: 17.3 mg / Et₃N / CH₂Cl₂ / 0.33 h / 0 °C

With 1H-imidazole; palladium diacetate; tetrapropylammonium perruthennate; pyridine-SO₃ complex; 4 Angstroem molecular sives; tetrabutyl ammonium fluoride; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; 8.1: Corey-Fuchs reaction;
DOI:10.1021/ja028167a