(4aS,6R,7S,9aR)-6-[(2R,3S)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranylmethyl]-octahydro-1,5-dioxa-benzocyclohepten-7-ol

Base Information

Chemical Name:(4aS,6R,7S,9aR)-6-[(2R,3S)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranylmethyl]-octahydro-1,5-dioxa-benzocyclohepten-7-ol
CAS No.:196795-34-3
Molecular Formula:C₃₅H₄₄O₇SSi
Molecular Weight:636.882
Hs Code.:

(4aS,6R,7S,9aR)-6-[(2R,3S)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranylmethyl]-octahydro-1,5-dioxa-benzocyclohepten-7-ol

Synonyms:(4aS,6R,7S,9aR)-6-[(2R,3S)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranylmethyl]-octahydro-1,5-dioxa-benzocyclohepten-7-ol

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Chemical Property of (4aS,6R,7S,9aR)-6-[(2R,3S)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranylmethyl]-octahydro-1,5-dioxa-benzocyclohepten-7-ol

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Technology Process of (4aS,6R,7S,9aR)-6-[(2R,3S)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranylmethyl]-octahydro-1,5-dioxa-benzocyclohepten-7-ol

There total 12 articles about (4aS,6R,7S,9aR)-6-[(2R,3S)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranylmethyl]-octahydro-1,5-dioxa-benzocyclohepten-7-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%

: 196795-22-9
(4aS,6R,7S,9aR)-6-[(2R,3S)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranylmethyl]-7-triethylsilanyloxy-octahydro-1,5-dioxa-benzocycloheptene

: 196795-34-3
(4aS,6R,7S,9aR)-6-[(2R,3S)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranylmethyl]-octahydro-1,5-dioxa-benzocyclohepten-7-ol

Guidance literature:: With toluene-4-sulfonic acid; In chloroform; at 0 ℃; for 2h;
DOI:10.1016/S0040-4020(97)00816-8

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 196795-34-3
(4aS,6R,7S,9aR)-6-[(2R,3S)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranylmethyl]-octahydro-1,5-dioxa-benzocyclohepten-7-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 85 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

2: 100 percent / n-BuLi, DMPU / tetrahydrofuran / 0.5 h / -100 °C

3: 97 percent / p-toluenesulfonic acid monohydrate / CHCl₃ / 2 h / 0 °C

With 1H-imidazole; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; toluene-4-sulfonic acid; In tetrahydrofuran; chloroform; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(97)00816-8

Reference yield:

: 181208-08-2
(2R,4aR,8aS)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-hexahydro-pyrano[3,2-b]pyran-3-one

: 196795-34-3
(4aS,6R,7S,9aR)-6-[(2R,3S)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranylmethyl]-octahydro-1,5-dioxa-benzocyclohepten-7-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) Me₃Al, 2.) pyridinium p-toluenesulfonate / 1.) CH₂Cl₂, -78 deg C, 1.5 h, 2.) MeOH, 25 deg C, 1 h.

2: 99 percent / tetra-n-butylammonium fluoride, AcOH / tetrahydrofuran / 4 h / 25 °C

3: 100 percent / Me₄NBH(OAc)3, AcOH / acetonitrile / 1 h / -20 °C

4: 1.) 2,6-lutidine / 1.) CH₃Cl₂, -78 deg C, 30 min, 2.) -78 deg C, 30 min.

5: 100 percent / n-BuLi, DMPU / tetrahydrofuran / 0.5 h / -100 °C

6: 97 percent / p-toluenesulfonic acid monohydrate / CHCl₃ / 2 h / 0 °C

With 2,6-dimethylpyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; tetrabutyl ammonium fluoride; trimethylaluminum; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; acetic acid; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; chloroform; acetonitrile;
DOI:10.1016/S0040-4020(97)00816-8