[(2S,3R,4aS,6R,7S,9R,10aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,9-dimethyl-3-triisopropylsilanyloxy-decahydro-1,5-dioxa-benzocycloocten-6-yl]-acetonitrile

Base Information

Chemical Name:[(2S,3R,4aS,6R,7S,9R,10aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,9-dimethyl-3-triisopropylsilanyloxy-decahydro-1,5-dioxa-benzocycloocten-6-yl]-acetonitrile
CAS No.:596792-69-7
Molecular Formula:C₄₀H₆₃NO₅Si₂
Molecular Weight:694.115
Hs Code.:

[(2S,3R,4aS,6R,7S,9R,10aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,9-dimethyl-3-triisopropylsilanyloxy-decahydro-1,5-dioxa-benzocycloocten-6-yl]-acetonitrile

Synonyms:[(2S,3R,4aS,6R,7S,9R,10aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,9-dimethyl-3-triisopropylsilanyloxy-decahydro-1,5-dioxa-benzocycloocten-6-yl]-acetonitrile

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Chemical Property of [(2S,3R,4aS,6R,7S,9R,10aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,9-dimethyl-3-triisopropylsilanyloxy-decahydro-1,5-dioxa-benzocycloocten-6-yl]-acetonitrile

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Technology Process of [(2S,3R,4aS,6R,7S,9R,10aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,9-dimethyl-3-triisopropylsilanyloxy-decahydro-1,5-dioxa-benzocycloocten-6-yl]-acetonitrile

There total 9 articles about [(2S,3R,4aS,6R,7S,9R,10aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,9-dimethyl-3-triisopropylsilanyloxy-decahydro-1,5-dioxa-benzocycloocten-6-yl]-acetonitrile 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%

: 143-33-9,25596-52-5
sodium cyanide

: 596792-68-6
(2S,3R,4aS,6S,7S,9R,10aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-iodomethyl-2,9-dimethyl-3-triisopropylsilanyloxy-decahydro-1,5-dioxa-benzocycloocten-7-ol

: 596792-69-7
[(2S,3R,4aS,6R,7S,9R,10aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,9-dimethyl-3-triisopropylsilanyloxy-decahydro-1,5-dioxa-benzocycloocten-6-yl]-acetonitrile

Guidance literature:: In dimethyl sulfoxide; at 40 ℃; for 48h;
DOI:10.1021/jo049877x

Reference yield:

: 143-33-9,25596-52-5
sodium cyanide

: 596792-53-9
(2S,3R,4aS,6R,7S,9R,10aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-hydroxymethyl-2,9-dimethyl-3-triisopropylsilanyloxy-decahydro-1,5-dioxa-benzocycloocten-7-ol

: 596792-69-7
[(2S,3R,4aS,6R,7S,9R,10aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,9-dimethyl-3-triisopropylsilanyloxy-decahydro-1,5-dioxa-benzocycloocten-6-yl]-acetonitrile

Guidance literature:: (2S,3R,4aS,6R,7S,9R,10aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-hydroxymethyl-2,9-dimethyl-3-triisopropylsilanyloxy-decahydro-1,5-dioxa-benzocycloocten-7-ol; With 1H-imidazole; iodine; triphenylphosphine; 4 Angstroem MS; In tetrahydrofuran; at -30 - 0 ℃;

sodium cyanide; In dimethyl sulfoxide; at 40 ℃;
DOI:10.1016/S0040-4039(03)01214-0

Reference yield:

: 474125-28-5
(2R,4aR,6S,7R,9S,10aS)-6-Hydroxymethyl-2-(4-methoxy-phenyl)-9-methyl-octahydro-1,3,5-trioxa-benzocycloocten-7-ol

: 596792-69-7
[(2S,3R,4aS,6R,7S,9R,10aR)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-7-hydroxy-2,9-dimethyl-3-triisopropylsilanyloxy-decahydro-1,5-dioxa-benzocycloocten-6-yl]-acetonitrile

Guidance literature:: Multi-step reaction with 8 steps

1.1: 2,6-lutidine / CH₂Cl₂ / 0.42 h / -78 °C

1.2: CH₂Cl₂ / 0.5 h / -78 °C

2.1: n-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 0.67 h / -100 °C

3.1: 7.36 g / p-TsOH*H₂O; p-methoxybenzaldehyde dimethyl acetal / CHCl₃ / 2 h / 40 °C

4.1: 100 percent / NaBH₄ / CH₂Cl₂; methanol / 0.67 h / -78 °C

5.1: 100 percent / 2,6-lutidine / 1,2-dichloro-ethane / 3.33 h / 50 °C

6.1: 87 percent / aq. TFA / tetrahydrofuran / 25 h / 20 °C

7.1: 87 percent / imidazole; PPh₃; I₂ / tetrahydrofuran / 20 h / 0 °C

8.1: 97 percent / dimethylsulfoxide / 48 h / 40 °C

With 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; n-butyllithium; p-Anisaldehyde dimethyl acetal; iodine; toluene-4-sulfonic acid; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; chloroform; dimethyl sulfoxide; 1,2-dichloro-ethane;
DOI:10.1021/jo049877x