(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

Base Information

Chemical Name:(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
CAS No.:596792-68-6
Molecular Formula:C₃₉H₆₃IO₅Si₂
Molecular Weight:795.002
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 7 articles about (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 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: 87.0%

: 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

: 596792-68-6
(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

Guidance literature:: With 1H-imidazole; iodine; triphenylphosphine; In tetrahydrofuran; at 0 ℃; for 20h;
DOI:10.1021/jo049877x

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

: 596792-68-6
(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

Guidance literature:: Multi-step reaction with 7 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

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; 1,2-dichloro-ethane;
DOI:10.1021/jo049877x

Reference yield:

: Trifluoro-methanesulfonic acid (2R,4aR,6S,7R,9R,10aS)-2-(4-methoxy-phenyl)-9-methyl-7-triethylsilanyloxy-octahydro-1,3,5-trioxa-benzocycloocten-6-ylmethyl ester

: 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

Guidance literature:: Multi-step reaction with 6 steps

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

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

3: 100 percent / NaBH₄ / CH₂Cl₂; methanol / 0.67 h / -78 °C

4: 100 percent / 2,6-lutidine / 1,2-dichloro-ethane / 3.33 h / 50 °C

5: 87 percent / aq. TFA / tetrahydrofuran / 25 h / 20 °C

6: 87 percent / imidazole; PPh₃; I₂ / tetrahydrofuran / 20 h / 0 °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; 1,2-dichloro-ethane;
DOI:10.1021/jo049877x