(2S,3R,4aS,6S,7R,8aS,9aR,10aR)-6-Benzyloxy-7-(2-benzyloxy-ethyl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-7-methyl-decahydro-1,8,10-trioxa-anthracen-3-ol

Base Information

Chemical Name:(2S,3R,4aS,6S,7R,8aS,9aR,10aR)-6-Benzyloxy-7-(2-benzyloxy-ethyl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-7-methyl-decahydro-1,8,10-trioxa-anthracen-3-ol
CAS No.:537036-52-5
Molecular Formula:C₄₅H₅₆O₇Si
Molecular Weight:737.021
Hs Code.:

(2S,3R,4aS,6S,7R,8aS,9aR,10aR)-6-Benzyloxy-7-(2-benzyloxy-ethyl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-7-methyl-decahydro-1,8,10-trioxa-anthracen-3-ol

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Chemical Property of (2S,3R,4aS,6S,7R,8aS,9aR,10aR)-6-Benzyloxy-7-(2-benzyloxy-ethyl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-7-methyl-decahydro-1,8,10-trioxa-anthracen-3-ol

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Technology Process of (2S,3R,4aS,6S,7R,8aS,9aR,10aR)-6-Benzyloxy-7-(2-benzyloxy-ethyl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-7-methyl-decahydro-1,8,10-trioxa-anthracen-3-ol

There total 13 articles about (2S,3R,4aS,6S,7R,8aS,9aR,10aR)-6-Benzyloxy-7-(2-benzyloxy-ethyl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-7-methyl-decahydro-1,8,10-trioxa-anthracen-3-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:

: 537036-33-2
(2S,4aS,6S,7R,8aS,9aR,10aR)-6-Benzyloxy-7-(2-benzyloxy-ethyl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-7-methyl-octahydro-1,8,10-trioxa-anthracen-3-one

: 537036-52-5
(2S,3R,4aS,6S,7R,8aS,9aR,10aR)-6-Benzyloxy-7-(2-benzyloxy-ethyl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-7-methyl-decahydro-1,8,10-trioxa-anthracen-3-ol

Guidance literature:: With sodium tetrahydroborate; In methanol; dichloromethane; at -78 ℃;
DOI:10.1016/S0040-4039(03)00252-1

Reference yield:

: 537036-26-3
(2S,3R,5S,6R)-5-benzyloxy-6-(2-benzyloxyethyl)-2-hydroxymethyl-6-methyltetrahydropyran-3-ol

: 537036-52-5
(2S,3R,4aS,6S,7R,8aS,9aR,10aR)-6-Benzyloxy-7-(2-benzyloxy-ethyl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-7-methyl-decahydro-1,8,10-trioxa-anthracen-3-ol

Guidance literature:: Multi-step reaction with 9 steps

1.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

1.2: 86 percent / CH₂Cl₂

2.1: 91 percent / n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -100 °C

3.1: 74 percent / TsOH / CHCl₃ / 55 °C

4.1: NaBH₄ / methanol; CH₂Cl₂ / -78 °C

5.1: TBAF / tetrahydrofuran / 20 °C

6.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

6.2: CH₂Cl₂

7.1: 89 percent / n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -100 °C

8.1: 74 percent / TsOH / CHCl₃ / 55 °C

9.1: NaBH₄ / methanol; CH₂Cl₂ / -78 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; n-butyllithium; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; chloroform;
DOI:10.1016/S0040-4039(03)00252-1

Reference yield:

: 537036-25-2
(4aS,6R,8aR)-6-(2-benzyloxyethyl)-2,2-di-tert-butyl-6-methyldecahydro-1,3,5-trioxa-2-silanaphthalen-7-one

: 537036-52-5
(2S,3R,4aS,6S,7R,8aS,9aR,10aR)-6-Benzyloxy-7-(2-benzyloxy-ethyl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-7-methyl-decahydro-1,8,10-trioxa-anthracen-3-ol

Guidance literature:: Multi-step reaction with 12 steps

1.1: NaBH₄ / methanol; CH₂Cl₂ / -78 °C

2.1: KH / tetrahydrofuran / 20 °C

3.1: TBAF / tetrahydrofuran / -78 °C

4.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

4.2: 86 percent / CH₂Cl₂

5.1: 91 percent / n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -100 °C

6.1: 74 percent / TsOH / CHCl₃ / 55 °C

7.1: NaBH₄ / methanol; CH₂Cl₂ / -78 °C

8.1: TBAF / tetrahydrofuran / 20 °C

9.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

9.2: CH₂Cl₂

10.1: 89 percent / n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / -100 °C

11.1: 74 percent / TsOH / CHCl₃ / 55 °C

12.1: NaBH₄ / methanol; CH₂Cl₂ / -78 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; n-butyllithium; tetrabutyl ammonium fluoride; potassium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; chloroform;
DOI:10.1016/S0040-4039(03)00252-1