(2R,3S,4aR,6S,7R,8aS)-6-[(2S,3R)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranylmethyl]-3-benzyloxy-2-(2-benzyloxy-ethyl)-2-methyl-7-triethylsilanyloxy-octahydro-pyrano[3,2-b]pyran

Base Information

Chemical Name:(2R,3S,4aR,6S,7R,8aS)-6-[(2S,3R)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranylmethyl]-3-benzyloxy-2-(2-benzyloxy-ethyl)-2-methyl-7-triethylsilanyloxy-octahydro-pyrano[3,2-b]pyran
CAS No.:537036-32-1
Molecular Formula:C₅₇H₇₄O₉SSi₂
Molecular Weight:991.446
Hs Code.:

(2R,3S,4aR,6S,7R,8aS)-6-[(2S,3R)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranylmethyl]-3-benzyloxy-2-(2-benzyloxy-ethyl)-2-methyl-7-triethylsilanyloxy-octahydro-pyrano[3,2-b]pyran

Synonyms:(2R,3S,4aR,6S,7R,8aS)-6-[(2S,3R)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranylmethyl]-3-benzyloxy-2-(2-benzyloxy-ethyl)-2-methyl-7-triethylsilanyloxy-octahydro-pyrano[3,2-b]pyran

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Chemical Property of (2R,3S,4aR,6S,7R,8aS)-6-[(2S,3R)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranylmethyl]-3-benzyloxy-2-(2-benzyloxy-ethyl)-2-methyl-7-triethylsilanyloxy-octahydro-pyrano[3,2-b]pyran

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Technology Process of (2R,3S,4aR,6S,7R,8aS)-6-[(2S,3R)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranylmethyl]-3-benzyloxy-2-(2-benzyloxy-ethyl)-2-methyl-7-triethylsilanyloxy-octahydro-pyrano[3,2-b]pyran

There total 11 articles about (2R,3S,4aR,6S,7R,8aS)-6-[(2S,3R)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranylmethyl]-3-benzyloxy-2-(2-benzyloxy-ethyl)-2-methyl-7-triethylsilanyloxy-octahydro-pyrano[3,2-b]pyran 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: 89.0%

: ((2R,3S)-3-Benzenesulfonyl-oxiranylmethoxy)-tert-butyl-diphenyl-silane

: 537036-31-0
Trifluoro-methanesulfonic acid (2S,3R,4aS,6R,7S,8aR)-7-benzyloxy-6-(2-benzyloxy-ethyl)-6-methyl-3-triethylsilanyloxy-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester

: 537036-32-1
(2R,3S,4aR,6S,7R,8aS)-6-[(2S,3R)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranylmethyl]-3-benzyloxy-2-(2-benzyloxy-ethyl)-2-methyl-7-triethylsilanyloxy-octahydro-pyrano[3,2-b]pyran

Guidance literature:: With n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -100 ℃;
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

: 537036-32-1
(2R,3S,4aR,6S,7R,8aS)-6-[(2S,3R)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranylmethyl]-3-benzyloxy-2-(2-benzyloxy-ethyl)-2-methyl-7-triethylsilanyloxy-octahydro-pyrano[3,2-b]pyran

Guidance literature:: Multi-step reaction with 7 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

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

: 537036-32-1
(2R,3S,4aR,6S,7R,8aS)-6-[(2S,3R)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranylmethyl]-3-benzyloxy-2-(2-benzyloxy-ethyl)-2-methyl-7-triethylsilanyloxy-octahydro-pyrano[3,2-b]pyran

Guidance literature:: Multi-step reaction with 10 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

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