Toluene-4-sulfonic acid (2R,3S,4aR,6S,7R,8aS)-7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxy-7,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (2R,3S,4aR,6S,7R,8aS)-7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxy-7,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester
• CAS No.: 494760-63-3
• Molecular Formula: C₃₂H₅₈O₈SSi₂
• Molecular Weight: 659.045

Synonyms:Toluene-4-sulfonic acid (2R,3S,4aR,6S,7R,8aS)-7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxy-7,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester

Chemical Property of Toluene-4-sulfonic acid (2R,3S,4aR,6S,7R,8aS)-7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxy-7,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester

Chemical Property:

Purity/Quality:

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Technology Process of Toluene-4-sulfonic acid (2R,3S,4aR,6S,7R,8aS)-7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxy-7,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester

There total 5 articles about Toluene-4-sulfonic acid (2R,3S,4aR,6S,7R,8aS)-7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxy-7,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester 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: 84.0%

p-toluenesulfonyl chloride (98-59-9) + (2R,3S,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-hydroxymethyl-7,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-3-ol (494760-62-2) → Toluene-4-sulfonic acid (2R,3S,4aR,6S,7R,8aS)-7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxy-7,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester (494760-63-3)

Guidance literature:

With triethylamine; In dichloromethane; Heating;

DOI:10.1021/ja028726d

Reference yield:

((2R,4aR,6R,7S,8aR,9aS,10aS)-6-Hydroxy-6,10a-dimethyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-7-yl)-acetic acid ethyl ester (361534-79-4) → Toluene-4-sulfonic acid (2R,3S,4aR,6S,7R,8aS)-7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxy-7,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester (494760-63-3)

Guidance literature:

Multi-step reaction with 4 steps

1: LiAlH₄ / diethyl ether / 1 h / 0 °C

2: 1.56 g / 2,6-lutidine / CH₂Cl₂ / 2 h / Heating

3: 100 percent / H₂ / Pd(OH)2-C / ethyl acetate / 49 h

4: 599 mg / Et₃N / CH₂Cl₂ / 3 h / Heating

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; hydrogen; triethylamine; palladium hydroxide - carbon; In diethyl ether; dichloromethane; ethyl acetate;

DOI:10.1021/ja036984k

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → Toluene-4-sulfonic acid (2R,3S,4aR,6S,7R,8aS)-7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-hydroxy-7,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester (494760-63-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.56 g / 2,6-lutidine / CH₂Cl₂ / 2 h / Heating

2: 100 percent / H₂ / Pd(OH)2-C / ethyl acetate / 49 h

3: 599 mg / Et₃N / CH₂Cl₂ / 3 h / Heating

With 2,6-dimethylpyridine; hydrogen; triethylamine; palladium hydroxide - carbon; In dichloromethane; ethyl acetate;

DOI:10.1021/ja036984k

upstream raw materials:

p-toluenesulfonyl chloride

(2R,3S,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-hydroxymethyl-7,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-3-ol

t-butyldimethylsiyl triflate

((2R,4aR,6R,7S,8aR,9aS,10aS)-6-Hydroxy-6,10a-dimethyl-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracen-7-yl)-acetic acid ethyl ester

Downstream raw materials:

2-[(2R,4aR,5aS,6aR,8S,9R,10aS,11aR,13aS)-9-(tert-Butyl-dimethyl-silanyloxy)-9,10a-dimethyl-2-phenyl-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-8-yl]-ethanol

tert-Butyl-((2R,4aR,5aS,6aR,8S,9R,10aS,11aR,13aS)-9,10a-dimethyl-2-phenyl-8-vinyl-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalen-9-yloxy)-dimethyl-silane

C₆₂H₈₆O₁₃Si

9-[10-benzyloxy-8-(3-benzyloxy-propyl)-10a,11a-dimethyl-2-vinyl-tetradecahydro-1,5,7,11-tetraoxa-naphthacen-3-yloxy]-9,10a-dimethyl-2-phenyl-8-vinyl-dodecahydro-1,3,5,7,11-pentaoxa-benzo[4,5]cyclohepta[1,2-b]naphthalene

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