Trifluoro-methanesulfonic acid (2S,3R,5S,6R)-5-benzyloxy-6-(2-benzyloxy-ethyl)-6-methyl-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Trifluoro-methanesulfonic acid (2S,3R,5S,6R)-5-benzyloxy-6-(2-benzyloxy-ethyl)-6-methyl-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 537036-27-4
• Molecular Formula: C₃₀H₄₃F₃O₇SSi
• Molecular Weight: 632.814

Synonyms:Trifluoro-methanesulfonic acid (2S,3R,5S,6R)-5-benzyloxy-6-(2-benzyloxy-ethyl)-6-methyl-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl ester

Chemical Property of Trifluoro-methanesulfonic acid (2S,3R,5S,6R)-5-benzyloxy-6-(2-benzyloxy-ethyl)-6-methyl-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of Trifluoro-methanesulfonic acid (2S,3R,5S,6R)-5-benzyloxy-6-(2-benzyloxy-ethyl)-6-methyl-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl ester

There total 5 articles about Trifluoro-methanesulfonic acid (2S,3R,5S,6R)-5-benzyloxy-6-(2-benzyloxy-ethyl)-6-methyl-3-triethylsilanyloxy-tetrahydro-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: 86.0%

trifluoromethylsulfonic anhydride (358-23-6) + triethylsilyl trifluoromethyl sulfonate (79271-56-0) + (2S,3R,5S,6R)-5-benzyloxy-6-(2-benzyloxyethyl)-2-hydroxymethyl-6-methyltetrahydropyran-3-ol (537036-26-3) → Trifluoro-methanesulfonic acid (2S,3R,5S,6R)-5-benzyloxy-6-(2-benzyloxy-ethyl)-6-methyl-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl ester (537036-27-4)

Guidance literature:

trifluoromethylsulfonic anhydride; (2S,3R,5S,6R)-5-benzyloxy-6-(2-benzyloxyethyl)-2-hydroxymethyl-6-methyltetrahydropyran-3-ol; With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃; for 0.5h;

triethylsilyl trifluoromethyl sulfonate; In dichloromethane;

DOI:10.1016/S0040-4039(03)00252-1

Reference yield:

(4aS,6R,8aR)-6-(2-benzyloxyethyl)-2,2-di-tert-butyl-6-methyldecahydro-1,3,5-trioxa-2-silanaphthalen-7-one (537036-25-2) → Trifluoro-methanesulfonic acid (2S,3R,5S,6R)-5-benzyloxy-6-(2-benzyloxy-ethyl)-6-methyl-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl ester (537036-27-4)

Guidance literature:

Multi-step reaction with 4 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

With 2,6-dimethylpyridine; sodium tetrahydroborate; tetrabutyl ammonium fluoride; potassium hydride; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/S0040-4039(03)00252-1

Reference yield:

(4aS,6R,7S,8aR)-6-(2-Benzyloxy-ethyl)-2,2-di-tert-butyl-6-methyl-hexahydro-1,3,5-trioxa-2-sila-naphthalen-7-ol (537036-47-8) → Trifluoro-methanesulfonic acid (2S,3R,5S,6R)-5-benzyloxy-6-(2-benzyloxy-ethyl)-6-methyl-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl ester (537036-27-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: KH / tetrahydrofuran / 20 °C

2.1: TBAF / tetrahydrofuran / -78 °C

3.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

3.2: 86 percent / CH₂Cl₂

With 2,6-dimethylpyridine; tetrabutyl ammonium fluoride; potassium hydride; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(03)00252-1

upstream raw materials:

trifluoromethylsulfonic anhydride

triethylsilyl trifluoromethyl sulfonate

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

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

Downstream raw materials:

(2R,3S,5R,6S)-6-[(2S,3R)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranylmethyl]-3-benzyloxy-2-(2-benzyloxy-ethyl)-2-methyl-5-triethylsilanyloxy-tetrahydro-pyran

(2S,3R,4aS,6R,7S,8aR)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-2-hydroxymethyl-6-methyl-octahydro-pyrano[3,2-b]pyran-3-ol

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

(2S,4aS,6R,7S,8aR)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-methyl-hexahydro-pyrano[3,2-b]pyran-3-one

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