trifluoromethanesulfonic acid (2S,3R,5S,6R)-5-benzyloxy-6-(2-benzyloxyethyl)-3-(tert-butyldimethylsilyloxy)-6-methyltetrahydropyran-2-ylmethyl ester

Base Information

• Chemical Name: trifluoromethanesulfonic acid (2S,3R,5S,6R)-5-benzyloxy-6-(2-benzyloxyethyl)-3-(tert-butyldimethylsilyloxy)-6-methyltetrahydropyran-2-ylmethyl ester
• CAS No.: 632354-32-6
• Molecular Formula: C₃₀H₄₃F₃O₇SSi
• Molecular Weight: 632.814

Synonyms:trifluoromethanesulfonic acid (2S,3R,5S,6R)-5-benzyloxy-6-(2-benzyloxyethyl)-3-(tert-butyldimethylsilyloxy)-6-methyltetrahydropyran-2-ylmethyl ester

Chemical Property of trifluoromethanesulfonic acid (2S,3R,5S,6R)-5-benzyloxy-6-(2-benzyloxyethyl)-3-(tert-butyldimethylsilyloxy)-6-methyltetrahydropyran-2-ylmethyl ester

Chemical Property:

Purity/Quality:

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Technology Process of trifluoromethanesulfonic acid (2S,3R,5S,6R)-5-benzyloxy-6-(2-benzyloxyethyl)-3-(tert-butyldimethylsilyloxy)-6-methyltetrahydropyran-2-ylmethyl ester

There total 8 articles about trifluoromethanesulfonic acid (2S,3R,5S,6R)-5-benzyloxy-6-(2-benzyloxyethyl)-3-(tert-butyldimethylsilyloxy)-6-methyltetrahydropyran-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:

benzyl bromide (100-39-0) → trifluoromethanesulfonic acid (2S,3R,5S,6R)-5-benzyloxy-6-(2-benzyloxyethyl)-3-(tert-butyldimethylsilyloxy)-6-methyltetrahydropyran-2-ylmethyl ester (632354-32-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / KHMDS / tetrahydrofuran; toluene / 0.5 h / 0 °C

2: 100 percent / TBAF / tetrahydrofuran / 18 h / 20 °C

3: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

4: 1.84 g / 2,6-lutidine / CH₂Cl₂ / 0.75 h

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

DOI:10.1021/jo035145d

Reference yield:

(2S,3R)-2-(2-benzyloxyethyl)-2-methyl-3-(toluene-4-sulfonyl)oxirane → trifluoromethanesulfonic acid (2S,3R,5S,6R)-5-benzyloxy-6-(2-benzyloxyethyl)-3-(tert-butyldimethylsilyloxy)-6-methyltetrahydropyran-2-ylmethyl ester (632354-32-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 81 percent / n-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran; hexane / 0.5 h / -100 °C

2: 93 percent / TsOH*H₂O / CH₂Cl₂ / 23 h / 0 °C

3: 99 percent / NaBH₄ / methanol; CH₂Cl₂ / 1 h / -78 °C

4: 100 percent / KHMDS / tetrahydrofuran; toluene / 0.5 h / 0 °C

5: 100 percent / TBAF / tetrahydrofuran / 18 h / 20 °C

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

7: 1.84 g / 2,6-lutidine / CH₂Cl₂ / 0.75 h

With 2,6-dimethylpyridine; sodium tetrahydroborate; n-butyllithium; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; toluene;

DOI:10.1021/jo035145d

Reference yield:

(4aS,6R,7S,8aR)-7-Benzyloxy-6-(2-benzyloxy-ethyl)-2,2-di-tert-butyl-6-methyl-hexahydro-1,3,5-trioxa-2-sila-naphthalene (537036-48-9) → trifluoromethanesulfonic acid (2S,3R,5S,6R)-5-benzyloxy-6-(2-benzyloxyethyl)-3-(tert-butyldimethylsilyloxy)-6-methyltetrahydropyran-2-ylmethyl ester (632354-32-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / TBAF / tetrahydrofuran / 18 h / 20 °C

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

3: 1.84 g / 2,6-lutidine / CH₂Cl₂ / 0.75 h

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

DOI:10.1021/jo035145d

upstream raw materials:

t-butyldimethylsiyl triflate

benzyl bromide

(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)-3-Benzyloxy-2-(2-benzyloxy-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-6-(3-trimethylsilanyl-prop-2-ynyl)-tetrahydro-pyran

(2S,3R,5S,6R)-5-benzyloxy-6-(2-benzyloxyethyl)-3-(tert-butyldimethylsilyloxy)-6-methyl-2-(prop-2-ynyl)tetrahydropyran

C₅₆H₈₈O₁₀Si₂

C₅₆H₈₈O₁₂Si₂

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