Trifluoro-methanesulfonic acid (2R,3R,4S,5S,6S)-6-allyl-4-benzyloxy-5-hydroxy-5-methyl-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl ester

Base Information

Chemical Name:Trifluoro-methanesulfonic acid (2R,3R,4S,5S,6S)-6-allyl-4-benzyloxy-5-hydroxy-5-methyl-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl ester
CAS No.:870135-94-7
Molecular Formula:C₂₄H₃₇F₃O₇SSi
Molecular Weight:554.7
Hs Code.:

Trifluoro-methanesulfonic acid (2R,3R,4S,5S,6S)-6-allyl-4-benzyloxy-5-hydroxy-5-methyl-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl ester

Synonyms:Trifluoro-methanesulfonic acid (2R,3R,4S,5S,6S)-6-allyl-4-benzyloxy-5-hydroxy-5-methyl-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl ester

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Chemical Property of Trifluoro-methanesulfonic acid (2R,3R,4S,5S,6S)-6-allyl-4-benzyloxy-5-hydroxy-5-methyl-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl ester

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Technology Process of Trifluoro-methanesulfonic acid (2R,3R,4S,5S,6S)-6-allyl-4-benzyloxy-5-hydroxy-5-methyl-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl ester

There total 6 articles about Trifluoro-methanesulfonic acid (2R,3R,4S,5S,6S)-6-allyl-4-benzyloxy-5-hydroxy-5-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: 88.0%

: 870135-80-1
(2S,3S,4S,5R,6R)-2-Allyl-4-benzyloxy-6-hydroxymethyl-3-methyl-tetrahydro-pyran-3,5-diol

: 358-23-6
trifluoromethylsulfonic anhydride

: 79271-56-0
triethylsilyl trifluoromethyl sulfonate

: 870135-94-7
Trifluoro-methanesulfonic acid (2R,3R,4S,5S,6S)-6-allyl-4-benzyloxy-5-hydroxy-5-methyl-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: (2S,3S,4S,5R,6R)-2-Allyl-4-benzyloxy-6-hydroxymethyl-3-methyl-tetrahydro-pyran-3,5-diol; trifluoromethylsulfonic anhydride;

triethylsilyl trifluoromethyl sulfonate; With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃;
DOI:10.1002/anie.200501925

Reference yield:

: (1aS,2aR,6aR,7R,7aR)-7-Benzyloxy-5,5-di-tert-butyl-hexahydro-1,2,4,6-tetraoxa-5-sila-cyclopropa[b]naphthalene

: 870135-94-7
Trifluoro-methanesulfonic acid (2R,3R,4S,5S,6S)-6-allyl-4-benzyloxy-5-hydroxy-5-methyl-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: tetrahydrofuran / 0 °C

2.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

3.1: toluene / -78 °C

4.1: 98 percent / (HF)3*NEt₃ / tetrahydrofuran / 0 °C

5.2: 88 percent / 2,6-lutidine / CH₂Cl₂ / -78 °C

With oxalyl dichloride; dimethyl sulfoxide; triethylamine tris(hydrogen fluoride); triethylamine; In tetrahydrofuran; dichloromethane; toluene; 2.1: Swern oxidation;
DOI:10.1002/anie.200501925

Reference yield:

: (4aR,6S,8S,8aR)-6-Allyl-8-benzyloxy-2,2-di-tert-butyl-tetrahydro-1,3,5-trioxa-2-sila-naphthalen-7-one

: 870135-94-7
Trifluoro-methanesulfonic acid (2R,3R,4S,5S,6S)-6-allyl-4-benzyloxy-5-hydroxy-5-methyl-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: toluene / -78 °C

2.1: 98 percent / (HF)3*NEt₃ / tetrahydrofuran / 0 °C

3.2: 88 percent / 2,6-lutidine / CH₂Cl₂ / -78 °C

With triethylamine tris(hydrogen fluoride); In tetrahydrofuran; toluene;
DOI:10.1002/anie.200501925