(2S,3S,4S,5R,6R)-2,6-Diallyl-4-benzyloxy-3-methyl-tetrahydro-pyran-3,5-diol

Base Information

Chemical Name:(2S,3S,4S,5R,6R)-2,6-Diallyl-4-benzyloxy-3-methyl-tetrahydro-pyran-3,5-diol
CAS No.:870135-81-2
Molecular Formula:C₁₉H₂₆O₄
Molecular Weight:318.413
Hs Code.:

Synonyms:(2S,3S,4S,5R,6R)-2,6-Diallyl-4-benzyloxy-3-methyl-tetrahydro-pyran-3,5-diol

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Chemical Property of (2S,3S,4S,5R,6R)-2,6-Diallyl-4-benzyloxy-3-methyl-tetrahydro-pyran-3,5-diol

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Technology Process of (2S,3S,4S,5R,6R)-2,6-Diallyl-4-benzyloxy-3-methyl-tetrahydro-pyran-3,5-diol

There total 9 articles about (2S,3S,4S,5R,6R)-2,6-Diallyl-4-benzyloxy-3-methyl-tetrahydro-pyran-3,5-diol 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: 78.0%

: 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

: 7486-35-3
tri-n-butyl(vinyl)tin

: 870135-81-2
(2S,3S,4S,5R,6R)-2,6-Diallyl-4-benzyloxy-3-methyl-tetrahydro-pyran-3,5-diol

Guidance literature:: Trifluoro-methanesulfonic acid (2R,3R,4S,5S,6S)-6-allyl-4-benzyloxy-5-hydroxy-5-methyl-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl ester; tri-n-butyl(vinyl)tin; With n-butyllithium; In tetrahydrofuran; at -78 ℃;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃;
DOI:10.1002/anie.200501925

Reference yield:

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

: 870135-81-2
(2S,3S,4S,5R,6R)-2,6-Diallyl-4-benzyloxy-3-methyl-tetrahydro-pyran-3,5-diol

Guidance literature:: Multi-step reaction with 2 steps

1.2: 88 percent / 2,6-lutidine / CH₂Cl₂ / -78 °C

2.1: n-BuLi; CuCN / tetrahydrofuran / -78 °C

2.2: 78 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0 °C

With n-butyllithium; In tetrahydrofuran;
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

: 870135-81-2
(2S,3S,4S,5R,6R)-2,6-Diallyl-4-benzyloxy-3-methyl-tetrahydro-pyran-3,5-diol

Guidance literature:: Multi-step reaction with 6 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

6.1: n-BuLi; CuCN / tetrahydrofuran / -78 °C

6.2: 78 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0 °C

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