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

Base Information

Chemical Name:(2S,3S,4S,5R,6R)-2-Allyl-4-benzyloxy-6-hydroxymethyl-3-methyl-tetrahydro-pyran-3,5-diol
CAS No.:870135-80-1
Molecular Formula:C₁₇H₂₄O₅
Molecular Weight:308.375
Hs Code.:

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

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

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

There total 5 articles about (2S,3S,4S,5R,6R)-2-Allyl-4-benzyloxy-6-hydroxymethyl-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: 98.0%

: 870135-79-8
(4aR,6S,7S,8S,8aR)-6-allyl-8-(benzyloxy)-2,2-di-tert-butyl-7-methylhexahydropyrano[3,2-d][1,3,2]dioxasilin-7-ol

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

Guidance literature:: With triethylamine tris(hydrogen fluoride); In tetrahydrofuran; at 0 ℃;
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

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

Guidance literature:: Multi-step reaction with 4 steps

1: tetrahydrofuran / 0 °C

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

3: toluene / -78 °C

4: 98 percent / (HF)3*NEt₃ / tetrahydrofuran / 0 °C

With oxalyl dichloride; dimethyl sulfoxide; triethylamine tris(hydrogen fluoride); triethylamine; In tetrahydrofuran; dichloromethane; toluene; 2: 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

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

Guidance literature:: Multi-step reaction with 2 steps

1: toluene / -78 °C

2: 98 percent / (HF)3*NEt₃ / tetrahydrofuran / 0 °C

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