(2R,3R,4S,5R,6R)-methyl 3,4,5-tris(benzyloxy)-tetrahydro-6-(hydroxymethyl)-2H-pyran-2-carboxylate

Base Information

Chemical Name:(2R,3R,4S,5R,6R)-methyl 3,4,5-tris(benzyloxy)-tetrahydro-6-(hydroxymethyl)-2H-pyran-2-carboxylate
CAS No.:177213-12-6
Molecular Formula:C₂₉H₃₂O₇
Molecular Weight:492.569
Hs Code.:

Synonyms:(2R,3R,4S,5R,6R)-methyl 3,4,5-tris(benzyloxy)-tetrahydro-6-(hydroxymethyl)-2H-pyran-2-carboxylate

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Chemical Property of (2R,3R,4S,5R,6R)-methyl 3,4,5-tris(benzyloxy)-tetrahydro-6-(hydroxymethyl)-2H-pyran-2-carboxylate

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Technology Process of (2R,3R,4S,5R,6R)-methyl 3,4,5-tris(benzyloxy)-tetrahydro-6-(hydroxymethyl)-2H-pyran-2-carboxylate

There total 6 articles about (2R,3R,4S,5R,6R)-methyl 3,4,5-tris(benzyloxy)-tetrahydro-6-(hydroxymethyl)-2H-pyran-2-carboxylate 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: 96.0%

: C₃₇H₄₀O₈

: 177213-12-6
(2R,3R,4S,5R,6R)-methyl 3,4,5-tris(benzyloxy)-tetrahydro-6-(hydroxymethyl)-2H-pyran-2-carboxylate

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone;
DOI:10.1002/ejoc.200600993

Reference yield:

: 100-39-0
benzyl bromide

: 177213-11-5
(2R,3R,4S,5R,6R)-methyl tetrahydro-3,4,5-trihydroxy-6-((tert-butyldimethylsilyloxy)methyl)-2H-pyran-2-carboxylate

: 177213-12-6
(2R,3R,4S,5R,6R)-methyl 3,4,5-tris(benzyloxy)-tetrahydro-6-(hydroxymethyl)-2H-pyran-2-carboxylate

Guidance literature:: benzyl bromide; (2R,3R,4S,5R,6R)-methyl tetrahydro-3,4,5-trihydroxy-6-((tert-butyldimethylsilyloxy)methyl)-2H-pyran-2-carboxylate; With silver(l) oxide; In N,N-dimethyl-formamide; at 20 ℃; for 20h;

With acetic acid; In tetrahydrofuran; water; at 20 ℃; for 15h;
DOI:10.1016/j.tet.2006.05.080

Reference yield:

: 57039-38-0
(2R,3R,4S,5S,6R)-methyl tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-2-carboxylate

: 177213-12-6
(2R,3R,4S,5R,6R)-methyl 3,4,5-tris(benzyloxy)-tetrahydro-6-(hydroxymethyl)-2H-pyran-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 83 percent / imidazole / dimethylformamide / 2 h / 20 °C

2.1: Ag₂O / dimethylformamide / 20 h / 20 °C

2.2: 7.60 g / acetic acid / H₂O; tetrahydrofuran / 15 h / 20 °C

With 1H-imidazole; silver(l) oxide; In N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2006.05.080