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

Base Information

Chemical Name:(2R,3R,4S,5R,6R)-methyl 3,4,5-tris(benzyloxy)-6-((tert-butyldimethylsilyloxy)methyl)-tetrahydro-2H-pyran-2-carboxylate
CAS No.:177213-24-0
Molecular Formula:C₃₅H₄₆O₇Si
Molecular Weight:606.832
Hs Code.:

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

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

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

There total 4 articles about (2R,3R,4S,5R,6R)-methyl 3,4,5-tris(benzyloxy)-6-((tert-butyldimethylsilyloxy)methyl)-tetrahydro-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: 83.0%

: 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

: 177213-24-0
(2R,3R,4S,5R,6R)-methyl 3,4,5-tris(benzyloxy)-6-((tert-butyldimethylsilyloxy)methyl)-tetrahydro-2H-pyran-2-carboxylate

Guidance literature:: With silver(l) oxide; In N,N-dimethyl-formamide; at 25 ℃; for 20h;
DOI:10.1016/0040-4039(95)00121-R

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

: 177213-24-0
(2R,3R,4S,5R,6R)-methyl 3,4,5-tris(benzyloxy)-6-((tert-butyldimethylsilyloxy)methyl)-tetrahydro-2H-pyran-2-carboxylate

: (2R,3R,4S,5R,6R)-benzyl 3,4,5-tris(benzyloxy)-6-((tert-butyldimethylsilyloxy)methyl)-tetrahydro-2H-pyran-2-carboxylate

Guidance literature:: With silver(l) oxide; In N,N-dimethyl-formamide; for 20h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Ambient temperature;
DOI:10.1016/0040-4039(96)00327-9

Reference yield:

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

: 177213-24-0
(2R,3R,4S,5R,6R)-methyl 3,4,5-tris(benzyloxy)-6-((tert-butyldimethylsilyloxy)methyl)-tetrahydro-2H-pyran-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 83 percent / imidazole / dimethylformamide / 2 h / 20 °C

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

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