(2S,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-carboxylic acid

Base Information

Chemical Name:(2S,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-carboxylic acid
CAS No.:164323-13-1
Molecular Formula:C₂₈H₃₀O₇
Molecular Weight:478.542
Hs Code.:

Synonyms:(2S,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-carboxylic acid

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Chemical Property of (2S,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-carboxylic acid

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Technology Process of (2S,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-carboxylic acid

There total 4 articles about (2S,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-carboxylic acid 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%

: 4356-80-3,34212-64-1,40653-32-5,53008-65-4,68027-27-0,73111-53-2,128184-63-4,138794-99-7,55094-38-7,641635-63-4
methyl 2,3,4-tri-O-benzyl-α-D-galactopyranoside

: 164323-13-1
(2S,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-carboxylic acid

Guidance literature:: With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; In dichloromethane; water; at 20 ℃;
DOI:10.1016/j.tet.2021.131955

Reference yield:

: 18685-19-3,40653-13-2,40653-30-3,67583-56-6,68027-26-9,73111-52-1,2595-06-4
methyl 2,3,4-tri-O-benzyl-6-O-trityl-α-D-galactopyranoside

: 164323-13-1
(2S,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-carboxylic acid

Guidance literature:: Multi-step reaction with 2 steps

1: glacial acetic acid / Heating

2: CrO₃, 3.5 M H₂SO₄ / acetone / 1.) 5 deg C; 2.) room temp., 60 min

With chromium(VI) oxide; sulfuric acid; acetic acid; In acetone;
DOI:10.1007/BF00580445

Reference yield:

: 100-39-0
benzyl bromide

: 164323-13-1
(2S,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-carboxylic acid

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) NaH / 1.) DMF, 1 h; 2.) 1 h

2: glacial acetic acid / Heating

3: CrO₃, 3.5 M H₂SO₄ / acetone / 1.) 5 deg C; 2.) room temp., 60 min

With chromium(VI) oxide; sulfuric acid; sodium hydride; acetic acid; In acetone;
DOI:10.1007/BF00580445