(2S,3S,4S,5S,6S)-3,4,5,6-Tetrakis-benzyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2S,3S,4S,5S,6S)-3,4,5,6-Tetrakis-benzyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS No.: 253596-63-3
• Molecular Formula: C₃₅H₃₆O₇
• Molecular Weight: 568.667
• Mol file: 253596-63-3.mol

Synonyms:(2S,3S,4S,5S,6S)-3,4,5,6-Tetrakis-benzyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property of (2S,3S,4S,5S,6S)-3,4,5,6-Tetrakis-benzyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S,5S,6S)-3,4,5,6-Tetrakis-benzyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 2 articles about (2S,3S,4S,5S,6S)-3,4,5,6-Tetrakis-benzyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester 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:

benzyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside (57783-76-3) → (2S,3S,4S,5S,6S)-3,4,5,6-Tetrakis-benzyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester (253596-63-3)

Guidance literature:

Multi-step reaction with 2 steps

1: CrO₃; H₂SO₄

With chromium(VI) oxide; sulfuric acid; 1: Oxidation / 2: Methylation;

DOI:10.1080/07328309908544046

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + benzyl 2,3,4-tri-O-benzyl-α-D-mannopyranuronic acid (858352-14-4) → (2S,3S,4S,5S,6S)-3,4,5,6-Tetrakis-benzyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester (253596-63-3)

Guidance literature:

DOI:10.1080/07328309908544046

Reference yield: 75.0%

(2S,3S,4S,5S,6S)-3,4,5,6-Tetrakis-benzyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester (253596-63-3) + dimethyl methane phosphonate (756-79-6) → dimethyl (benzyl 2,3,4-tri-O-benzyl-α-D-manno-heptopyranos-6-ulos-7-yl)phosphonate (222417-79-0)

Guidance literature:

dimethyl methane phosphonate; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h;

(2S,3S,4S,5S,6S)-3,4,5,6-Tetrakis-benzyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester; In tetrahydrofuran; hexane; at -78 - 20 ℃;

DOI:10.1080/07328309908544046

upstream raw materials:

diazomethane

benzyl 2,3,4-tri-O-benzyl-α-D-mannopyranuronic acid

benzyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside

Downstream raw materials:

dimethyl (benzyl 2,3,4-tri-O-benzyl-α-D-manno-heptopyranos-6-ulos-7-yl)phosphonate

benzyl 2,3,4-tri-O-benzyl-α-D-glycero-D-manno-heptopyranoside

3-O-benzyl-5-deoxy-5-C-[benzyl 2,3,4-tri-O-benzyl-7-deoxy-α-D-manno-heptopyranosid-6-ulose-7(E)-ylidene]-1,2-O-isopropylidene-α-D-xylofuranose

3-O-benzyl-5-deoxy-5-C-[benzyl 2,3,4-tri-O-benzyl-7-deoxy-D-glycero-α-D-manno-heptopyranosid-7(E)-ylidene]-1,2-O-isopropylidene-α-D-xylofuranose