3,4-di-O-benzyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranoside

Base Information

• Chemical Name: 3,4-di-O-benzyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranoside
• CAS No.: 152174-59-9
• Molecular Formula: C₂₃H₂₈O₇
• Molecular Weight: 416.471
• Mol file: 152174-59-9.mol

Synonyms:3,4-di-O-benzyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranoside

Chemical Property of 3,4-di-O-benzyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4-di-O-benzyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranoside

There total 6 articles about 3,4-di-O-benzyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranoside 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: 99.0%

3,4-Di-O-benzyl-6-O-tert-butyldiphenylsilyl-1,2-O-(methyl-orthoacetyl)-β-D-mannopyranose (163523-19-1) → 3,4-di-O-benzyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranoside (152174-59-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 2h;

Reference yield:

3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose (270087-60-0) → 3,4-di-O-benzyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranoside (152174-59-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at -78 - 20 ℃; for 3h;

DOI:10.1002/ejoc.200300483

Reference yield:

1,2-O-(1-methoxyethylidene)-β-D-mannopyranose (29073-91-4,55865-04-8,138196-19-7) → 3,4-di-O-benzyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranoside (152174-59-9)

Guidance literature:

Multi-step reaction with 3 steps

1: imidazole / tetrahydrofuran / 3 h

2: 3.29 g / NaH; TBAI / dimethylformamide / 0 - 20 °C

3: TBAF / tetrahydrofuran / 3 h / -78 - 20 °C

With 1H-imidazole; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200300483

upstream raw materials:

6-O-acetyl-3,4-di-O-benzyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose

3,4-Di-O-benzyl-6-O-tert-butyldiphenylsilyl-1,2-O-(methyl-orthoacetyl)-β-D-mannopyranose

3,4-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose

benzyl bromide

Downstream raw materials:

octyl 6-O-(2-O-acetyl-6-O-allyl-3,4-di-O-benzyl-α-D-mannopyranosyl)-2,3,4-tri-O-benzyl-β-D-glucopyranoside

octyl 6-O-(6-O-allyl-3,4-di-O-benzyl-α-D-mannopyranosyl)-2,3,4-tri-O-benzyl-β-D-glucopyranoside

Acetic acid (3S,4S,5R,6R)-6-allyloxymethyl-4,5-bis-benzyloxy-2-chloro-tetrahydro-pyran-3-yl ester

Acetic acid (2S,3S,4S,5R,6R)-6-[3-((2S,3S,4S,5R,6R)-3-acetoxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ureidomethyl]-4,5-bis-benzyloxy-2-[3-(9H-fluoren-9-ylmethoxycarbonylamino)-propoxy]-tetrahydro-pyran-3-yl ester