methyl 2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-glucopyranoside
• CAS No.: 129948-14-7
• Molecular Formula: C₄₂H₅₀O₁₅
• Molecular Weight: 794.85
• Mol file: 129948-14-7.mol

Synonyms:methyl 2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-glucopyranoside

Chemical Property of methyl 2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-glucopyranoside

There total 9 articles about methyl 2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-glucopyranoside 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: 84.0%

methyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside (20672-67-7) + S-ethyl 2,3,4,6-tetra-O-acetyl-1-deoxy-1-thio-α-D-mannopyranoside (32934-24-0,41670-79-5,52645-73-5,55722-49-1,79389-52-9,99031-86-4,125354-48-5,126187-25-5) → methyl 3,4,6-tri-O-benzyl-2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside (129948-14-7,131283-77-7)

Guidance literature:

methyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside; S-ethyl 2,3,4,6-tetra-O-acetyl-1-deoxy-1-thio-α-D-mannopyranoside; With rhodium (II) octanoate dimer; methyl 2-(4-chlorophenyl)-2-diazoacetate; In dichloromethane; at 0 ℃; for 1h; Molecular sieve;

With trifluorormethanesulfonic acid; In dichloromethane; at 0 ℃; for 1h; Molecular sieve;

DOI:10.1021/jacs.9b04619

Reference yield: 81.0%

(2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-ol (20672-67-7,40246-25-1,40246-30-8,73415-91-5,73445-27-9,81086-90-0,148888-64-6) + 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl chloride (572-10-1,4451-35-8,4451-36-9,14227-52-2,14227-87-3,14227-88-4,14257-40-0,17081-03-7,19186-60-8,57237-01-1,65982-17-4,65982-18-5,65982-19-6,66966-08-3,144299-57-0) → methyl 2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-glucopyranoside (129948-14-7)

Guidance literature:

With silver trifluoromethanesulfonate; molecular sieve; In dichloromethane; toluene; at -20 ℃; for 0.833333h;

Reference yield:

3,4,6-tri-O-acetyl-1,2-O-(1-ethoxyethylidene)-α-D-galactopyranose (3254-15-7) → Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester (129948-14-7,131283-77-7)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium methoxide / methanol

2: silver oxide / dimethylformamide / 18 h

3: 1.) p-toluenesulfonic acid, 2.) sodium methoxide / 1.) methanol, 30 min, 50 deg C

4: silver carbonate / CH₂Cl₂ / 2 h

With sodium methylate; toluene-4-sulfonic acid; silver carbonate; silver(l) oxide; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)80790-9

upstream raw materials:

(2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-ol

2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl chloride

methyl 3,4,6-tri-O-benzyl-β-D-galactopyranoside

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

Downstream raw materials:

methyl 3,4,6-tri-O-benzyl-2-O-α-D-mannopyranosyl-α-D-mannopyranoside

(2S,3R,4S,5R,6R)-2-((2R,3R,4S,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol