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

Base Information

• Chemical Name: methyl 3-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-6-O-(3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranosyl)-2,4-di-O-benzyl-α-D-mannopyranoside
• CAS No.: 80738-57-4
• Molecular Formula: C₇₄H₈₂O₁₉
• Molecular Weight: 1275.45

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

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

Chemical Property:

Purity/Quality:

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

There total 6 articles about methyl 3-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-6-O-(3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranosyl)-2,4-di-O-benzyl-α-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: 98.0%

methyl 3-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-2,4-di-O-benzyl-α-D-mannopyranoside (1096120-53-4) + phenyl 3,6-di-O-acetyl-2,4-di-O-benzyl-1-thio-α-D-mannopyranoside (213998-08-4) → methyl 3-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-6-O-(3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranosyl)-2,4-di-O-benzyl-α-D-mannopyranoside (80738-57-4)

Guidance literature:

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; stereoselective reaction; Sonication;

DOI:10.1021/jo8019835

Reference yield: 90.7%

2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl chloride (65827-59-0) + Acetic acid (2R,3R,4S,5S,6S)-2-acetoxymethyl-3,5-bis-benzyloxy-6-((2R,3S,4S,5S,6S)-3,5-bis-benzyloxy-4-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-4-yl ester (80738-51-8) → 2-O-acetyl-3,4,6-tri-O-benzyl-1,5-anhydro-D-arabino-hex-1-enitol (80738-62-1) + methyl 3-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-6-O-(3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranosyl)-2,4-di-O-benzyl-α-D-mannopyranoside (80738-57-4)

Guidance literature:

With silver trifluoromethanesulfonate; tetramethylurea; In dichloromethane; at -15 - 20 ℃; for 19h; Yields of byproduct given;

DOI:10.1016/S0040-4020(01)92346-4

Reference yield:

methyl 2,4-di-O-benzyl-α-D-mannopyranoside (58341-67-6,67381-34-4,86172-91-0,86342-19-0,67381-29-7) → methyl 3-O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-6-O-(3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranosyl)-2,4-di-O-benzyl-α-D-mannopyranoside (80738-57-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 54.4 percent / AgSO₃CF₃, Me₂NCONMe₂ / CH₂Cl₂ / 21 h / -5 - 25 °C

2: 90.7 percent / AgSO₃CF₃, Me₂NCONMe₂ / CH₂Cl₂ / 19 h / -15 - 20 °C

With silver trifluoromethanesulfonate; tetramethylurea; In dichloromethane;

DOI:10.1016/S0040-4020(01)92346-4

upstream raw materials:

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

Acetic acid (2R,3R,4S,5S,6S)-2-acetoxymethyl-3,5-bis-benzyloxy-6-((2R,3S,4S,5S,6S)-3,5-bis-benzyloxy-4-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-4-yl ester

methyl 2,4-di-O-benzyl-α-D-mannopyranoside

1,3,6-tri-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranose

Downstream raw materials:

methyl 3,6-di-O-(α-D-mannopyranosyl)-α-D-mannopyranoside

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

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