O-(2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-(1-4)-O-(3,6-di-O-benzyl-2-<(benzyloxycarbonyl)amino>-2-deoxy-α-D-glucopyranosyl)-(1-6)-1,2,3,4,5-penta-O-acetyl-D-myo-inositol

Base Information

• Chemical Name: O-(2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-(1-4)-O-(3,6-di-O-benzyl-2-<(benzyloxycarbonyl)amino>-2-deoxy-α-D-glucopyranosyl)-(1-6)-1,2,3,4,5-penta-O-acetyl-D-myo-inositol
• CAS No.: 123487-59-2
• Molecular Formula: C₇₁H₇₉NO₂₂
• Molecular Weight: 1298.4
• Mol file: 123487-59-2.mol

Synonyms:O-(2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-(1-4)-O-(3,6-di-O-benzyl-2-<(benzyloxycarbonyl)amino>-2-deoxy-α-D-glucopyranosyl)-(1-6)-1,2,3,4,5-penta-O-acetyl-D-myo-inositol

Chemical Property of O-(2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-(1-4)-O-(3,6-di-O-benzyl-2-<(benzyloxycarbonyl)amino>-2-deoxy-α-D-glucopyranosyl)-(1-6)-1,2,3,4,5-penta-O-acetyl-D-myo-inositol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-(2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-(1-4)-O-(3,6-di-O-benzyl-2-<(benzyloxycarbonyl)amino>-2-deoxy-α-D-glucopyranosyl)-(1-6)-1,2,3,4,5-penta-O-acetyl-D-myo-inositol

There total 8 articles about O-(2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-(1-4)-O-(3,6-di-O-benzyl-2-<(benzyloxycarbonyl)amino>-2-deoxy-α-D-glucopyranosyl)-(1-6)-1,2,3,4,5-penta-O-acetyl-D-myo-inositol 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:

C77H93NO22Si → O-(2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-(1-4)-O-(3,6-di-O-benzyl-2-<(benzyloxycarbonyl)amino>-2-deoxy-α-D-glucopyranosyl)-(1-6)-1,2,3,4,5-penta-O-acetyl-D-myo-inositol (123487-59-2)

Guidance literature:

With pyridine hydrogenfluoride; In tetrahydrofuran; for 2h; Yield given; Ambient temperature;

DOI:10.1021/ja00110a011

Reference yield:

D-Mannose (3458-28-4) → O-(2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-(1-4)-O-(3,6-di-O-benzyl-2-<(benzyloxycarbonyl)amino>-2-deoxy-α-D-glucopyranosyl)-(1-6)-1,2,3,4,5-penta-O-acetyl-D-myo-inositol (123487-59-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 65 percent / camphorsulfonic acid / dimethylsulfoxide / 24 h / 90 °C

2: Et₃N, DMAP / CH₂Cl₂

3: NaH / dimethylformamide

4: 1.) NIS, TfOH, 4A molecular sieves, 2.) HF, pyridine / 1.) CH₂Cl₂, 2.) THF

With pyridine; dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; camphor-10-sulfonic acid; hydrogen fluoride; sodium hydride; triethylamine; In dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/ja00204a049

Reference yield:

(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-(pent-4-en-1-yloxy)tetrahydro-2H-pyran-3,4,5-triol (125631-33-6,125647-51-0,132871-89-7,132871-95-5,132871-96-6,123487-65-0) → O-(2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-(1-4)-O-(3,6-di-O-benzyl-2-<(benzyloxycarbonyl)amino>-2-deoxy-α-D-glucopyranosyl)-(1-6)-1,2,3,4,5-penta-O-acetyl-D-myo-inositol (123487-59-2)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N, DMAP / CH₂Cl₂

2: NaH / dimethylformamide

3: 1.) NIS, TfOH, 4A molecular sieves, 2.) HF, pyridine / 1.) CH₂Cl₂, 2.) THF

With pyridine; dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; hydrogen fluoride; sodium hydride; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00204a049

upstream raw materials:

tert-Butyl-diphenyl-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-pent-4-enyloxy-tetrahydro-pyran-2-ylmethoxy)-silane

1,2,3,4,5-penta-O-acetyl-6-O-(3,6-di-O-benzyl-2-<(benzyloxycarbonyl)amino>-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol

D-Mannose

1,2,3,4,5-penta-O-acetyl-D-myo-inositol

Downstream raw materials:

O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1-2)-O-(3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-(1-6)-O-(2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-(1-4)-O-(3,6-di-O-benzyl-2-<(benzyloxycarbonyl)amino>-2-deoxy-α-D-glucopyranosyl)-(1-6)-1,2,3,4,5-pe

O-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl)-(1-2)-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1-6)-O-(2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-(1-4)-O-(3,6-di-O-benzyl-2-<(benzyloxycarbonyl)amino>-2-deoxy-α-D-glucopyranosyl)-(1-6)-1,2,3,4,5-pent

O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1-6)-O-(2,3,4-tri-O-benzyl-α-D-mannopyranosyl)-(1-4)-O-(3,6-di-O-benzyl-2-<(benzyloxycarbonyl)amino>-2-deoxy-α-D-glucopyranosyl)-(1-6)-1,2,3,4,5-penta-O-acetyl-D-myo-inositol