methyl 3,4,6-tri-O-benzyl-β-D-mannopyranosyl-(1->6)-2,3-di-O-benzyl-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 3,4,6-tri-O-benzyl-β-D-mannopyranosyl-(1->6)-2,3-di-O-benzyl-α-D-glucopyranoside
• CAS No.: 173910-83-3
• Molecular Formula: C₄₈H₅₄O₁₁
• Molecular Weight: 806.95
• Mol file: 173910-83-3.mol

Synonyms:methyl 3,4,6-tri-O-benzyl-β-D-mannopyranosyl-(1->6)-2,3-di-O-benzyl-α-D-glucopyranoside

Chemical Property of methyl 3,4,6-tri-O-benzyl-β-D-mannopyranosyl-(1->6)-2,3-di-O-benzyl-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3,4,6-tri-O-benzyl-β-D-mannopyranosyl-(1->6)-2,3-di-O-benzyl-α-D-glucopyranoside

There total 3 articles about methyl 3,4,6-tri-O-benzyl-β-D-mannopyranosyl-(1->6)-2,3-di-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: 98.0%

(1S,2R,3R,4aR,6aS,8R,9S,10S,10aS,13aS)-1,2,9,10-Tetrakis-benzyloxy-3-benzyloxymethyl-8-methoxy-12,12-dimethyl-decahydro-4,5,7,11,13-pentaoxa-12-sila-dibenzo[a,e]cyclononene → methyl 3,4,6-tri-O-benzyl-β-D-mannopyranosyl-(1->6)-2,3-di-O-benzyl-α-D-glucopyranoside (173910-83-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 1h; Ambient temperature;

DOI:10.1021/ja9532291

Reference yield: 29.0%

3,4,6-tri-O-benzyl-2-O-(2-iodo-1-(methyl 2,3-di-O-benzyl-α-D-glucopyranosid-6-O-yl)-propyl)-α-D-mannopyranosyl fluoride → methyl 3,4,6-tri-O-benzyl-β-D-mannopyranosyl-(1->6)-2,3-di-O-benzyl-α-D-glucopyranoside (173910-83-3) + methyl 3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->4)-2,3-di-O-benzyl-α-D-glucopyranoside

Guidance literature:

3,4,6-tri-O-benzyl-2-O-(2-iodo-1-(methyl 2,3-di-O-benzyl-α-D-glucopyranosid-6-O-yl)-propyl)-α-D-mannopyranosyl fluoride; With 4 A molecular sieve; silver trifluoromethanesulfonate; tin(ll) chloride; 2,6-di-tert-butyl-4-methylpyridine; In 1,2-dichloro-ethane; at 50 ℃; for 22h;

With trifluoroacetic acid; In tetrahydrofuran; methanol; water; at 20 ℃; for 72h;

DOI:10.1016/j.tetasy.2004.09.003

Reference yield:

2-O-prop-1'-enyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl fluoride (358351-64-1) → methyl 3,4,6-tri-O-benzyl-β-D-mannopyranosyl-(1->6)-2,3-di-O-benzyl-α-D-glucopyranoside (173910-83-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 73 percent / N-iodosuccinimide; molecular sieves 4 Angstroem / 1,2-dichloro-ethane / -40 - 20 °C

2.1: tin(II) chloride; molecular sieves 4 Angstroem; silver(I) trifluoromethanesulfonate / 2,6-di-tert-butyl-4-methylpyridine / 1,2-dichloro-ethane / 22 h / 50 °C

2.2: 12 percent / trifluoroacetic acid / tetrahydrofuran; methanol; H₂O / 72 h / 20 °C

With N-iodo-succinimide; 4 A molecular sieve; silver trifluoromethanesulfonate; tin(ll) chloride; 2,6-di-tert-butyl-4-methylpyridine; In 1,2-dichloro-ethane;

DOI:10.1016/j.tetasy.2004.09.003

upstream raw materials:

2-O-prop-1'-enyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl fluoride

Downstream raw materials:

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