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

Base Information

• Chemical Name: benzyl O-(2,3-di-O-allyl-4,6-di-O-benzyl-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
• CAS No.: 128377-00-4
• Molecular Formula: C₆₀H₆₆O₁₁
• Molecular Weight: 963.177
• Mol file: 128377-00-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about benzyl O-(2,3-di-O-allyl-4,6-di-O-benzyl-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-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: 37.0%

benzyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside (67831-42-9) + (2R,3S,4S,5R,6R)-3,4-Bis-allyloxy-5-benzyloxy-6-benzyloxymethyl-2-bromo-tetrahydro-pyran (128376-93-2) → (1R,2R,3S,4S,5R)-3,4-Bis-allyloxy-2-benzyloxy-6,8-dioxa-bicyclo[3.2.1]octane (128377-02-6) + benzyl O-(2,3-di-O-allyl-4,6-di-O-benzyl-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (128377-00-4) + benzyl O-(2,3-di-O-allyl-4,6-di-O-benzyl-α-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (128377-01-5)

Guidance literature:

With silver silicate; In dichloromethane; at 20 ℃; for 15h; molecular sieve (MS₄A), other solvents : toluene, nitromethane;

DOI:10.1016/0008-6215(90)84167-S

Reference yield:

benzyl 4,6-O-benzylidene-2,3-tri-O-benzyl-β-D-glucopyranoside (57783-66-1) → benzyl O-(2,3-di-O-allyl-4,6-di-O-benzyl-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (128377-00-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / 80 percent aq. AcOH / 1 h / 95 °C

2: 1) (Bu₃Sn)2O, 2) Bu₄NBr / 1) toluene, reflux, 2h, 2) 90 deg C, 15h

3: 40 percent / Ag silicate / CH₂Cl₂ / 15 h / 20 °C / molecular sieve (MS₄A), other solvents : toluene, nitromethane

With silver silicate; tetrabutylammomium bromide; acetic acid; bis(tri-n-butyltin)oxide; In dichloromethane;

DOI:10.1016/0008-6215(90)84167-S

Reference yield:

2,3-di-O-allyl-4,6-di-O-benzyl-D-mannopyranosyl p-nitrobenzoate (128376-99-8,128377-31-1) → benzyl O-(2,3-di-O-allyl-4,6-di-O-benzyl-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (128377-00-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.2 g / HBr / CH₂Cl₂ / 0.5 h / -15 °C

2: 40 percent / Ag silicate / CH₂Cl₂ / 15 h / 20 °C / molecular sieve (MS₄A), other solvents : toluene, nitromethane

With silver silicate; hydrogen bromide; In dichloromethane;

DOI:10.1016/0008-6215(90)84167-S

upstream raw materials:

benzyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside

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

benzyl 4,6-O-benzylidene-2,3-tri-O-benzyl-β-D-glucopyranoside

2,3-di-O-allyl-4,6-di-O-benzyl-D-mannopyranosyl p-nitrobenzoate

Downstream raw materials:

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

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

benzyl O-(4,5-di-O-benzyl-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside