methyl (3,4,6-tri-O-acetyl-2-amino-2-deoxy-α-D-glucopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-4,6-O-benzylidene-3-deoxy-α-D-xylo-hexopyranoside

Base Information

• Chemical Name: methyl (3,4,6-tri-O-acetyl-2-amino-2-deoxy-α-D-glucopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-4,6-O-benzylidene-3-deoxy-α-D-xylo-hexopyranoside
• CAS No.: 218279-76-6
• Molecular Formula: C₆₆H₇₁NO₂₄
• Molecular Weight: 1262.28
• Mol file: 218279-76-6.mol

Synonyms:methyl (3,4,6-tri-O-acetyl-2-amino-2-deoxy-α-D-glucopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-4,6-O-benzylidene-3-deoxy-α-D-xylo-hexopyranoside

Chemical Property of methyl (3,4,6-tri-O-acetyl-2-amino-2-deoxy-α-D-glucopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-4,6-O-benzylidene-3-deoxy-α-D-xylo-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (3,4,6-tri-O-acetyl-2-amino-2-deoxy-α-D-glucopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-4,6-O-benzylidene-3-deoxy-α-D-xylo-hexopyranoside

There total 8 articles about methyl (3,4,6-tri-O-acetyl-2-amino-2-deoxy-α-D-glucopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-4,6-O-benzylidene-3-deoxy-α-D-xylo-hexopyranoside 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: 79.0%

methyl (3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-4,6-O-benzylidene-3-deoxy-α-D-xylo-hexopyranoside (218279-75-5) → methyl (3,4,6-tri-O-acetyl-2-amino-2-deoxy-α-D-glucopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-4,6-O-benzylidene-3-deoxy-α-D-xylo-hexopyranoside (218279-76-6)

Guidance literature:

With triphenylphosphine; In dichloromethane; at 35 ℃; for 24h;

DOI:10.1016/S0008-6215(98)00216-X

Reference yield:

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl chloride (67817-20-3) → methyl (3,4,6-tri-O-acetyl-2-amino-2-deoxy-α-D-glucopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-4,6-O-benzylidene-3-deoxy-α-D-xylo-hexopyranoside (218279-76-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 69 percent / 2,6-di-tert-butyl-4-methylpyridine, AgOTf / CH₂Cl₂ / 1 h / 0 °C

2: 79 percent / triphenylphosphine / CH₂Cl₂ / 24 h / 35 °C

With 2,6-di-tert-butyl-4-methylpyridine; silver trifluoromethanesulfonate; triphenylphosphine; In dichloromethane;

DOI:10.1016/S0008-6215(98)00216-X

Reference yield:

2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranosyl chloride (146934-39-6) → methyl (3,4,6-tri-O-acetyl-2-amino-2-deoxy-α-D-glucopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-4,6-O-benzylidene-3-deoxy-α-D-xylo-hexopyranoside (218279-76-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 84 percent / 2,6-di-tert-butyl-4-methylpyridine, silver trifluoromethanesulfonate / CH₂Cl₂ / -15 deg C, 30 min, then -> room temp., 2 h

2: 66 percent / α,α-dichloromethyl methyl ether, ZnCl2*Et2O / CH2Cl2 / 1.25 h / 60 °C

3: 80 percent / 2,6-di-tert-butyl-4-methylpyridine, AgOTf / CH₂Cl₂ / 1.5 h / -15 - 0 °C

4: 88 percent / thiourea, sym-collidine / CH₂Cl₂; methanol / 36 h / 25 °C

5: 69 percent / 2,6-di-tert-butyl-4-methylpyridine, AgOTf / CH₂Cl₂ / 1 h / 0 °C

6: 79 percent / triphenylphosphine / CH₂Cl₂ / 24 h / 35 °C

With 2,4,6-trimethyl-pyridine; 2,6-di-tert-butyl-4-methylpyridine; zinc chloride diethyl ether; Dichloromethyl methyl ether; silver trifluoromethanesulfonate; thiourea; triphenylphosphine; In methanol; dichloromethane;

DOI:10.1016/S0008-6215(98)00216-X

upstream raw materials:

methyl (3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-4,6-O-benzylidene-3-deoxy-α-D-xylo-hexopyranoside

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl chloride

2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranosyl chloride

methyl 2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranoside

Downstream raw materials:

methyl (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-3-deoxy-α-D-xylo-hexopyranoside

methyl (2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->2)-4,6-O-benzylidene-3-deoxy-α-D-xylo-hexopyranoside