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

Base Information

• Chemical Name: 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
• CAS No.: 218279-77-7
• Molecular Formula: C₆₈H₇₃NO₂₅
• Molecular Weight: 1304.32
• Mol file: 218279-77-7.mol

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 9 articles about 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 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:

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl chloride (67817-20-3) → 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 (218279-77-7)

Guidance literature:

Multi-step reaction with 3 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

3: pyridine / Ambient temperature

With pyridine; 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 (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 (218279-77-7)

Guidance literature:

Multi-step reaction with 7 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

7: pyridine / Ambient temperature

With pyridine; 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

Reference yield:

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 (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 (218279-77-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / triphenylphosphine / CH₂Cl₂ / 24 h / 35 °C

2: pyridine / Ambient temperature

With pyridine; triphenylphosphine; In dichloromethane;

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

upstream raw materials:

acetic anhydride

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

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

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