methyl O-(4,6-di-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl)-(1-3)-2,4-di-O-benzyl-α-L-rhamnopyranoside

Base Information

• Chemical Name: methyl O-(4,6-di-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl)-(1-3)-2,4-di-O-benzyl-α-L-rhamnopyranoside
• CAS No.: 211806-79-0
• Molecular Formula: C₃₃H₄₀ClN₃O₁₂
• Molecular Weight: 706.146
• Mol file: 211806-79-0.mol

Synonyms:methyl O-(4,6-di-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl)-(1-3)-2,4-di-O-benzyl-α-L-rhamnopyranoside

Chemical Property of methyl O-(4,6-di-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl)-(1-3)-2,4-di-O-benzyl-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl O-(4,6-di-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl)-(1-3)-2,4-di-O-benzyl-α-L-rhamnopyranoside

There total 5 articles about methyl O-(4,6-di-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl)-(1-3)-2,4-di-O-benzyl-α-L-rhamnopyranoside 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:

methyl O-(2-azido-2-deoxy-α-D-glucopyranosyl)-(1-3)-2,4-di-O-benzyl-α-L-rhamnopyranoside (211806-78-9) → methyl O-(4,6-di-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl)-(1-3)-2,4-di-O-benzyl-α-L-rhamnopyranoside (211806-79-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 10-camphorsulfonic acid / dimethylformamide / 1 h / 23 °C

2: pyridine / 0.5 h / 0 °C

3: 54percent HBF₄ / methanol; diethyl ether / 1 h / 0 °C

4: pyridine / 0 °C

With pyridine; tetrafluoroboric acid; (1S)-10-camphorsulfonic acid; In methanol; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(98)00047-0

Reference yield:

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-azido-6-((2R,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-tetrahydro-pyran-4-yl ester → methyl O-(4,6-di-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl)-(1-3)-2,4-di-O-benzyl-α-L-rhamnopyranoside (211806-79-0)

Guidance literature:

Multi-step reaction with 5 steps

1: NaOMe / methanol / 4 h

2: 10-camphorsulfonic acid / dimethylformamide / 1 h / 23 °C

3: pyridine / 0.5 h / 0 °C

4: 54percent HBF₄ / methanol; diethyl ether / 1 h / 0 °C

5: pyridine / 0 °C

With pyridine; tetrafluoroboric acid; (1S)-10-camphorsulfonic acid; sodium methylate; In methanol; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(98)00047-0

Reference yield:

(4aR,6R,7R,8R,8aS)-7-Azido-6-((2R,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol → methyl O-(4,6-di-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl)-(1-3)-2,4-di-O-benzyl-α-L-rhamnopyranoside (211806-79-0)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 0.5 h / 0 °C

2: 54percent HBF₄ / methanol; diethyl ether / 1 h / 0 °C

3: pyridine / 0 °C

With pyridine; tetrafluoroboric acid; In methanol; diethyl ether;

DOI:10.1016/S0008-6215(98)00047-0

upstream raw materials:

acetic anhydride

methyl O-(2-azido-2-deoxy-α-D-glucopyranosyl)-(1-3)-2,4-di-O-benzyl-α-L-rhamnopyranoside

Downstream raw materials:

methyl O-(4,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1-3)-2,4-di-O-benzyl-α-L-rhamnopyranoside

methyl O-(3,4,6-tri-O-benzyl-α-D-(1-13C)-galactopyranosyl)-(1-3)-O-(4,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1-3)-2,4-di-O-benzyl-α-L-rhamnopyranoside

methyl O-[3,4,6-tri-O-benzyl-2-O-(4-methoxybenzyl)-α-D-(1-13C)-galactopyranosyl]-(1-3)-O-(4,6-di-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1-3)-2,4-di-O-benzyl-α-L-rhamnopyranoside