2-[(N-benzyloxycarbonyl)amino]ethyl 3,4-di-O-benzyl-α-L-rhamnopyranoside

Base Information

• Chemical Name: 2-[(N-benzyloxycarbonyl)amino]ethyl 3,4-di-O-benzyl-α-L-rhamnopyranoside
• CAS No.: 1384442-69-6
• Molecular Formula: C₃₀H₃₅NO₇
• Molecular Weight: 521.61

Synonyms:2-[(N-benzyloxycarbonyl)amino]ethyl 3,4-di-O-benzyl-α-L-rhamnopyranoside

Chemical Property of 2-[(N-benzyloxycarbonyl)amino]ethyl 3,4-di-O-benzyl-α-L-rhamnopyranoside

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Technology Process of 2-[(N-benzyloxycarbonyl)amino]ethyl 3,4-di-O-benzyl-α-L-rhamnopyranoside

There total 9 articles about 2-[(N-benzyloxycarbonyl)amino]ethyl 3,4-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: 100.0%

2-[(N-benzyloxycarbonyl)amino]ethyl 2-O-benzoyl-3,4-di-O-benzyl-α-L-rhamnopyranoside (1384442-71-0) → 2-[(N-benzyloxycarbonyl)amino]ethyl 3,4-di-O-benzyl-α-L-rhamnopyranoside (1384442-69-6)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃;

DOI:10.1016/j.carres.2012.01.007

Reference yield: 95.0%

2-(carbobenzyloxy)aminoethyl 2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranoside → 2-[(N-benzyloxycarbonyl)amino]ethyl 3,4-di-O-benzyl-α-L-rhamnopyranoside (1384442-69-6)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 2h;

DOI:10.1039/c4ra06989g

Reference yield:

benzyl 2-hydroxyethylcarbamate (77987-49-6) → 2-[(N-benzyloxycarbonyl)amino]ethyl 3,4-di-O-benzyl-α-L-rhamnopyranoside (1384442-69-6)

Guidance literature:

Multi-step reaction with 2 steps

1: N-iodo-succinimide; silver trifluoromethanesulfonate / dichloromethane / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere

2: sodium methylate / methanol / 20 °C

With N-iodo-succinimide; sodium methylate; silver trifluoromethanesulfonate; In methanol; dichloromethane;

DOI:10.1016/j.carres.2012.01.007

upstream raw materials:

5-tert-butyl-2-methylphenyl 4-O-benzyl-2-O-benzoyl-1-thio-α-L-rhamnopyranoside

2-methyl-5-tert-butylphenyl 2-O-benzoyl-3,4-di-O-benzyl-1-thio-α-L-rhamnopyranoside

2-[(N-benzyloxycarbonyl)amino]ethyl 2-O-benzoyl-3,4-di-O-benzyl-α-L-rhamnopyranoside

2-methyl-5-tert-butylphenyl 4-O-benzyl-1-thio-α-L-rhamnopyranoside

Downstream raw materials:

2-[(N-benzyloxycarbonyl)amino]ethyl 2-O-benzoyl-4-O-benzyl-3-O-chloroacetyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside

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