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

Base Information

• Chemical Name: 2-[(N,N'-benzyl-benzyloxycarbonyl)amino]ethyl 2,4-di-O-benzyl-3-O-(3-methoxy)benzyl-α-L-rhamnopyranoside
• CAS No.: 1314865-14-9
• Molecular Formula: C₄₅H₄₉NO₈
• Molecular Weight: 731.886

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

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

Chemical Property:

Purity/Quality:

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

There total 2 articles about 2-[(N,N'-benzyl-benzyloxycarbonyl)amino]ethyl 2,4-di-O-benzyl-3-O-(3-methoxy)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: 64.0%

2-[(N-benzyloxycarbonyl)amino]ethyl 3-O-(3-methoxy)-benzyl-α-L-rhamnopyranoside (1314865-13-8) + benzyl bromide (100-39-0) → 2-[(N,N'-benzyl-benzyloxycarbonyl)amino]ethyl 2,4-di-O-benzyl-3-O-(3-methoxy)benzyl-α-L-rhamnopyranoside (1314865-14-9)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃;

DOI:10.1021/jo200340q

Reference yield:

2-[(N-benzyloxycarbonyl)amino]ethyl L-rhamnopyranoside + 1-bromomethyl-3-methoxybenzene (874-98-6) → 2-[(N,N'-benzyl-benzyloxycarbonyl)amino]ethyl 2,4-di-O-benzyl-3-O-(3-methoxy)benzyl-α-L-rhamnopyranoside (1314865-14-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: di(n-butyl)tin oxide / methanol / 5 h / Reflux

1.2: 5 h

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C

With sodium hydride; di(n-butyl)tin oxide; In methanol; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/jo200340q

Reference yield: 69.0%

2-[(N,N'-benzyl-benzyloxycarbonyl)amino]ethyl 2,4-di-O-benzyl-3-O-(3-methoxy)benzyl-α-L-rhamnopyranoside (1314865-14-9) → 2-[(N,N'-benzyl-benzyloxycarbonyl)amino]ethyl 2,4-di-O-benzyl-α-L-rhamnopyranoside (1314865-15-0)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 0 ℃; for 0.5h;

DOI:10.1021/jo200340q

upstream raw materials:

1-bromomethyl-3-methoxybenzene

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

benzyl bromide

Downstream raw materials:

C₅₁H₆₀N₂O₁₀

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

2-[(N,N-benzyl-benzyloxycarbonyl)amino]ethyl O-(2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-α-D-glucopyranosyl)-(1→3)-2,4-di-O-benzyl-α-L-rhamnopyranoside

2-[(N,N'-benzyl-benzyloxycarbonyl)amino]ethyl O-(4-azido-3-O-benzyl-4,6-dideoxy-R-D-glucopyranosyl)-(1→3)-2,4-di-O-benzyl-R-L-rhamnopyranoside

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