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

Base Information

Chemical Name:2-[(N,N'-benzyl-benzyloxycarbonyl)amino]ethyl O-(4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-R-D-glucopyranosyl)-(1→3)-2,4-di-O-benzyl-R-L-rhamnopyranoside
CAS No.:1314865-18-3
Molecular Formula:C₅₁H₅₈N₄O₁₀
Molecular Weight:887.042
Hs Code.:

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

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

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

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

There total 7 articles about 2-[(N,N'-benzyl-benzyloxycarbonyl)amino]ethyl O-(4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-R-D-glucopyranosyl)-(1→3)-2,4-di-O-benzyl-R-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: 62.0%

: 1314865-17-2
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

: 74-88-4
methyl iodide

: 1314865-18-3
2-[(N,N'-benzyl-benzyloxycarbonyl)amino]ethyl O-(4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-R-D-glucopyranosyl)-(1→3)-2,4-di-O-benzyl-R-L-rhamnopyranoside

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃;
DOI:10.1021/jo200340q

Reference yield:

: 2-[(N-benzyloxycarbonyl)amino]ethyl L-rhamnopyranoside

: 1314865-18-3
2-[(N,N'-benzyl-benzyloxycarbonyl)amino]ethyl O-(4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-R-D-glucopyranosyl)-(1→3)-2,4-di-O-benzyl-R-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 6 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

3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 0.5 h / 0 °C

4.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.5 h / -40 °C / Molecular sieve; Inert atmosphere

5.1: sodium methylate / methanol / 12 h / 20 °C

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

With trimethylsilyl trifluoromethanesulfonate; sodium methylate; sodium hydride; di(n-butyl)tin oxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;
DOI:10.1021/jo200340q

Reference yield:

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

: 1314865-18-3
2-[(N,N'-benzyl-benzyloxycarbonyl)amino]ethyl O-(4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-R-D-glucopyranosyl)-(1→3)-2,4-di-O-benzyl-R-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 0.5 h / 0 °C

2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.5 h / -40 °C / Molecular sieve; Inert atmosphere

3: sodium methylate / methanol / 12 h / 20 °C

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

With trimethylsilyl trifluoromethanesulfonate; sodium methylate; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;
DOI:10.1021/jo200340q