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

Base Information

Chemical Name:2-[(N-benzyloxycarbonyl)amino]ethyl 4-azido-4,6-dideoxy-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside
CAS No.:1384442-83-4
Molecular Formula:C₃₆H₄₂N₄O₁₁
Molecular Weight:706.75
Hs Code.:

Synonyms:2-[(N-benzyloxycarbonyl)amino]ethyl 4-azido-4,6-dideoxy-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

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Chemical Property of 2-[(N-benzyloxycarbonyl)amino]ethyl 4-azido-4,6-dideoxy-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

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Technology Process of 2-[(N-benzyloxycarbonyl)amino]ethyl 4-azido-4,6-dideoxy-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

There total 6 articles about 2-[(N-benzyloxycarbonyl)amino]ethyl 4-azido-4,6-dideoxy-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-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: 26.0%

: 1384442-79-8
2-[(N-benzyloxycarbonyl)amino]ethyl 4-azido-3-O-benzoyl-4,6-dideoxy-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

: 74-88-4
methyl iodide

: 1384442-82-3
2-[(N-benzyloxycarbonyl)amino]ethyl 4-azido-4,6-dideoxy-3-O-methyl-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

: 1384442-80-1
2-[(N-benzyloxycarbonyl)amino]ethyl 4-azido-4,6-dideoxy-2-O-methyl-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

: 1384442-83-4
2-[(N-benzyloxycarbonyl)amino]ethyl 4-azido-4,6-dideoxy-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

Guidance literature:: 2-[(N-benzyloxycarbonyl)amino]ethyl 4-azido-3-O-benzoyl-4,6-dideoxy-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside; With silver(l) oxide; In dichloromethane; at 20 ℃; for 1h;

methyl iodide; In dichloromethane; at 20 ℃; for 72h;
DOI:10.1016/j.carres.2012.01.007

Reference yield:

: 1384442-76-5
2-methyl-5-tert-butylphenyl 2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside

: 1384442-83-4
2-[(N-benzyloxycarbonyl)amino]ethyl 4-azido-4,6-dideoxy-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: acetyl chloride / methanol; dichloromethane / 4 h / 20 °C

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

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

4.1: acetyl chloride / methanol; dichloromethane / 144 h / 20 °C

5.1: silver(l) oxide / dichloromethane / 1 h / 20 °C

5.2: 72 h / 20 °C

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; silver trifluoromethanesulfonate; acetyl chloride; silver(l) oxide; In methanol; dichloromethane;
DOI:10.1016/j.carres.2012.01.007

Reference yield:

: 1384442-63-0
2-methyl-5-tert-butylphenyl 1-thio-L-rhamnopyranoside

: 1384442-83-4
2-[(N-benzyloxycarbonyl)amino]ethyl 4-azido-4,6-dideoxy-β-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: camphor-10-sulfonic acid / acetonitrile / 12 h / 20 °C

1.2: 2 h / 0 - 20 °C

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

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

4.1: acetyl chloride / methanol; dichloromethane / 144 h / 20 °C

5.1: silver(l) oxide / dichloromethane / 1 h / 20 °C

5.2: 72 h / 20 °C

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; silver trifluoromethanesulfonate; acetyl chloride; silver(l) oxide; In methanol; dichloromethane; acetonitrile;
DOI:10.1016/j.carres.2012.01.007