5-(methoxycarbonyl)pentyl (4,6-di-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-stearoyl-α-L-rhamnopyranoside

Base Information

Chemical Name:5-(methoxycarbonyl)pentyl (4,6-di-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-stearoyl-α-L-rhamnopyranoside
CAS No.:270075-76-8
Molecular Formula:C₅₀H₇₆ClN₃O₁₆
Molecular Weight:1010.62
Hs Code.:

5-(methoxycarbonyl)pentyl (4,6-di-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-stearoyl-α-L-rhamnopyranoside

Synonyms:5-(methoxycarbonyl)pentyl (4,6-di-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-stearoyl-α-L-rhamnopyranoside

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Chemical Property of 5-(methoxycarbonyl)pentyl (4,6-di-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-stearoyl-α-L-rhamnopyranoside

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Technology Process of 5-(methoxycarbonyl)pentyl (4,6-di-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-stearoyl-α-L-rhamnopyranoside

There total 18 articles about 5-(methoxycarbonyl)pentyl (4,6-di-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-stearoyl-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:

: Benzoic acid (2R,3R,4R,5S,6S)-4-[(2R,3R,4R,5S,6R)-3-azido-4-(2-chloro-acetoxy)-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy]-2-(5-methoxycarbonyl-pentyloxy)-6-methyl-5-octadecanoyloxy-tetrahydro-pyran-3-yl ester

: 108-24-7
acetic anhydride

: 270075-76-8
5-(methoxycarbonyl)pentyl (4,6-di-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-stearoyl-α-L-rhamnopyranoside

Guidance literature:: With dmap; In pyridine; at 22 ℃; for 0.333333h;
DOI:10.1016/j.carres.2006.04.006

Reference yield:

: Chloro-acetic acid (2R,3S,4R,5R)-3-acetoxy-2-acetoxymethyl-5-azido-6-bromo-tetrahydro-pyran-4-yl ester

: 270075-71-3
5-(methoxycarbonyl)pentyl 2-O-benzoyl-4-O-stearoyl-α-L-rhamnopyranoside

: 270075-76-8
5-(methoxycarbonyl)pentyl (4,6-di-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-stearoyl-α-L-rhamnopyranoside

Guidance literature:: With 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 0.333333h;
DOI:10.1016/S0957-4166(99)00553-4

Reference yield:

: 904690-67-1
phenyl 2-azido-2-deoxy-4,6-O-diphenylmethylidene-1-thio-β-D-glucopyranoside

: 270075-76-8
5-(methoxycarbonyl)pentyl (4,6-di-O-acetyl-2-azido-3-O-chloroacetyl-2-deoxy-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-stearoyl-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 96 percent / 2,4,6-tri-tert-butylpyrimidine / CH₂Cl₂ / 1 h / 0 °C

2: 89 percent / N-iodosuccinimide; TMSOTf / CH₂Cl₂ / 1 h / 0 - 22 °C

3: trifluoroacetic acid; aq. HCl / 0.25 h / 22 °C

4: 6.4 g / 4-dimethylaminopyridine / pyridine / 0.33 h / 22 °C

With hydrogenchloride; dmap; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; trifluoroacetic acid; 2,4,6-tri-tert-butylpyrimidine; In pyridine; dichloromethane;
DOI:10.1016/j.carres.2006.04.006