(allyl 2,3,4-tri-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetimidate

Base Information

Chemical Name:(allyl 2,3,4-tri-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetimidate
CAS No.:1379585-64-4
Molecular Formula:C₄₇H₄₉Cl₃N₄O₁₂
Molecular Weight:968.285
Hs Code.:

Synonyms:(allyl 2,3,4-tri-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetimidate

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Chemical Property of (allyl 2,3,4-tri-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetimidate

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Technology Process of (allyl 2,3,4-tri-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetimidate

There total 2 articles about (allyl 2,3,4-tri-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetimidate 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: 87.0%

: (allyl 2,3,4-tri-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-D-glucopyranose

: 545-06-2
trichloroacetonitrile

: 1379585-64-4
(allyl 2,3,4-tri-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetimidate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 2h; Inert atmosphere;
DOI:10.1016/j.carres.2012.03.014

Reference yield:

: 1379585-62-2
(allyl 2,3,4-tri-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-1,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-D-glucopyranose

: 1379585-64-4
(allyl 2,3,4-tri-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 2 steps

1: hydrazinium monoacetate / N,N-dimethyl-formamide / 1 h / 50 °C / Inert atmosphere

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 2 h / 0 °C / Inert atmosphere

With hydrazinium monoacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.carres.2012.03.014

Reference yield: 43.0%

: 1379585-66-6
(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-O-(1→4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose

: 1379585-64-4
(allyl 2,3,4-tri-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetimidate

: 1379585-68-8
(allyl 2,3,4-tri-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose

: 1379585-67-7
(allyl 2,3,4-tri-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1->4)-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose

Guidance literature:: (methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-O-(1→4)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose; (allyl 2,3,4-tri-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetimidate; In toluene; at 20 ℃; for 0.5h; Inert atmosphere; Molecular sieve;

With t-butyldimethylsiyl triflate; In dichloromethane; toluene; at -20 - 20 ℃; for 7h; diastereoselective reaction; Inert atmosphere;
DOI:10.1016/j.carres.2012.03.014