6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranosyl trichloroacetimidate

Base Information

• Chemical Name: 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranosyl trichloroacetimidate
• CAS No.: 133076-40-1
• Molecular Formula: C₂₄H₂₅Cl₃N₄O₆
• Molecular Weight: 571.845

Synonyms:6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranosyl trichloroacetimidate

Chemical Property of 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranosyl trichloroacetimidate

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Technology Process of 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranosyl trichloroacetimidate

There total 14 articles about 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-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: 68.0%

trichloroacetonitrile (545-06-2) + 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α/β-D-glucopyranose → 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranosyl trichloroacetimidate (133076-40-1)

Guidance literature:

With potassium carbonate; In dichloromethane; for 7h; Ambient temperature;

DOI:10.1016/S0008-6215(98)00045-7

Reference yield: 58.0%

trichloroacetonitrile (545-06-2) + 6-O-Acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranose (157896-03-2) → 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranosyl trichloroacetimidate (133076-40-1) + 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl trichloroacetimidate (154970-28-2)

Guidance literature:

With potassium carbonate; In dichloromethane; for 20h;

DOI:10.1016/S0040-4020(99)00526-8

Reference yield: 53.0%

trichloroacetonitrile (545-06-2) + 6-O-Acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranose (157896-03-2) → 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranosyl trichloroacetimidate (133076-40-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere; Industry scale;

upstream raw materials:

1,6-di-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α,β-D-glucopyranose

trichloroacetonitrile

6-O-Acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranose

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose

Downstream raw materials:

1-(6-O-Acetyl-2-azido-2-deoxy-3,4-dibenzyl-α-D-glucopyranosyl)-6-O-allyl-2,3,4,5-tetra-O-benzyl-D-chiro-inositol

2-O-Allyl-3,4,5-tri-O-benzyl-1-O-(dibenzylphosphono)-6-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol

Acetic acid (2R,3S,4R,5R,6R)-5-azido-3,4-bis-benzyloxy-6-((2R,3R,4S,5R,6S)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-yloxy)-tetrahydro-pyran-2-ylmethyl ester

methyl 3,4,6-tri-O-benzyl-2-deoxy-2-isothiocyanato-α-D-glucopyranosyl-(1->3)-2,4,6-tri-O-benzyl-α-D-glucopyranoside

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