1,6-anhydro-4-O-[3'-O-benzyl-4',6'-O-benzylidene-2'-deoxy-2'-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-3-O-[(R)-1-(ethoxycarbonyl)ethyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranoside

Base Information

• Chemical Name: 1,6-anhydro-4-O-[3'-O-benzyl-4',6'-O-benzylidene-2'-deoxy-2'-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-3-O-[(R)-1-(ethoxycarbonyl)ethyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranoside
• CAS No.: 1104583-62-1
• Molecular Formula: C₃₇H₄₂Cl₆N₂O₁₄
• Molecular Weight: 951.463

Synonyms:1,6-anhydro-4-O-[3'-O-benzyl-4',6'-O-benzylidene-2'-deoxy-2'-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-3-O-[(R)-1-(ethoxycarbonyl)ethyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranoside

Chemical Property of 1,6-anhydro-4-O-[3'-O-benzyl-4',6'-O-benzylidene-2'-deoxy-2'-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-3-O-[(R)-1-(ethoxycarbonyl)ethyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranoside

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Technology Process of 1,6-anhydro-4-O-[3'-O-benzyl-4',6'-O-benzylidene-2'-deoxy-2'-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-3-O-[(R)-1-(ethoxycarbonyl)ethyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranoside

There total 1 articles about 1,6-anhydro-4-O-[3'-O-benzyl-4',6'-O-benzylidene-2'-deoxy-2'-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-3-O-[(R)-1-(ethoxycarbonyl)ethyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranoside 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: 65.0%

2-trichloroethoxycarbonylamino-1,6-anhydro-2-deoxy-4-O-[(1R)-1-(ethyoxycarbonyl)ethyl]-β-D-glucopyranose + 2,2,2-Trichloro-acetimidic acid (2R,4aR,7R,8R,8aS)-8-benzyloxy-2-phenyl-7-(2,2,2-trichloro-ethoxycarbonylamino)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl ester (391860-83-6) → 1,6-anhydro-4-O-[3'-O-benzyl-4',6'-O-benzylidene-2'-deoxy-2'-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-3-O-[(R)-1-(ethoxycarbonyl)ethyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranoside (1104583-62-1)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -17 ℃; for 0.5h; Molecular sieve; Inert atmosphere;

DOI:10.1002/chem.200801121

Reference yield: 81.0%

1,6-anhydro-4-O-[3'-O-benzyl-4',6'-O-benzylidene-2'-deoxy-2'-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-3-O-[(R)-1-(ethoxycarbonyl)ethyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranoside (1104583-62-1) + acetic anhydride (108-24-7) → 1,6-anhydro-4-O-(3'-O-benzyl-4',6'-O-benzylidene-2'-deoxy-2'-acetylamino-β-D-glucopyranosyl)-3-O-[(R)-1-(ethoxycarbonyl)ethyl-2-deoxy-2-acetylamino]-D-glucopyranoside (1104583-64-3)

Guidance literature:

With zinc/copper couple; acetic acid; In tetrahydrofuran; for 1h;

DOI:10.1002/chem.200801121

Reference yield:

1,6-anhydro-4-O-[3'-O-benzyl-4',6'-O-benzylidene-2'-deoxy-2'-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-3-O-[(R)-1-(ethoxycarbonyl)ethyl]-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranoside (1104583-62-1) → 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-1,6-anhydro-2-deoxy-3-O-[(1R)-1-carboxyethyl]-β-D-glucopyranose (1104583-66-5)

Guidance literature:

Multi-step reaction with 2 steps

1: copper; acetic acid; zinc / tetrahydrofuran

2: water; lithium hydroxide / tetrahydrofuran; 1,4-dioxane

With water; copper; acetic acid; lithium hydroxide; zinc; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1016/S0076-6879(10)78016-2

upstream raw materials:

2,2,2-Trichloro-acetimidic acid (2R,4aR,7R,8R,8aS)-8-benzyloxy-2-phenyl-7-(2,2,2-trichloro-ethoxycarbonylamino)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl ester

Downstream raw materials:

1,6-anhydro-4-O-(3'-O-benzyl-4',6'-O-benzylidene-2'-deoxy-2'-acetylamino-β-D-glucopyranosyl)-3-O-[(R)-1-(ethoxycarbonyl)ethyl-2-deoxy-2-acetylamino]-D-glucopyranoside

2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-1,6-anhydro-2-deoxy-3-O-[(1R)-1-carboxyethyl]-β-D-glucopyranose

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