3-trifluoroacetamidopropyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: 3-trifluoroacetamidopropyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside
• CAS No.: 334934-29-1
• Molecular Formula: C₂₇H₃₃F₃N₂O₇
• Molecular Weight: 554.563

Synonyms:3-trifluoroacetamidopropyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Chemical Property of 3-trifluoroacetamidopropyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Chemical Property:

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Technology Process of 3-trifluoroacetamidopropyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

There total 4 articles about 3-trifluoroacetamidopropyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-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: 87.0%

3-trifluoroacetamidopropyl 2-acetamido-4,6-O-benzylidene-3-O-benzyl-2-deoxy-β-D-glucopyranoside (334934-28-0) → 3-trifluoroacetamidopropyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside (334934-29-1)

Guidance literature:

With aluminium trichloride; trimethylamine-borane; water; In tetrahydrofuran; at 20 ℃; for 6h;

DOI:10.1016/S0008-6215(01)00002-7

Reference yield: 20.0%

3-trifluoroacetamidopropyl 2-acetamido-4,6-O-benzylidene-3-O-benzyl-2-deoxy-β-D-glucopyranoside (334934-28-0) → 3-trifluoroacetamidopropyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside (334934-29-1) + N-[3-((2R,3R,4R,5S,6R)-3-Acetylamino-4-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-propyl]-2,2,2-trifluoro-acetamide

Guidance literature:

With aluminium trichloride; trimethylamine-borane; water; In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.1016/S0008-6215(03)00015-6

Reference yield:

benzyl bromide (100-39-0) → 3-trifluoroacetamidopropyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside (334934-29-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / NaH / dimethylformamide / 1.5 h / -20 - -15 °C

2: 87 percent / Me₃N*BH₃; AlCl₃; water / tetrahydrofuran / 6 h / 20 °C

With aluminium trichloride; trimethylamine-borane; water; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(01)00002-7

upstream raw materials:

3-trifluoroacetamidopropyl 2-acetamido-4,6-O-benzylidene-3-O-benzyl-2-deoxy-β-D-glucopyranoside

benzyl bromide

Downstream raw materials:

3-trifluoroacetamidopropyl (2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Benzoic acid (2S,4aR,6S,7R,8S,8aS)-7-acetoxy-6-{(2R,3S,4R,5R,6R)-5-acetylamino-4-benzyloxy-2-benzyloxymethyl-6-[3-(2,2,2-trifluoro-acetylamino)-propoxy]-tetrahydro-pyran-3-yloxy}-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

Benzoic acid (2S,4aR,6S,7R,8R,8aS)-6-{(2R,3S,4R,5R,6R)-5-acetylamino-4-benzyloxy-2-benzyloxymethyl-6-[3-(2,2,2-trifluoro-acetylamino)-propoxy]-tetrahydro-pyran-3-yloxy}-7-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

3-trifluoroacetamidopropyl (2-O-acetyl-3-O-benzoyl-β-D-galactopyranosyl-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

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