benzyl 2-acetamido-6-O-benzoyl-2-deoxy-4-O-mesyl-3-O--α-D-glucopyranoside

Base Information

• Chemical Name: benzyl 2-acetamido-6-O-benzoyl-2-deoxy-4-O-mesyl-3-O--α-D-glucopyranoside
• CAS No.: 83055-33-8
• Molecular Formula: C₂₇H₃₃NO₁₁S
• Molecular Weight: 579.625

Synonyms:benzyl 2-acetamido-6-O-benzoyl-2-deoxy-4-O-mesyl-3-O--α-D-glucopyranoside

Chemical Property of benzyl 2-acetamido-6-O-benzoyl-2-deoxy-4-O-mesyl-3-O--α-D-glucopyranoside

Chemical Property:

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Technology Process of benzyl 2-acetamido-6-O-benzoyl-2-deoxy-4-O-mesyl-3-O--α-D-glucopyranoside

There total 1 articles about benzyl 2-acetamido-6-O-benzoyl-2-deoxy-4-O-mesyl-3-O--α-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: 93.0%

methanesulfonyl chloride (124-63-0) + benzyl 2-acetamido-6-O-benzoyl-2-deoxy-3-O--α-D-glucopyranoside (69323-71-3) → benzyl 2-acetamido-6-O-benzoyl-2-deoxy-4-O-mesyl-3-O--α-D-glucopyranoside (83055-33-8)

Guidance literature:

With pyridine; at 20 ℃; for 2h;

DOI:10.1016/S0008-6215(00)80688-6

Reference yield: 34.0%

benzyl 2-acetamido-6-O-benzoyl-2-deoxy-4-O-mesyl-3-O--α-D-glucopyranoside (83055-33-8) → benzyl 2-acetamido-4-azido-6-O-benzoyl-2,4-dideoxy-3-O--α-D-galactopyranoside (83055-37-2)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 100 ℃; for 8h; Heating;

DOI:10.1016/S0008-6215(00)80688-6

Reference yield:

benzyl 2-acetamido-6-O-benzoyl-2-deoxy-4-O-mesyl-3-O--α-D-glucopyranoside (83055-33-8) → benzyl 2-acetamido-4-azido-2,4-dideoxy-3-O--α-D-galactopyranoside (83055-38-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 34 percent / sodium azide / dimethylformamide / 8 h / 100 °C / Heating

2: 91 percent / 1.) methanol; 2.) Amberlite IR-120 (H⁺) resin / 1.) sodium methoxide / 0.5 h / Ambient temperature

With methanol; sodium azide; Amberlite IR-120 (H⁺) resin; sodium methylate; In N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)80688-6

upstream raw materials:

methanesulfonyl chloride

benzyl 2-acetamido-6-O-benzoyl-2-deoxy-3-O--α-D-glucopyranoside

Downstream raw materials:

benzyl 2-acetamido-4-azido-6-O-benzoyl-2,4-dideoxy-3-O--α-D-galactopyranoside

benzyl 2-acetamido-4-azido-2,4-dideoxy-3-O--α-D-galactopyranoside

(R)-2-((2S,3R,4R,5R,6S)-3-Acetylamino-5-azido-2-benzyloxy-6-methanesulfonyloxymethyl-tetrahydro-pyran-4-yloxy)-propionic acid

Benzoic acid (2S,3R,4R,5R,6S)-5-acetylamino-3-azido-6-benzyloxy-4-((R)-1-carboxy-ethoxy)-tetrahydro-pyran-2-ylmethyl ester

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