Benzoic acid (2R,3S,4R,5R,6S)-5-acetylamino-6-benzyloxy-4-methoxy-3-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester

Base Information

• Chemical Name: Benzoic acid (2R,3S,4R,5R,6S)-5-acetylamino-6-benzyloxy-4-methoxy-3-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester
• CAS No.: 93215-46-4
• Molecular Formula: C₃₇H₄₅NO₁₆
• Molecular Weight: 759.761

Synonyms:

Chemical Property of Benzoic acid (2R,3S,4R,5R,6S)-5-acetylamino-6-benzyloxy-4-methoxy-3-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of Benzoic acid (2R,3S,4R,5R,6S)-5-acetylamino-6-benzyloxy-4-methoxy-3-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester

There total 5 articles about Benzoic acid (2R,3S,4R,5R,6S)-5-acetylamino-6-benzyloxy-4-methoxy-3-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester 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:

benzoyl chloride (98-88-4) → Benzoic acid (2R,3S,4R,5R,6S)-5-acetylamino-6-benzyloxy-4-methoxy-3-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester (93215-46-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / triethylamine / CH₂Cl₂ / 3 h / -40 °C

2: 1,1,3,3-tetramethylurea, silver trifluoromethansulfonate / CH₂Cl₂ / 48 h / Ambient temperature

With silver trifluoromethanesulfonate; triethylamine; tetramethylurea; In dichloromethane;

DOI:10.1016/0008-6215(84)85069-7

Reference yield:

benzyl 4,6-O-benzylidene-2-acetylamino-2-deoxy-α-D-glucopyranoside (13343-63-0) → Benzoic acid (2R,3S,4R,5R,6S)-5-acetylamino-6-benzyloxy-4-methoxy-3-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester (93215-46-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 52 percent / silver oxide / dimethylformamide / 6 h / Ambient temperature

2: 90 percent / 60 percent aq. acetic acid / 1 h / 100 °C

3: 71 percent / triethylamine / CH₂Cl₂ / 3 h / -40 °C

4: 1,1,3,3-tetramethylurea, silver trifluoromethansulfonate / CH₂Cl₂ / 48 h / Ambient temperature

With silver trifluoromethanesulfonate; acetic acid; triethylamine; tetramethylurea; silver(l) oxide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(84)85069-7

Reference yield:

benzyl 2-acetamido-2-deoxy-3-O-methyl-α-D-glucopyranoside (93215-41-9) → Benzoic acid (2R,3S,4R,5R,6S)-5-acetylamino-6-benzyloxy-4-methoxy-3-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylmethyl ester (93215-46-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / triethylamine / CH₂Cl₂ / 3 h / -40 °C

2: 1,1,3,3-tetramethylurea, silver trifluoromethansulfonate / CH₂Cl₂ / 48 h / Ambient temperature

With silver trifluoromethanesulfonate; triethylamine; tetramethylurea; In dichloromethane;

DOI:10.1016/0008-6215(84)85069-7

upstream raw materials:

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

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

benzoyl chloride

benzyl 4,6-O-benzylidene-2-acetylamino-2-deoxy-α-D-glucopyranoside

Downstream raw materials:

benzyl 2-acetamido-2-deoxy-4-O-β-D-galactopyranosyl-3-O-methyl-α-D-glucopyranoside

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