Benzoic acid (3R,4R,5R,6S)-5-amino-6-((3R,4R,5R,6S)-5-amino-4-benzyloxy-6-methoxy-tetrahydro-pyran-3-yloxy)-4-methanesulfonyloxy-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Benzoic acid (3R,4R,5R,6S)-5-amino-6-((3R,4R,5R,6S)-5-amino-4-benzyloxy-6-methoxy-tetrahydro-pyran-3-yloxy)-4-methanesulfonyloxy-tetrahydro-pyran-3-yl ester
• CAS No.: 83030-03-9
• Molecular Formula: C₂₆H₃₄N₂O₁₀S
• Molecular Weight: 566.629

Synonyms:Benzoic acid (3R,4R,5R,6S)-5-amino-6-((3R,4R,5R,6S)-5-amino-4-benzyloxy-6-methoxy-tetrahydro-pyran-3-yloxy)-4-methanesulfonyloxy-tetrahydro-pyran-3-yl ester

Chemical Property of Benzoic acid (3R,4R,5R,6S)-5-amino-6-((3R,4R,5R,6S)-5-amino-4-benzyloxy-6-methoxy-tetrahydro-pyran-3-yloxy)-4-methanesulfonyloxy-tetrahydro-pyran-3-yl ester

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Technology Process of Benzoic acid (3R,4R,5R,6S)-5-amino-6-((3R,4R,5R,6S)-5-amino-4-benzyloxy-6-methoxy-tetrahydro-pyran-3-yloxy)-4-methanesulfonyloxy-tetrahydro-pyran-3-yl ester

There total 14 articles about Benzoic acid (3R,4R,5R,6S)-5-amino-6-((3R,4R,5R,6S)-5-amino-4-benzyloxy-6-methoxy-tetrahydro-pyran-3-yloxy)-4-methanesulfonyloxy-tetrahydro-pyran-3-yl 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:

methyl 2-azido-3-O-benzyl-2-deoxy-α-D-xylopyranoside (83030-01-7) → Benzoic acid (3R,4R,5R,6S)-5-amino-6-((3R,4R,5R,6S)-5-amino-4-benzyloxy-6-methoxy-tetrahydro-pyran-3-yloxy)-4-methanesulfonyloxy-tetrahydro-pyran-3-yl ester (83030-03-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) silver perchlorate, 2,4,6-trimethylpyridine, Drierite / 1.) nitromethane, -10 degC, 1 h; 2.) nitromethane, -10 degC, 60 h

2: sodium methoxide / methanol

3: 61 percent / triethylamine / acetone / 18 h / Ambient temperature

4: 97 percent / pyridine

5: hydrogen / platinum oxide / CH₂Cl₂

With 2,4,6-trimethyl-pyridine; calcium sulfate; hydrogen; sodium methylate; silver perchlorate; triethylamine; platinum(IV) oxide; In pyridine; methanol; dichloromethane; acetone;

DOI:10.1246/bcsj.59.3137

Reference yield:

methyl 2-azido-4-O-(2-azido-4-O-benzoyl-2-deoxy-3-O-methylsulfonyl-β-D-xylopyranosyl)-3-O-benzoyl-2-deoxy-α-D-xylopyranoside (83030-02-8) → Benzoic acid (3R,4R,5R,6S)-5-amino-6-((3R,4R,5R,6S)-5-amino-4-benzyloxy-6-methoxy-tetrahydro-pyran-3-yloxy)-4-methanesulfonyloxy-tetrahydro-pyran-3-yl ester (83030-03-9)

Guidance literature:

With hydrogen; platinum(IV) oxide;

DOI:10.1016/S0040-4039(00)87195-6

Reference yield:

methyl 2-azido-4-O-(2-azido-2-deoxy-β-D-xylopyranosyl)-3-O-benzyl-2-deoxy-α-D-xylopyranoside (109200-42-2) → Benzoic acid (3R,4R,5R,6S)-5-amino-6-((3R,4R,5R,6S)-5-amino-4-benzyloxy-6-methoxy-tetrahydro-pyran-3-yloxy)-4-methanesulfonyloxy-tetrahydro-pyran-3-yl ester (83030-03-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 61 percent / triethylamine / acetone / 18 h / Ambient temperature

2: 97 percent / pyridine

3: hydrogen / platinum oxide / CH₂Cl₂

With hydrogen; triethylamine; platinum(IV) oxide; In pyridine; dichloromethane; acetone;

DOI:10.1246/bcsj.59.3137

upstream raw materials:

methyl 2-azido-4-O-(2-azido-4-O-benzoyl-2-deoxy-3-O-methylsulfonyl-β-D-xylopyranosyl)-3-O-benzoyl-2-deoxy-α-D-xylopyranoside

methyl 2-azido-3-O-benzyl-2-deoxy-α-D-xylopyranoside

3,4-di-O-acetyl-2-azido-2-deoxy-α-D-xylopyranosyl chloride

methyl 2-azido-4-O-(2-azido-2-deoxy-β-D-xylopyranosyl)-3-O-benzyl-2-deoxy-α-D-xylopyranoside

Downstream raw materials:

methyl 2-amino-4-O-(4-O-benzoyl-2,3-dideoxy-2,3-epimino-β-D-ribopyranosyl)-3-O-benzyl-α-D-xylopyranoside

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