Benzoic acid (1S,2R,3S,4R,5R,6R)-2,5-bis-benzyloxycarbonylamino-3,4-dihydroxy-6-methanesulfonyloxy-cyclohexyl ester

Base Information

• Chemical Name: Benzoic acid (1S,2R,3S,4R,5R,6R)-2,5-bis-benzyloxycarbonylamino-3,4-dihydroxy-6-methanesulfonyloxy-cyclohexyl ester
• CAS No.: 95058-19-8
• Molecular Formula: C₃₀H₃₂N₂O₁₁S
• Molecular Weight: 628.657
• Mol file: 95058-19-8.mol

Synonyms:Benzoic acid (1S,2R,3S,4R,5R,6R)-2,5-bis-benzyloxycarbonylamino-3,4-dihydroxy-6-methanesulfonyloxy-cyclohexyl ester

Chemical Property of Benzoic acid (1S,2R,3S,4R,5R,6R)-2,5-bis-benzyloxycarbonylamino-3,4-dihydroxy-6-methanesulfonyloxy-cyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (1S,2R,3S,4R,5R,6R)-2,5-bis-benzyloxycarbonylamino-3,4-dihydroxy-6-methanesulfonyloxy-cyclohexyl ester

There total 4 articles about Benzoic acid (1S,2R,3S,4R,5R,6R)-2,5-bis-benzyloxycarbonylamino-3,4-dihydroxy-6-methanesulfonyloxy-cyclohexyl 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: 93.0%

Benzoic acid (3aR,4S,5R,6S,7S,7aS)-4,7-bis-benzyloxycarbonylamino-6-methanesulfonyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-yl ester (95058-18-7) → Benzoic acid (1S,2R,3S,4R,5R,6R)-2,5-bis-benzyloxycarbonylamino-3,4-dihydroxy-6-methanesulfonyloxy-cyclohexyl ester (95058-19-8)

Guidance literature:

With water; acetic acid; at 80 ℃; for 2h;

DOI:10.1246/cl.1984.1665

Reference yield:

benzoyl chloride (98-88-4) → Benzoic acid (1S,2R,3S,4R,5R,6R)-2,5-bis-benzyloxycarbonylamino-3,4-dihydroxy-6-methanesulfonyloxy-cyclohexyl ester (95058-19-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / pyridine / 21 h / Ambient temperature

2: 70 percent / pyridine

3: 93 percent / AcOH, H₂O / 2 h / 80 °C

With pyridine; water; acetic acid;

DOI:10.1246/cl.1984.1665

Reference yield:

D,L-(1r,2c,3c,4t,5t,6t)-1,4-bis(benzyloxycarbonylamino)-2,3-O-isopropyylidene-2,3,5,6-cyclohexanetetraol (95058-16-5) → Benzoic acid (1S,2R,3S,4R,5R,6R)-2,5-bis-benzyloxycarbonylamino-3,4-dihydroxy-6-methanesulfonyloxy-cyclohexyl ester (95058-19-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / pyridine / 21 h / Ambient temperature

2: 70 percent / pyridine

3: 93 percent / AcOH, H₂O / 2 h / 80 °C

With pyridine; water; acetic acid;

DOI:10.1246/cl.1984.1665

upstream raw materials:

Benzoic acid (3aR,4S,5R,6S,7S,7aS)-4,7-bis-benzyloxycarbonylamino-6-methanesulfonyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-yl ester

benzoyl chloride

D,L-(1r,2c,3c,4t,5t,6t)-1,4-bis(benzyloxycarbonylamino)-2,3-O-isopropyylidene-2,3,5,6-cyclohexanetetraol

Benzoic acid (3aR,4S,5R,6S,7R,7aS)-4,7-bis-benzyloxycarbonylamino-6-hydroxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-yl ester

Downstream raw materials:

Benzoic acid (1R,2R,3S,4R,5S)-2,5-bis-benzyloxycarbonylamino-3-hydroxy-4-trifluoromethanesulfonyloxy-cyclohexyl ester

D,L-(1r,2c,4c,5t,6t)-2,5-bis(benzyloxycarbonylamino)-5-N-methyl-4,6-bis-O-tetrahydropyranyl-1,4,6-cyclohexanetriol

D,L-(1r,2c,4c,5t,6t)-1,4,6-tri-O-acetyl-2,5-bis(benzyloxycarbonylamino)-5-N-methyl-1,4,6-cyclohexanetriol

Acetic acid (1R,2R,3R,5S,6R)-2,5-diacetoxy-3,6-bis-benzyloxycarbonylamino-cyclohexyl ester