Benzoic acid (3S,4S,5S,6R)-4,6-diacetoxy-3-acetylamino-5-benzyloxy-cyclohex-1-enylmethyl ester

Base Information

• Chemical Name: Benzoic acid (3S,4S,5S,6R)-4,6-diacetoxy-3-acetylamino-5-benzyloxy-cyclohex-1-enylmethyl ester
• CAS No.: 119951-79-0
• Molecular Formula: C₂₇H₂₉NO₈
• Molecular Weight: 495.529
• Mol file: 119951-79-0.mol

Synonyms:Benzoic acid (3S,4S,5S,6R)-4,6-diacetoxy-3-acetylamino-5-benzyloxy-cyclohex-1-enylmethyl ester

Chemical Property of Benzoic acid (3S,4S,5S,6R)-4,6-diacetoxy-3-acetylamino-5-benzyloxy-cyclohex-1-enylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (3S,4S,5S,6R)-4,6-diacetoxy-3-acetylamino-5-benzyloxy-cyclohex-1-enylmethyl ester

There total 3 articles about Benzoic acid (3S,4S,5S,6R)-4,6-diacetoxy-3-acetylamino-5-benzyloxy-cyclohex-1-enylmethyl 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: 89.0%

Benzoic acid (1R,2S,3R,4S,5S)-2,4-diacetoxy-5-acetylamino-3-benzyloxy-1-hydroxy-cyclohexylmethyl ester (119951-78-9) → Benzoic acid (3S,4S,5S,6R)-4,6-diacetoxy-3-acetylamino-5-benzyloxy-cyclohex-1-enylmethyl ester (119951-79-0)

Guidance literature:

With thionyl chloride; In pyridine; at 2 ℃; for 0.25h;

Reference yield:

Benzoic acid (1R,2S,3R,4S,5S)-2,4-diacetoxy-5-acetylamino-3-benzyloxy-1-hydroxy-6-nitro-cyclohexylmethyl ester (119951-77-8,120053-41-0) → Benzoic acid (3S,4S,5S,6R)-4,6-diacetoxy-3-acetylamino-5-benzyloxy-cyclohex-1-enylmethyl ester (119951-79-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / n-Bu3SnH, α-α'azobis-iso-butyronitrile / benzene

2: 89 percent / SOCl₂ / pyridine / 0.25 h / 2 °C

With thionyl chloride; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In pyridine; benzene;

Reference yield:

Benzoic acid (1R,2S,3R,4S,5R,6R)-2,4,5-triacetoxy-3-benzyloxy-1-hydroxy-6-nitro-cyclohexylmethyl ester (119951-76-7) → Benzoic acid (3S,4S,5S,6R)-4,6-diacetoxy-3-acetylamino-5-benzyloxy-cyclohex-1-enylmethyl ester (119951-79-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) liq. NH₃; 2.) p-TsOH*H₂O / 1.) THF, -78 deg C, 2 h

2: 60 percent / n-Bu3SnH, α-α'azobis-iso-butyronitrile / benzene

3: 89 percent / SOCl₂ / pyridine / 0.25 h / 2 °C

With thionyl chloride; 2,2'-azobis(isobutyronitrile); ammonia; tri-n-butyl-tin hydride; toluene-4-sulfonic acid; In pyridine; benzene;

upstream raw materials:

Benzoic acid (1R,2S,3R,4S,5S)-2,4-diacetoxy-5-acetylamino-3-benzyloxy-1-hydroxy-cyclohexylmethyl ester

Benzoic acid (1R,2S,3R,4S,5S)-2,4-diacetoxy-5-acetylamino-3-benzyloxy-1-hydroxy-6-nitro-cyclohexylmethyl ester

Benzoic acid (1R,2S,3R,4S,5R,6R)-2,4,5-triacetoxy-3-benzyloxy-1-hydroxy-6-nitro-cyclohexylmethyl ester

Downstream raw materials:

(1L)-(1,3,4/2)-4-acetamido-1,2,3-tri-O-acetyl-4-[(acetoxy)methyl]cyclohex-5-ene-1,2,3-triol

valienamine

N-((1S,4R,5S,6S)-4,5,6-Trihydroxy-3-hydroxymethyl-cyclohex-2-enyl)-acetamide