1,2-O-cyclohexylidene (1R,2S,3R,4S,5R)-4-acetamido-3-O-phenylcarbamoyl-5-methylthio-1,2,3-cyclopentanetriol

Base Information

• Chemical Name: 1,2-O-cyclohexylidene (1R,2S,3R,4S,5R)-4-acetamido-3-O-phenylcarbamoyl-5-methylthio-1,2,3-cyclopentanetriol
• CAS No.: 229306-07-4
• Molecular Formula: C₂₁H₂₈N₂O₅S
• Molecular Weight: 420.53
• Mol file: 229306-07-4.mol

Synonyms:1,2-O-cyclohexylidene (1R,2S,3R,4S,5R)-4-acetamido-3-O-phenylcarbamoyl-5-methylthio-1,2,3-cyclopentanetriol

Chemical Property of 1,2-O-cyclohexylidene (1R,2S,3R,4S,5R)-4-acetamido-3-O-phenylcarbamoyl-5-methylthio-1,2,3-cyclopentanetriol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2-O-cyclohexylidene (1R,2S,3R,4S,5R)-4-acetamido-3-O-phenylcarbamoyl-5-methylthio-1,2,3-cyclopentanetriol

There total 1 articles about 1,2-O-cyclohexylidene (1R,2S,3R,4S,5R)-4-acetamido-3-O-phenylcarbamoyl-5-methylthio-1,2,3-cyclopentanetriol 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: 90.0%

phenyl isocyanate (103-71-9) + 1,2-O-cyclohexylidene 1D-(1,2,3,4/5)-4-acetamido-5-(methylthio)-1,2,3-cyclopentanetriol (171032-10-3) → 1,2-O-cyclohexylidene (1R,2S,3R,4S,5R)-4-acetamido-3-O-phenylcarbamoyl-5-methylthio-1,2,3-cyclopentanetriol (229306-07-4)

Guidance literature:

In pyridine; for 6h; Ambient temperature;

DOI:10.1016/S0960-894X(99)00224-3

Reference yield:

1,2-O-cyclohexylidene (1R,2S,3R,4S,5R)-4-acetamido-3-O-phenylcarbamoyl-5-methylthio-1,2,3-cyclopentanetriol (229306-07-4) → Phenyl-carbamic acid (1R,2S,3R,4R,5S)-2-acetylamino-4,5-dihydroxy-3-methylsulfanyl-cyclopentyl ester

Guidance literature:

With acetic acid; at 80 ℃; for 9h;

DOI:10.1016/S0960-894X(99)00224-3

Reference yield:

1,2-O-cyclohexylidene (1R,2S,3R,4S,5R)-4-acetamido-3-O-phenylcarbamoyl-5-methylthio-1,2,3-cyclopentanetriol (229306-07-4) → Phenyl-carbamic acid (3aR,4R,5S,6R,6aR)-5-acetylamino-2-methoxy-2-methyl-6-methylsulfanyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl ester (229306-08-5)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂O; acetic acid / 9 h / 80 °C

2: TsOH / benzene / 3 h / 20 °C

With toluene-4-sulfonic acid; In water; acetic acid; benzene; 1: Hydrolysis / 2: Cyclization;

DOI:10.1002/(SICI)1099-0690(200005)2000:9<1759::AID-EJOC1759>3.0.CO;2-J

upstream raw materials:

phenyl isocyanate

1,2-O-cyclohexylidene 1D-(1,2,3,4/5)-4-acetamido-5-(methylthio)-1,2,3-cyclopentanetriol

Downstream raw materials:

Phenyl-carbamic acid (3aR,4R,5S,6R,6aR)-5-acetylamino-2-methoxy-2-methyl-6-methylsulfanyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl ester

(1R,2S,3R,4S,5R)-4-acetamido-2-O-acetyl-3-O-phenylcarbamoyl-1,2,3-cyclopentanetriol

(1R,2S,3R,4S,5R)-4-acetamido-1-O-acetyl-3-O-phenylcarbamoyl-1,2,3-cyclopentanetriol

(1R,2R,3R,4S,5R)-4-acetamido-2-O-acetyl-1-O-phenoxythiocarbonyl-3-O-phenylcarbamoyl-1,2,3-cyclopentanetriol