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

Base Information

• Chemical Name: (1R,2R,3R,4S,5R)-4-acetamido-2-O-acetyl-1-O-phenoxythiocarbonyl-3-O-phenylcarbamoyl-1,2,3-cyclopentanetriol
• CAS No.: 229306-12-1
• Molecular Formula: C₂₄H₂₆N₂O₇S₂
• Molecular Weight: 518.612
• Mol file: 229306-12-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about (1R,2R,3R,4S,5R)-4-acetamido-2-O-acetyl-1-O-phenoxythiocarbonyl-3-O-phenylcarbamoyl-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: 65.0%

phenylcarbonochloridothioate (1005-56-7) + 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) → (1R,2S,3R,4S,5R)-4-acetamido-1-O-acetyl-2-O-phenoxythiocarbonyl-3-O-phenylcarbamoyl-1,2,3-cyclopentanetriol (229306-11-0) + (1R,2R,3R,4S,5R)-4-acetamido-2-O-acetyl-1-O-phenoxythiocarbonyl-3-O-phenylcarbamoyl-1,2,3-cyclopentanetriol (229306-12-1)

Guidance literature:

Phenyl-carbamic acid (3aR,4R,5S,6R,6aR)-5-acetylamino-2-methoxy-2-methyl-6-methylsulfanyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl ester; In water; acetic acid; at 20 ℃; for 0.5h;

phenylcarbonochloridothioate; With dmap; In acetonitrile; at 20 ℃; for 0.5h; Further stages.;

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

Reference yield:

phenyl isocyanate (103-71-9) → (1R,2R,3R,4S,5R)-4-acetamido-2-O-acetyl-1-O-phenoxythiocarbonyl-3-O-phenylcarbamoyl-1,2,3-cyclopentanetriol (229306-12-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 90 percent / pyridine / 6 h / 20 °C

2.1: H₂O; acetic acid / 9 h / 80 °C

3.1: TsOH / benzene / 3 h / 20 °C

4.1: H₂O; acetic acid / 0.5 h / 20 °C

4.2: 16 percent / DMAP / acetonitrile / 0.5 h / 20 °C

With toluene-4-sulfonic acid; In pyridine; water; acetic acid; benzene; 1.1: Acylation / 2.1: Hydrolysis / 3.1: Cyclization / 4.1: Hydrolysis / 4.2: Acylation;

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

Reference yield:

1,2-O-cyclohexylidene 1D-(1,2,3,4/5)-4-acetamido-5-(methylthio)-1,2,3-cyclopentanetriol (171032-10-3) → (1R,2R,3R,4S,5R)-4-acetamido-2-O-acetyl-1-O-phenoxythiocarbonyl-3-O-phenylcarbamoyl-1,2,3-cyclopentanetriol (229306-12-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 90 percent / pyridine / 6 h / 20 °C

2.1: H₂O; acetic acid / 9 h / 80 °C

3.1: TsOH / benzene / 3 h / 20 °C

4.1: H₂O; acetic acid / 0.5 h / 20 °C

4.2: 16 percent / DMAP / acetonitrile / 0.5 h / 20 °C

With toluene-4-sulfonic acid; In pyridine; water; acetic acid; benzene; 1.1: Acylation / 2.1: Hydrolysis / 3.1: Cyclization / 4.1: Hydrolysis / 4.2: Acylation;

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

upstream raw materials:

phenylcarbonochloridothioate

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

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

phenyl isocyanate