(1S,2S,3R,4R)-2-acetamido-4-O-acetyl-3-methylthio-1-O-phenoxythiocarbonyl-1,4-cyclopentanediol

Base Information

Chemical Name:(1S,2S,3R,4R)-2-acetamido-4-O-acetyl-3-methylthio-1-O-phenoxythiocarbonyl-1,4-cyclopentanediol
CAS No.:229306-13-2
Molecular Formula:C₁₇H₂₂N₂O₅S
Molecular Weight:366.438
Hs Code.:

Synonyms:(1S,2S,3R,4R)-2-acetamido-4-O-acetyl-3-methylthio-1-O-phenoxythiocarbonyl-1,4-cyclopentanediol

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Chemical Property of (1S,2S,3R,4R)-2-acetamido-4-O-acetyl-3-methylthio-1-O-phenoxythiocarbonyl-1,4-cyclopentanediol

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Technology Process of (1S,2S,3R,4R)-2-acetamido-4-O-acetyl-3-methylthio-1-O-phenoxythiocarbonyl-1,4-cyclopentanediol

There total 7 articles about (1S,2S,3R,4R)-2-acetamido-4-O-acetyl-3-methylthio-1-O-phenoxythiocarbonyl-1,4-cyclopentanediol 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: 70.0%

: 229306-11-0
(1R,2S,3R,4S,5R)-4-acetamido-1-O-acetyl-2-O-phenoxythiocarbonyl-3-O-phenylcarbamoyl-1,2,3-cyclopentanetriol

: 229306-13-2
(1S,2S,3R,4R)-2-acetamido-4-O-acetyl-3-methylthio-1-O-phenoxythiocarbonyl-1,4-cyclopentanediol

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 2h; Heating;
DOI:10.1016/S0960-894X(99)00224-3

Reference yield:

: 103-71-9
phenyl isocyanate

: 229306-13-2
(1S,2S,3R,4R)-2-acetamido-4-O-acetyl-3-methylthio-1-O-phenoxythiocarbonyl-1,4-cyclopentanediol

Guidance literature:: Multi-step reaction with 6 steps

1: 90 percent / pyridine / 6 h / Ambient temperature

2: 80 percent aq. AcOH / 9 h / 80 °C

3: TsOH / benzene / Ambient temperature

4: 80 percent aq. AcOH / 0.5 h / Ambient temperature

5: DMAP / acetonitrile / 0.5 h / Ambient temperature

6: 70 percent / n-Bu₃SnH, AIBN / toluene / 2 h / Heating

With dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; toluene-4-sulfonic acid; acetic acid; In pyridine; toluene; acetonitrile; benzene;
DOI:10.1016/S0960-894X(99)00224-3

Reference yield:

: 171032-10-3
1,2-O-cyclohexylidene 1D-(1,2,3,4/5)-4-acetamido-5-(methylthio)-1,2,3-cyclopentanetriol

: 229306-13-2
(1S,2S,3R,4R)-2-acetamido-4-O-acetyl-3-methylthio-1-O-phenoxythiocarbonyl-1,4-cyclopentanediol

Guidance literature:: Multi-step reaction with 6 steps

1: 90 percent / pyridine / 6 h / Ambient temperature

2: 80 percent aq. AcOH / 9 h / 80 °C

3: TsOH / benzene / Ambient temperature

4: 80 percent aq. AcOH / 0.5 h / Ambient temperature

5: DMAP / acetonitrile / 0.5 h / Ambient temperature

6: 70 percent / n-Bu₃SnH, AIBN / toluene / 2 h / Heating

With dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; toluene-4-sulfonic acid; acetic acid; In pyridine; toluene; acetonitrile; benzene;
DOI:10.1016/S0960-894X(99)00224-3