1,2-O-cyclohexylidene (1S,2R,3S,4R)-3-acetamido-4-O-[(2S)-2-O-acetylmandelyl]-1,2,4-cyclopentanetetrol

Base Information

Chemical Name:1,2-O-cyclohexylidene (1S,2R,3S,4R)-3-acetamido-4-O-[(2S)-2-O-acetylmandelyl]-1,2,4-cyclopentanetetrol
CAS No.:229306-17-6
Molecular Formula:C₂₃H₂₉NO₇
Molecular Weight:431.486
Hs Code.:

Synonyms:1,2-O-cyclohexylidene (1S,2R,3S,4R)-3-acetamido-4-O-[(2S)-2-O-acetylmandelyl]-1,2,4-cyclopentanetetrol

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Chemical Property of 1,2-O-cyclohexylidene (1S,2R,3S,4R)-3-acetamido-4-O-[(2S)-2-O-acetylmandelyl]-1,2,4-cyclopentanetetrol

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Technology Process of 1,2-O-cyclohexylidene (1S,2R,3S,4R)-3-acetamido-4-O-[(2S)-2-O-acetylmandelyl]-1,2,4-cyclopentanetetrol

There total 5 articles about 1,2-O-cyclohexylidene (1S,2R,3S,4R)-3-acetamido-4-O-[(2S)-2-O-acetylmandelyl]-1,2,4-cyclopentanetetrol 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: 77.0%

: 229306-16-5
1,2-O-cyclohexylidene (1R,2R,3R,4S,5S)-5-acetamido-4-O-[(2S)-2-O-acetylmandelyl]-3-O-phenoxythiocarbonyl-1,2,3,4-cyclopentanetetrol

: 229306-17-6
1,2-O-cyclohexylidene (1S,2R,3S,4R)-3-acetamido-4-O-[(2S)-2-O-acetylmandelyl]-1,2,4-cyclopentanetetrol

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 0.5h; Heating;
DOI:10.1016/S0960-894X(99)00224-3

Reference yield:

: 229306-00-7
1,2-O-cyclohexylidene (1R,2R,3R,4S,5S)-5-acetamido-4-O-[(2S)-2-O-acetylmandelyl]-1,2,3,4-cyclopentanetetrol

: 229306-17-6
1,2-O-cyclohexylidene (1S,2R,3S,4R)-3-acetamido-4-O-[(2S)-2-O-acetylmandelyl]-1,2,4-cyclopentanetetrol

Guidance literature:: Multi-step reaction with 2 steps

1: 91 percent / DMAP / acetonitrile / 1.5 h / 20 °C

2: 77 percent / nBu₃SnH; AIBN / toluene / 0.5 h / Heating

With dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; acetonitrile; 1: Acylation / 2: Elimination;
DOI:10.1002/(SICI)1099-0690(200005)2000:9<1759::AID-EJOC1759>3.0.CO;2-J

Reference yield:

: 61768-70-5
2,3-O-cyclohexylidene (1,2,3,4,5/0)-5-acetamido-1,2,3,4-cyclopentanetetrol

: 229306-17-6
1,2-O-cyclohexylidene (1S,2R,3S,4R)-3-acetamido-4-O-[(2S)-2-O-acetylmandelyl]-1,2,4-cyclopentanetetrol

Guidance literature:: Multi-step reaction with 4 steps

1: 56 percent / DMAP / CH₂Cl₂ / 0 °C

2: 56 percent / PhOC(S)Cl; DMAP / acetonitrile / 264 h / 20 °C

3: 91 percent / DMAP / acetonitrile / 1.5 h / 20 °C

4: 77 percent / nBu₃SnH; AIBN / toluene / 0.5 h / Heating

With dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; phenylcarbonochloridothioate; In dichloromethane; toluene; acetonitrile; 1: Acylation / 2: Rearrangement / 3: Acylation / 4: Elimination;
DOI:10.1002/(SICI)1099-0690(200005)2000:9<1759::AID-EJOC1759>3.0.CO;2-J