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

Base Information

Chemical Name:1,2-O-cyclohexylidene (1R,2R,3S,4S)-4-acetamido-3-O-[(2S)-2-O-acetylmandelyl]-1,2,3-cyclopentanetriol
CAS No.:229310-06-9
Molecular Formula:C₂₃H₂₉NO₇
Molecular Weight:431.486
Hs Code.:

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

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

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

There total 3 articles about 1,2-O-cyclohexylidene (1R,2R,3S,4S)-4-acetamido-3-O-[(2S)-2-O-acetylmandelyl]-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: 71.0%

: 229306-01-8
2,3-O-cyclohexylidene (1S,2R,3S,4R,5R)-5-acetamido-1-O-[(2S)-2-O-acetylmandelyl]-4-O-phenoxythiocarbonyl-1,2,3,4-cyclopentanetetrol

: 229310-06-9
1,2-O-cyclohexylidene (1R,2R,3S,4S)-4-acetamido-3-O-[(2S)-2-O-acetylmandelyl]-1,2,3-cyclopentanetriol

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 1h; Heating;
DOI:10.1016/S0960-894X(99)00224-3

Reference yield:

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

: 229310-06-9
1,2-O-cyclohexylidene (1R,2R,3S,4S)-4-acetamido-3-O-[(2S)-2-O-acetylmandelyl]-1,2,3-cyclopentanetriol

Guidance literature:: Multi-step reaction with 3 steps

1: 56 percent / DMAP / CH₂Cl₂ / 0 °C

2: 71 percent / DMAP / acetonitrile / 3 h / 20 °C

3: 71 percent / nBu₃SnCl; AIBN / toluene / 2 h / Heating

With dmap; 2,2'-azobis(isobutyronitrile); tributyltin chloride; In dichloromethane; toluene; acetonitrile; 1: Acylation / 2: Acylation / 3: Elimination;
DOI:10.1002/(SICI)1099-0690(200005)2000:9<1759::AID-EJOC1759>3.0.CO;2-J

Reference yield:

: 171031-89-3
2,3-O-cyclohexylidene (1S,2R,3R,4R,5S)-5-acetamido-1-O-[(2S)-2-O-acetylmandelyl]-1,2,3,4-cyclohexanetetrol

: 229310-06-9
1,2-O-cyclohexylidene (1R,2R,3S,4S)-4-acetamido-3-O-[(2S)-2-O-acetylmandelyl]-1,2,3-cyclopentanetriol

Guidance literature:: Multi-step reaction with 2 steps

1: 71 percent / DMAP / acetonitrile / 3 h / 20 °C

2: 71 percent / nBu₃SnCl; AIBN / toluene / 2 h / Heating

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