(4S,5R)-4-cyclohexylmethyl-5-<(1R)-2-acetoxy-1-iodoethyl>oxazolidin-2-one

Base Information

Chemical Name:(4S,5R)-4-cyclohexylmethyl-5-<(1R)-2-acetoxy-1-iodoethyl>oxazolidin-2-one
CAS No.:166272-36-2
Molecular Formula:C₁₄H₂₂INO₄
Molecular Weight:395.237
Hs Code.:

Synonyms:(4S,5R)-4-cyclohexylmethyl-5-<(1R)-2-acetoxy-1-iodoethyl>oxazolidin-2-one

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Chemical Property of (4S,5R)-4-cyclohexylmethyl-5-<(1R)-2-acetoxy-1-iodoethyl>oxazolidin-2-one

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Technology Process of (4S,5R)-4-cyclohexylmethyl-5-<(1R)-2-acetoxy-1-iodoethyl>oxazolidin-2-one

There total 5 articles about (4S,5R)-4-cyclohexylmethyl-5-<(1R)-2-acetoxy-1-iodoethyl>oxazolidin-2-one 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: 96.6%

: 166272-35-1
cis-(4S)-(N-benzyloxycarbonyl)amino-5-cyclohexyl-2-pentenol acetate

: 166272-36-2
(4S,5R)-4-cyclohexylmethyl-5-<(1R)-2-acetoxy-1-iodoethyl>oxazolidin-2-one

Guidance literature:: With iodine; In acetonitrile; Ambient temperature;
DOI:10.1248/cpb.42.2164

Reference yield:

: 105852-47-9
2-<(benzyloxycarbonyl)amino>-3-cyclohexyl-(2S)-propionaldehyde

: 166272-36-2
(4S,5R)-4-cyclohexylmethyl-5-<(1R)-2-acetoxy-1-iodoethyl>oxazolidin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: potassium bis(trimethylsilyl)amide, 18-crown-6 / tetrahydrofuran; toluene / 1 h / -78 °C

2: 1.) BF₃*Et₂O, 2.) diisobutylaluminum hydride / 1.) CH₂Cl₂, -78 deg C, 40 min, 2.) CH₂Cl₂, toluene, -78 deg C, 1.2 h

3: 92 percent / pyridine, N,N-dimethylaminopyridine / Ambient temperature

4: 96.6 percent / iodine / acetonitrile / Ambient temperature

With pyridine; dmap; 18-crown-6 ether; boron trifluoride diethyl etherate; iodine; potassium hexamethylsilazane; diisobutylaluminium hydride; In tetrahydrofuran; toluene; acetonitrile;
DOI:10.1248/cpb.42.2164

Reference yield:

: 118388-23-1
N',O-dimethyl-N-benzyloxycarbonyl-L-cyclohexylalanine hydroxamate

: 166272-36-2
(4S,5R)-4-cyclohexylmethyl-5-<(1R)-2-acetoxy-1-iodoethyl>oxazolidin-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: LiAlH₄ / diethyl ether / 0.5 h / Ambient temperature

2: potassium bis(trimethylsilyl)amide, 18-crown-6 / tetrahydrofuran; toluene / 1 h / -78 °C

3: 1.) BF₃*Et₂O, 2.) diisobutylaluminum hydride / 1.) CH₂Cl₂, -78 deg C, 40 min, 2.) CH₂Cl₂, toluene, -78 deg C, 1.2 h

4: 92 percent / pyridine, N,N-dimethylaminopyridine / Ambient temperature

5: 96.6 percent / iodine / acetonitrile / Ambient temperature

With pyridine; dmap; lithium aluminium tetrahydride; 18-crown-6 ether; boron trifluoride diethyl etherate; iodine; potassium hexamethylsilazane; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; toluene; acetonitrile;
DOI:10.1248/cpb.42.2164