(4S,5S)-3-(tert-butoxycarbonyl)-4-(cyclohexylmethyl)-2,2-dimethyloxazolidine-5-ethanol

Base Information

• Chemical Name: (4S,5S)-3-(tert-butoxycarbonyl)-4-(cyclohexylmethyl)-2,2-dimethyloxazolidine-5-ethanol
• CAS No.: 124577-55-5
• Molecular Formula: C₁₉H₃₅NO₄
• Molecular Weight: 341.491
• Mol file: 124577-55-5.mol

Synonyms:(4S,5S)-3-(tert-butoxycarbonyl)-4-(cyclohexylmethyl)-2,2-dimethyloxazolidine-5-ethanol

Chemical Property of (4S,5S)-3-(tert-butoxycarbonyl)-4-(cyclohexylmethyl)-2,2-dimethyloxazolidine-5-ethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-3-(tert-butoxycarbonyl)-4-(cyclohexylmethyl)-2,2-dimethyloxazolidine-5-ethanol

There total 3 articles about (4S,5S)-3-(tert-butoxycarbonyl)-4-(cyclohexylmethyl)-2,2-dimethyloxazolidine-5-ethanol 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:

(4S,5S)-3-(tert-butoxycarbonyl)-4-cyclohexylmethyl-5-formylmethyl-2,2-dimethyl-1,3-oxazolidine (145341-80-6) → (4S,5S)-3-(tert-butoxycarbonyl)-4-(cyclohexylmethyl)-2,2-dimethyloxazolidine-5-ethanol (124577-55-5)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 3h; Yield given;

DOI:10.1021/jm00097a010

Reference yield:

(4S,5S)-5-allyl-3-(tert-butoxycarbonyl)-4-(cyclohexylmethyl)-2,2-dimethyloxazolidine (143122-11-6) → (4S,5S)-3-(tert-butoxycarbonyl)-4-(cyclohexylmethyl)-2,2-dimethyloxazolidine-5-ethanol (124577-55-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) ozone, 2.) Me₂S / 1.) GH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, RT, overnight

2: sodium borohydride / methanol / 3 h / 0 °C

With sodium tetrahydroborate; dimethylsulfide; ozone; In methanol;

DOI:10.1021/jm00097a010

Reference yield:

(2S,3S)-2-(tert-butoxycarboxamido)-1-cyclohexyl-5-hexen-3-ol (104882-44-2) → (4S,5S)-3-(tert-butoxycarbonyl)-4-(cyclohexylmethyl)-2,2-dimethyloxazolidine-5-ethanol (124577-55-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / p-toluenesulfonic acid (PTSA) / CH₂Cl₂ / 14 h / Ambient temperature

2: 1.) ozone, 2.) Me₂S / 1.) GH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, RT, overnight

3: sodium borohydride / methanol / 3 h / 0 °C

With sodium tetrahydroborate; dimethylsulfide; toluene-4-sulfonic acid; ozone; In methanol; dichloromethane;

DOI:10.1021/jm00097a010

upstream raw materials:

(4S,5S)-3-(tert-butoxycarbonyl)-4-cyclohexylmethyl-5-formylmethyl-2,2-dimethyl-1,3-oxazolidine

(4S,5S)-5-allyl-3-(tert-butoxycarbonyl)-4-(cyclohexylmethyl)-2,2-dimethyloxazolidine

(2S,3S)-2-(tert-butoxycarboxamido)-1-cyclohexyl-5-hexen-3-ol

Downstream raw materials:

((S)-1-{(S)-1-[(1S,2S)-1-Cyclohexylmethyl-2-hydroxy-4-(pyridin-2-ylsulfanyl)-butylcarbamoyl]-2-[1-(2,4-dinitro-phenyl)-1H-imidazol-4-yl]-ethylcarbamoyl}-2-phenyl-ethyl)-carbamic acid tert-butyl ester

(2S,3S)-2-<<(2S)-2-<<(4-aminopiperidino)carbonyl>oxy>-3-phenylpropionyl>-Ala-amino>-1-cyclohexyl-5-(2-pyridylthio)-3-pentanol bis(trifluoroacetate)

4-tert-Butoxycarbonylamino-piperidine-1-carboxylic acid (S)-1-{(S)-1-[(1S,2S)-1-cyclohexylmethyl-2-hydroxy-4-(pyridin-2-ylsulfanyl)-butylcarbamoyl]-2-[1-(2,4-dinitro-phenyl)-1H-imidazol-4-yl]-ethylcarbamoyl}-2-phenyl-ethyl ester

(2S,3S)-2-<<(2S)-2-<<(4-aminopiperidino)carbonyl>oxy>-3-phenylpropionyl>-Nva-amino>-1-cyclohexyl-5-(2-pyridylthio)-3-pentanol bis(trifluoroacetate)