(4S,5R)-4-Cyclohexylmethyl-2,2-dimethyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-(4-iodo-butyl) ester

Base Information

• Chemical Name: (4S,5R)-4-Cyclohexylmethyl-2,2-dimethyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-(4-iodo-butyl) ester
• CAS No.: 135913-21-2
• Molecular Formula: C₂₂H₃₈INO₅
• Molecular Weight: 523.452
• Mol file: 135913-21-2.mol

Synonyms:(4S,5R)-4-Cyclohexylmethyl-2,2-dimethyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-(4-iodo-butyl) ester

Chemical Property of (4S,5R)-4-Cyclohexylmethyl-2,2-dimethyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-(4-iodo-butyl) ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R)-4-Cyclohexylmethyl-2,2-dimethyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-(4-iodo-butyl) ester

There total 1 articles about (4S,5R)-4-Cyclohexylmethyl-2,2-dimethyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-(4-iodo-butyl) ester 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: 90.0%

1,4-Diiodobutane (628-21-7) + (4S,5R)-3-tert-Butoxycarbonyl-4-cyclohexyl-methyl-2,2-dimethyloxazolidine-5-carboxylic acid (121533-54-8) → (4S,5R)-4-Cyclohexylmethyl-2,2-dimethyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-(4-iodo-butyl) ester (135913-21-2)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; for 2h; Ambient temperature;

DOI:10.1016/S0040-4039(00)61590-3

Reference yield:

(4S,5R)-4-Cyclohexylmethyl-2,2-dimethyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-(4-iodo-butyl) ester (135913-21-2) → (S)-2-Benzyl-N-((3R,4S,7R)-4-cyclohexylmethyl-3-hydroxy-2,6-dioxo-1-oxa-9-thia-5-aza-cyclotridec-7-yl)-3-(2-methyl-propane-2-sulfonyl)-propionamide (135913-25-6)

Guidance literature:

Multi-step reaction with 6 steps

1: i-Pr₂NEt / ethanol; H₂O / 12 h / Ambient temperature

2: NaHCO₃ / H₂O; dioxane / 2 h / Ambient temperature

3: TFA / 0.5 h / Ambient temperature

4: EDC, DMAP, DMAP*HCl / CH₂Cl₂; tetrahydrofuran / Heating

5: DMS, TFA / Ambient temperature

6: EDC, HOBT, NMM / 4 h / 0 °C

With 4-methyl-morpholine; dmap; 2,3-dimercapto-succinic acid; 4-(dimethylamino)pyridine hydrochloride; sodium hydrogencarbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water;

DOI:10.1016/S0040-4039(00)61590-3

Reference yield:

(4S,5R)-4-Cyclohexylmethyl-2,2-dimethyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-(4-iodo-butyl) ester (135913-21-2) → [(S)-1-((3R,4S,7R)-4-Cyclohexylmethyl-3-hydroxy-2,6-dioxo-1-oxa-9-thia-5-aza-cyclotridec-7-ylcarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester

Guidance literature:

Multi-step reaction with 6 steps

1: i-Pr₂NEt / ethanol; H₂O / 12 h / Ambient temperature

2: NaHCO₃ / H₂O; dioxane / 2 h / Ambient temperature

3: TFA / 0.5 h / Ambient temperature

4: EDC, DMAP, DMAP*HCl / CH₂Cl₂; tetrahydrofuran / Heating

5: DMS, TFA / Ambient temperature

6: EDC, HOBT, NMM / 4 h / 0 °C

With 4-methyl-morpholine; dmap; 2,3-dimercapto-succinic acid; 4-(dimethylamino)pyridine hydrochloride; sodium hydrogencarbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water;

DOI:10.1016/S0040-4039(00)61590-3

upstream raw materials:

1,4-Diiodobutane

(4S,5R)-3-tert-Butoxycarbonyl-4-cyclohexyl-methyl-2,2-dimethyloxazolidine-5-carboxylic acid

Downstream raw materials:

(4S,5R)-4-Cyclohexylmethyl-2,2-dimethyl-oxazolidine-3,5-dicarboxylic acid 5-[4-((R)-2-amino-2-carboxy-ethylsulfanyl)-butyl] ester 3-tert-butyl ester

((3R,4S,7R)-4-Cyclohexylmethyl-3-hydroxy-2,6-dioxo-1-oxa-9-thia-5-aza-cyclotridec-7-yl)-carbamic acid benzyl ester

(S)-2-Benzyl-N-((3R,4S,7R)-4-cyclohexylmethyl-3-hydroxy-2,6-dioxo-1-oxa-9-thia-5-aza-cyclotridec-7-yl)-3-(2-methyl-propane-2-sulfonyl)-propionamide

(4S,5R)-4-Cyclohexylmethyl-2,2-dimethyl-oxazolidine-3,5-dicarboxylic acid 5-[4-((R)-2-benzyloxycarbonylamino-2-carboxy-ethylsulfanyl)-butyl] ester 3-tert-butyl ester