(S)-4-[(R)-((3R,7aR)-3-tert-Butyl-1-oxo-dihydro-pyrrolo[1,2-c]oxazol-7a-yl)-hydroxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Base Information

• Chemical Name: (S)-4-[(R)-((3R,7aR)-3-tert-Butyl-1-oxo-dihydro-pyrrolo[1,2-c]oxazol-7a-yl)-hydroxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester
• CAS No.: 420107-61-5
• Molecular Formula: C₂₄H₃₄N₂O₆
• Molecular Weight: 446.544
• Mol file: 420107-61-5.mol

Synonyms:

Chemical Property of (S)-4-[(R)-((3R,7aR)-3-tert-Butyl-1-oxo-dihydro-pyrrolo[1,2-c]oxazol-7a-yl)-hydroxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-[(R)-((3R,7aR)-3-tert-Butyl-1-oxo-dihydro-pyrrolo[1,2-c]oxazol-7a-yl)-hydroxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

There total 1 articles about (S)-4-[(R)-((3R,7aR)-3-tert-Butyl-1-oxo-dihydro-pyrrolo[1,2-c]oxazol-7a-yl)-hydroxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl 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:

(4S)-3-benzyloxycarbonyl-2,2-dimethyloxazolidine-4-carbaldehyde (117833-92-8) + (3R,7aS)-3-tert-Butyl-tetrahydro-pyrrolo[1,2-c]oxazol-1-one (81286-82-0,119816-46-5) → (S)-4-[(R)-((3R,7aR)-3-tert-Butyl-1-oxo-dihydro-pyrrolo[1,2-c]oxazol-7a-yl)-hydroxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester (420107-61-5) + (S)-4-[(S)-((3R,7aR)-3-tert-Butyl-1-oxo-dihydro-pyrrolo[1,2-c]oxazol-7a-yl)-hydroxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester (420107-71-7)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(01)02255-9

Reference yield:

(S)-4-[(R)-((3R,7aR)-3-tert-Butyl-1-oxo-dihydro-pyrrolo[1,2-c]oxazol-7a-yl)-hydroxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester (420107-61-5) → 4-(3-tert-butyl-1-oxo-dihydro-pyrrolo[1,2-c]oxazole-7a-carbonyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Guidance literature:

With pyridine; Dess-Martin periodane; In dichloromethane; at 0 ℃;

DOI:10.1016/S0040-4039(01)02255-9

Reference yield:

(S)-4-[(R)-((3R,7aR)-3-tert-Butyl-1-oxo-dihydro-pyrrolo[1,2-c]oxazol-7a-yl)-hydroxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester (420107-61-5) → (-)-Kaitocephalin (198710-92-8)

Guidance literature:

Multi-step reaction with 15 steps

1: Dess-Martin periodinane; pyridine / CH₂Cl₂ / 0 °C

2: NaBH₄ / ethanol; tetrahydrofuran / 0 °C

3: aq. H₂SO₄; 1,4-dioxane / 20 - 80 °C

4: DBU / acetonitrile / 20 °C

5: Et₃N; DMAP / CH₂Cl₂ / 20 °C

6: 52 percent / aq. AcOH / 60 °C

7: 96 percent / imidazol / dimethylformamide / 0 °C

8: 84 percent / MeReO₃; urea*H₂O₂ / methanol / 20 °C

9: 75 percent / Zn; CuI / tetrahydrofuran; H₂O / 20 °C / ultrasound irradiation

10: 98 percent / Zn; satd. NH₄Cl / ethanol / 90 °C

11: K₂CO₃ / toluene; H₂O

12: methanol / 20 °C

13: 4-methoxy-TEMPO; KBr; satd. NaHCO₃ / NaClO / CH₂Cl₂ / 0 °C

14: NaClO₂; 2-methyl-2-butene; NaH₂PO₄ / isobutanol; H₂O / 20 °C

15: 27 percent / H₂ / Pd(OH)2-C / ethanol; CHCl₃ / 20 °C

With 1,4-dioxane; pyridine; 1H-imidazole; dmap; 4-methoxy-TEMPO; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; copper(l) iodide; 2-methyl-but-2-ene; sulfuric acid; hydrogen; urea hydrogen peroxide adduct; methyltrioxorhenium(VII); sodium hydrogencarbonate; potassium carbonate; ammonium chloride; Dess-Martin periodane; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; potassium bromide; zinc; sodium hypochlorite; palladium hydroxide - carbon; In tetrahydrofuran; methanol; ethanol; dichloromethane; 2-methyl-propan-1-ol; chloroform; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/S0040-4039(01)02255-9

upstream raw materials:

(4S)-3-benzyloxycarbonyl-2,2-dimethyloxazolidine-4-carbaldehyde

(3R,7aS)-3-tert-Butyl-tetrahydro-pyrrolo[1,2-c]oxazol-1-one

Downstream raw materials:

(S)-4-[(S)-((3R,7aR)-3-tert-Butyl-1-oxo-dihydro-pyrrolo[1,2-c]oxazol-7a-yl)-hydroxy-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

(-)-Kaitocephalin

(R)-2-[(1S,2S)-2-Benzyloxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-1-hydroxy-propyl]-pyrrolidine-2-carboxylic acid benzyl ester

2-[2-benzyloxycarbonylamino-3-(tert-butyl-diphenyl-silanyloxy)-1-trimethylsilanyloxy-propyl]-1-oxy-3,4-dihydro-2H-pyrrole-2-carboxylic acid benzyl ester