(R)-1-(2-Iodomethyl-oxazole-4-carbonyl)-pyrrolidine-2-carboxylic acid (E)-(1R,2R)-4-[(2E,4E)-(S)-6-(tert-butyl-diphenyl-silanyloxy)-8-hydroxy-4-methyl-octa-2,4-dienylcarbamoyl]-1-isopropyl-2-methyl-but-3-enyl ester

Base Information

• Chemical Name: (R)-1-(2-Iodomethyl-oxazole-4-carbonyl)-pyrrolidine-2-carboxylic acid (E)-(1R,2R)-4-[(2E,4E)-(S)-6-(tert-butyl-diphenyl-silanyloxy)-8-hydroxy-4-methyl-octa-2,4-dienylcarbamoyl]-1-isopropyl-2-methyl-but-3-enyl ester
• CAS No.: 208465-71-8
• Molecular Formula: C₄₄H₅₈IN₃O₇Si
• Molecular Weight: 895.95
• Mol file: 208465-71-8.mol

Synonyms:(R)-1-(2-Iodomethyl-oxazole-4-carbonyl)-pyrrolidine-2-carboxylic acid (E)-(1R,2R)-4-[(2E,4E)-(S)-6-(tert-butyl-diphenyl-silanyloxy)-8-hydroxy-4-methyl-octa-2,4-dienylcarbamoyl]-1-isopropyl-2-methyl-but-3-enyl ester

Chemical Property of (R)-1-(2-Iodomethyl-oxazole-4-carbonyl)-pyrrolidine-2-carboxylic acid (E)-(1R,2R)-4-[(2E,4E)-(S)-6-(tert-butyl-diphenyl-silanyloxy)-8-hydroxy-4-methyl-octa-2,4-dienylcarbamoyl]-1-isopropyl-2-methyl-but-3-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-(2-Iodomethyl-oxazole-4-carbonyl)-pyrrolidine-2-carboxylic acid (E)-(1R,2R)-4-[(2E,4E)-(S)-6-(tert-butyl-diphenyl-silanyloxy)-8-hydroxy-4-methyl-octa-2,4-dienylcarbamoyl]-1-isopropyl-2-methyl-but-3-enyl ester

There total 16 articles about (R)-1-(2-Iodomethyl-oxazole-4-carbonyl)-pyrrolidine-2-carboxylic acid (E)-(1R,2R)-4-[(2E,4E)-(S)-6-(tert-butyl-diphenyl-silanyloxy)-8-hydroxy-4-methyl-octa-2,4-dienylcarbamoyl]-1-isopropyl-2-methyl-but-3-enyl 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: 100.0%

(R)-((3R,4R,E)-7-((S,2E,4E)-6-(tert-butyldiphenylsilyloxy)-8-hydroxy-4-methylocta-2,4-dienylamino)-2,4-dimethyl-7-oxohept-5-en-3-yl) 1-(2-(chloromethyl)oxazole-4-carbonyl)pyrrolidine-2-carboxylate (208465-70-7) → (R)-1-(2-Iodomethyl-oxazole-4-carbonyl)-pyrrolidine-2-carboxylic acid (E)-(1R,2R)-4-[(2E,4E)-(S)-6-(tert-butyl-diphenyl-silanyloxy)-8-hydroxy-4-methyl-octa-2,4-dienylcarbamoyl]-1-isopropyl-2-methyl-but-3-enyl ester (208465-71-8)

Guidance literature:

With sodium iodide; In acetone; for 6h; Ambient temperature;

DOI:10.1016/S0040-4039(98)00499-7

Reference yield:

methyl (4R,5R,E)-5-hydroxy-4,6-dimethylhept-2-enoate (141901-95-3) → (R)-1-(2-Iodomethyl-oxazole-4-carbonyl)-pyrrolidine-2-carboxylic acid (E)-(1R,2R)-4-[(2E,4E)-(S)-6-(tert-butyl-diphenyl-silanyloxy)-8-hydroxy-4-methyl-octa-2,4-dienylcarbamoyl]-1-isopropyl-2-methyl-but-3-enyl ester (208465-71-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 94 percent / EDC*HCl, DMAP / CH₂Cl₂ / 5 h / Ambient temperature

2: 96 percent / trifluoroacetic acid / 0.5 h / 0 °C

3: 74 percent / EDC*HCl, HOBT, NEt₃ / 1,2-dichloro-ethane; H₂O / 5 h / Ambient temperature

4: 1M LiOH / tetrahydrofuran; H₂O / 6 h / Ambient temperature

5: 77 percent / EDC*HCl, HOBT, NEt₃ / 1,2-dichloro-ethane; H₂O / 5 h / Ambient temperature

6: 66 percent / AcOH / H₂O; tetrahydrofuran / 7 h / Ambient temperature

7: 100 percent / NaI / acetone / 6 h / Ambient temperature

With dmap; lithium hydroxide; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium iodide; In tetrahydrofuran; dichloromethane; water; 1,2-dichloro-ethane; acetone; trifluoroacetic acid;

DOI:10.1016/S0040-4039(98)00499-7

Reference yield:

(2S,3R)-1-Benzenesulfonyl-2,4-dimethyl-pentan-3-ol (141859-95-2) → (R)-1-(2-Iodomethyl-oxazole-4-carbonyl)-pyrrolidine-2-carboxylic acid (E)-(1R,2R)-4-[(2E,4E)-(S)-6-(tert-butyl-diphenyl-silanyloxy)-8-hydroxy-4-methyl-octa-2,4-dienylcarbamoyl]-1-isopropyl-2-methyl-but-3-enyl ester (208465-71-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 88 percent / PPTS / CH₂Cl₂ / 72 h / Ambient temperature

2: LDA, HMPT / tetrahydrofuran / 3.5 h / -78 deg C to rt

3: diethyl ether / 1 h / 0 °C

4: CAN / H₂O; CH₂Cl₂

5: 94 percent / EDC*HCl, DMAP / CH₂Cl₂ / 5 h / Ambient temperature

6: 96 percent / trifluoroacetic acid / 0.5 h / 0 °C

7: 74 percent / EDC*HCl, HOBT, NEt₃ / 1,2-dichloro-ethane; H₂O / 5 h / Ambient temperature

8: 1M LiOH / tetrahydrofuran; H₂O / 6 h / Ambient temperature

9: 77 percent / EDC*HCl, HOBT, NEt₃ / 1,2-dichloro-ethane; H₂O / 5 h / Ambient temperature

10: 66 percent / AcOH / H₂O; tetrahydrofuran / 7 h / Ambient temperature

11: 100 percent / NaI / acetone / 6 h / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium hydroxide; ammonium cerium(IV) nitrate; pyridinium p-toluenesulfonate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium iodide; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; water; 1,2-dichloro-ethane; acetone; trifluoroacetic acid;

DOI:10.1016/S0040-4039(98)00499-7

upstream raw materials:

(R)-((3R,4R,E)-7-((S,2E,4E)-6-(tert-butyldiphenylsilyloxy)-8-hydroxy-4-methylocta-2,4-dienylamino)-2,4-dimethyl-7-oxohept-5-en-3-yl) 1-(2-(chloromethyl)oxazole-4-carbonyl)pyrrolidine-2-carboxylate

methyl (4R,5R,E)-5-hydroxy-4,6-dimethylhept-2-enoate

(2S,3R)-1-Benzenesulfonyl-2,4-dimethyl-pentan-3-ol

(R)-Pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-((E)-(1R,2R)-1-isopropyl-4-methoxycarbonyl-2-methyl-but-3-enyl) ester

Downstream raw materials:

(R)-((3R,4R,E)-7-((S,2E,4E)-6-(tert-butyldiphenylsilyloxy)-4-methyl-8-oxoocta-2,4-dienylamino)-2,4-dimethyl-7-oxohept-5-en-3-yl) 1-(2-(iodomethyl)oxazole-4-carbonyl)pyrrolidine-2-carboxylate