(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

Base Information

• Chemical Name: (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
• CAS No.: 208465-60-5
• Molecular Formula: C₄₄H₅₆IN₃O₇Si
• Molecular Weight: 893.935
• Mol file: 208465-60-5.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 35 articles about (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 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: 97.0%

(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) → (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 (208465-60-5)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; for 6h; Ambient temperature;

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

Reference yield: 95.0%

(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-(chloromethyl)oxazole-4-carbonyl)pyrrolidine-2-carboxylate (1246937-61-0) → (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 (208465-60-5)

Guidance literature:

With sodium iodide; In acetone; at 20 ℃; for 6h; Inert atmosphere; Darkness;

DOI:10.1002/anie.201002220

Reference yield:

methyl (4R,5R,E)-5-hydroxy-4,6-dimethylhept-2-enoate (141901-95-3) → (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 (208465-60-5)

Guidance literature:

Multi-step reaction with 8 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

8: 97 percent / IBX / dimethylsulfoxide / 6 h / Ambient temperature

With dmap; lithium hydroxide; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium iodide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; 1,2-dichloro-ethane; acetone; trifluoroacetic acid;

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

upstream raw materials:

(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

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