(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

Base Information

• Chemical Name: (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
• CAS No.: 208465-70-7
• Molecular Formula: C₄₄H₅₈ClN₃O₇Si
• Molecular Weight: 804.499
• Mol file: 208465-70-7.mol

Synonyms:(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

Chemical Property of (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

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)-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

There total 32 articles about (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 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: 66.0%

(R)-((3R,4R,E)-7-((S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-4-methylocta-2,4-dienylamino)-2,4-dimethyl-7-oxohept-5-en-3-yl) 1-(2-(chloromethyl)-oxazole-4-carbonyl)pyrrolidine-2-carboxylate (208465-69-4) → (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)

Guidance literature:

With acetic acid; In tetrahydrofuran; water; for 7h; 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)-((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)

Guidance literature:

Multi-step reaction with 6 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

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

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

Reference yield:

2-(chloromethyl)oxazole-4-carboxylic acid (208465-62-7) → (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)

Guidance literature:

Multi-step reaction with 4 steps

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

2: 1M LiOH / tetrahydrofuran; H₂O / 6 h / Ambient temperature

3: 77 percent / EDC*HCl, HOBT, NEt₃ / 1,2-dichloro-ethane; H₂O / 5 h / Ambient temperature

4: 66 percent / AcOH / H₂O; tetrahydrofuran / 7 h / Ambient temperature

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

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

upstream raw materials:

(R)-((3R,4R,E)-7-((S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-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)-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

(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

C₄₄H₅₇N₃O₇Si

C₄₄H₅₇N₃O₇Si