(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

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-(chloromethyl)oxazole-4-carbonyl)pyrrolidine-2-carboxylate
• CAS No.: 1246937-61-0
• Molecular Formula: C₄₄H₅₆ClN₃O₇Si
• Molecular Weight: 802.483
• Mol file: 1246937-61-0.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-(chloromethyl)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-(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)-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

There total 22 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-(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: 92.0%

(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)-((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)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; at 20 ℃; for 6h; Inert atmosphere;

DOI:10.1002/anie.201002220

Reference yield:

C6H8N2O2 (159420-55-0) → (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)

Guidance literature:

Multi-step reaction with 8 steps

1.1: dirhodium tetrakis(S-(N-dodecylbenzenesulfonyl)prolinate) / pentane / 24 h / -75 °C / Molecular sieve; Inert atmosphere

2.1: titanium tetrachloride / dichloromethane / 72 h / -20 °C / Inert atmosphere

3.1: trimethylaluminum / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

3.2: 5 h / Inert atmosphere; Reflux

4.1: triisopropoxytitanium(IV) chloride; n-butyllithium; cyclopentylmagnesium chloride / diethyl ether / -78 - -30 °C / Inert atmosphere

5.1: 1H-imidazole / dichloromethane / 3 h / 0 °C / Inert atmosphere

6.1: dmap; 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine / benzene / Inert atmosphere

7.1: camphor-10-sulfonic acid / methanol; dichloromethane / 1 h / 0 °C / Inert atmosphere

8.1: 2-iodoxybenzoic acid / dimethyl sulfoxide / 6 h / Inert atmosphere

8.2: 0.17 h / Inert atmosphere

With 1H-imidazole; triisopropoxytitanium(IV) chloride; dmap; n-butyllithium; dirhodium tetrakis(S-(N-dodecylbenzenesulfonyl)prolinate); 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; 2-iodoxybenzoic acid; trimethylaluminum; titanium tetrachloride; cyclopentylmagnesium chloride; N-ethyl-N,N-diisopropylamine; In methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; pentane; benzene; 4.1: Negishi coupling reaction / 6.1: Yamaguchi reaction;

DOI:10.1021/jo202119p

Reference yield:

methyl (2S,3E)-2-(dimethyl(phenyl)silyl)pent-3-enoate → (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)

Guidance literature:

Multi-step reaction with 7 steps

1.1: titanium tetrachloride / dichloromethane / 72 h / -20 °C / Inert atmosphere

2.1: trimethylaluminum / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

2.2: 5 h / Inert atmosphere; Reflux

3.1: triisopropoxytitanium(IV) chloride; n-butyllithium; cyclopentylmagnesium chloride / diethyl ether / -78 - -30 °C / Inert atmosphere

4.1: 1H-imidazole / dichloromethane / 3 h / 0 °C / Inert atmosphere

5.1: dmap; 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine / benzene / Inert atmosphere

6.1: camphor-10-sulfonic acid / methanol; dichloromethane / 1 h / 0 °C / Inert atmosphere

7.1: 2-iodoxybenzoic acid / dimethyl sulfoxide / 6 h / Inert atmosphere

7.2: 0.17 h / Inert atmosphere

With 1H-imidazole; triisopropoxytitanium(IV) chloride; dmap; n-butyllithium; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; 2-iodoxybenzoic acid; trimethylaluminum; titanium tetrachloride; cyclopentylmagnesium chloride; N-ethyl-N,N-diisopropylamine; In methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; benzene; 3.1: Negishi coupling reaction / 5.1: Yamaguchi reaction;

DOI:10.1021/jo202119p

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

2-dichloromethyl-4,5-dihydrooxazole-4-carboxylic acid methyl ester

C₆H₈N₂O₂

(S)-1-(tert-butyldimethylsilyloxy)hex-4-yn-3-ol

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

C₄₄H₅₇N₃O₇Si

C₄₄H₅₇N₃O₇Si