cis-4-(tert-butyldimethylsilyloxy)-N-benzyloxycarbonyl-D-proline

Base Information

• Chemical Name: cis-4-(tert-butyldimethylsilyloxy)-N-benzyloxycarbonyl-D-proline
• CAS No.: 329188-63-8
• Molecular Formula: C₁₉H₂₉NO₅Si
• Molecular Weight: 379.528
• Mol file: 329188-63-8.mol

Synonyms:cis-4-(tert-butyldimethylsilyloxy)-N-benzyloxycarbonyl-D-proline

Chemical Property of cis-4-(tert-butyldimethylsilyloxy)-N-benzyloxycarbonyl-D-proline

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of cis-4-(tert-butyldimethylsilyloxy)-N-benzyloxycarbonyl-D-proline

There total 1 articles about cis-4-(tert-butyldimethylsilyloxy)-N-benzyloxycarbonyl-D-proline 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:

tert-butyldimethylsilyl chloride (18162-48-6) + (R,R)-4-hydroxy-1-(benzyloxycarbonyl)pyrrolidine-2-carboxylic acid (130930-25-5) → cis-4-(tert-butyldimethylsilyloxy)-N-benzyloxycarbonyl-D-proline (329188-63-8)

Guidance literature:

With 1H-imidazole; In DMF (N,N-dimethyl-formamide); at 5 - 20 ℃; for 16h;

Reference yield: 63.0%

cis-4-(tert-butyldimethylsilyloxy)-N-benzyloxycarbonyl-D-proline (329188-63-8) + 2-methyl-1-(trimethylsilyloxy)-1-propene (6651-34-9) → (2R,4R)-benzyl 4-(tert-butyldimethylsilyloxy)-2-(2-methyl-1-oxopropan-2-yl)pyrrolidine-1-carboxylate (1378239-21-4) + (2S,4R)-benzyl 4-(tert-butyldimethylsilyloxy)-2-(2-methyl-1-oxo propan-2-yl)pyrrolidine-1-carboxylate (1378239-22-5)

Guidance literature:

cis-4-(tert-butyldimethylsilyloxy)-N-benzyloxycarbonyl-D-proline; With [bis(acetoxy)iodo]benzene; iodine; In dichloromethane; at 25 - 26 ℃; for 4h; Irradiation; Inert atmosphere;

2-methyl-1-(trimethylsilyloxy)-1-propene; With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 20 ℃; for 3h; Inert atmosphere;

DOI:10.1039/c2ob25433f

Reference yield:

cis-4-(tert-butyldimethylsilyloxy)-N-benzyloxycarbonyl-D-proline (329188-63-8) + 2-hydroxy-2-phenylacetophenone (119-53-9,579-44-2) → cis-4-(tert-butyldimethylsilyloxy)-N-benzyloxycarbonyl-D-proline 2-oxo-1,2-diphenylethyl ester (329188-64-9)

Guidance literature:

With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; at 5 - 20 ℃; for 20h;

upstream raw materials:

tert-butyldimethylsilyl chloride

(R,R)-4-hydroxy-1-(benzyloxycarbonyl)pyrrolidine-2-carboxylic acid

Downstream raw materials:

cis-4-(tert-butyldimethylsilyloxy)-N-benzyloxycarbonyl-D-proline 2-oxo-1,2-diphenylethyl ester

(2R,4R)-benzyl 4-(tert-butyldimethylsilyloxy)-2-(2-methyl-1-oxopropan-2-yl)pyrrolidine-1-carboxylate

(2S,4R)-benzyl 4-(tert-butyldimethylsilyloxy)-2-(2-methyl-1-oxo propan-2-yl)pyrrolidine-1-carboxylate