O-benzyltilivalline

Base Information

• Chemical Name: O-benzyltilivalline
• CAS No.: 110562-23-7
• Molecular Formula: C₂₇H₂₅N₃O₂
• Molecular Weight: 423.514
• Mol file: 110562-23-7.mol

Synonyms:

Chemical Property of O-benzyltilivalline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-benzyltilivalline

There total 8 articles about O-benzyltilivalline 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:

(S)-2-formylpyrrolidine-1-carboxylic acid benzyl ester (71461-30-8) → O-benzyltilivalline (110562-23-7)

Guidance literature:

Multi-step reaction with 4 steps

1: ceric trichloride / methanol / room temp. for 0.5 h. then 50 gradC for 21 h.

2: H₂ / Pd/C

3: 77 percent / diethyl phosphorocyanidate, triethylamine, molecular sieves 4A / tetrahydrofuran / 0 gradC for 1 h. then room temp. for 40 min.

With cerium(III) chloride; diethyl cyanophosphonate; 4 A molecular sieve; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol;

DOI:10.1016/S0040-4039(00)85411-8

Reference yield:

Cbz-Pro-L-prolinal dimethyl acetal (110562-20-4) → O-benzyltilivalline (110562-23-7)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / Pd/C

2: 77 percent / diethyl phosphorocyanidate, triethylamine, molecular sieves 4A / tetrahydrofuran / 0 gradC for 1 h. then room temp. for 40 min.

With diethyl cyanophosphonate; 4 A molecular sieve; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)85411-8

Reference yield:

2-amino-3-(benzyloxy)benzoic acid (61535-24-8) → O-benzyltilivalline (110562-23-7)

Guidance literature:

Multi-step reaction with 2 steps

1: diethyl phosphorocyanidate, triethylamine / tetrahydrofuran / 1) 0 deg C, 1 h, 2) r.t., 40 min

With diethyl cyanophosphonate; triethylamine; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)80968-6

upstream raw materials:

indole

(2-Amino-3-benzyloxy-phenyl)-((S)-2-dimethoxymethyl-pyrrolidin-1-yl)-methanone

2-amino-3-(benzyloxy)benzoic acid

N-(tert-butoxycarbonyl)-L-prolinol

Downstream raw materials:

tilivalline

Refernces

• 1、 Mori, Shigehiro,Aoyama, Toyohiko,Shioiri, Takayuki. "NEW METHOD AND REAGENTS IN ORGANIC SYNTHESIS. 65. A STEREOSELECTIVE SYNTHESIS OF TILIVALLINE". . p. 6111 - 6114. Retrieved 2007/10/02.