D-Tryptophan, N-[(1,1-dimethylethoxy)carbonyl]-2-methylalanyl-, phenylmethyl ester

Base Information

• Chemical Name: D-Tryptophan, N-[(1,1-dimethylethoxy)carbonyl]-2-methylalanyl-, phenylmethyl ester
• CAS No.: 159634-93-2
• Molecular Formula: C₂₇H₃₃N₃O₅
• Molecular Weight: 479.576
• Mol file: 159634-93-2.mol

Synonyms:

Chemical Property of D-Tryptophan, N-[(1,1-dimethylethoxy)carbonyl]-2-methylalanyl-, phenylmethyl ester

Chemical Property:

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of D-Tryptophan, N-[(1,1-dimethylethoxy)carbonyl]-2-methylalanyl-, phenylmethyl ester

There total 4 articles about D-Tryptophan, N-[(1,1-dimethylethoxy)carbonyl]-2-methylalanyl-, phenylmethyl ester 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:

Boc-Aib-OH (30992-29-1) + D-tryptophan benzyl ester (141595-98-4) → (R)-α-[(2-t-Butoxycarbonylamino-2-methyl-1-oxopropyl)amino]-1H-indole-3-propanoic acid, benzyl ester (159634-93-2)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1016/S0960-894X(98)00103-6

Reference yield:

Boc-D-Trp-OH (5241-64-5) → (R)-α-[(2-t-Butoxycarbonylamino-2-methyl-1-oxopropyl)amino]-1H-indole-3-propanoic acid, benzyl ester (159634-93-2)

Guidance literature:

Multi-step reaction with 3 steps

1: EDC, DMAP / CH₂Cl₂ / 0 °C

2: HCl / ethyl acetate / 0 °C

3: HOBt, EDC / Ambient temperature

With hydrogenchloride; dmap; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In dichloromethane; ethyl acetate;

DOI:10.1016/S0960-894X(98)00238-8

Reference yield:

(R)-2-tert-Butoxycarbonylamino-3-(1H-indol-3-yl)-propionic acid benzyl ester (126090-33-3) → (R)-α-[(2-t-Butoxycarbonylamino-2-methyl-1-oxopropyl)amino]-1H-indole-3-propanoic acid, benzyl ester (159634-93-2)

Guidance literature:

Multi-step reaction with 2 steps

1: HCl / ethyl acetate / 0 °C

2: HOBt, EDC / Ambient temperature

With hydrogenchloride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In ethyl acetate;

DOI:10.1016/S0960-894X(98)00238-8

upstream raw materials:

Boc-Aib-OH

D-tryptophan benzyl ester

Boc-D-Trp-OH

(R)-2-tert-Butoxycarbonylamino-3-(1H-indol-3-yl)-propionic acid benzyl ester

Downstream raw materials:

(R)-2-(2-tert-Butoxycarbonylamino-2-methyl-propionylamino)-3-(1H-indol-3-yl)-propionic acid

Refernces

• 1、 Barakat, Khaled J.,Cheng, Kang,Chan, Wanda W.-S,Butler, Bridget S.,Jacks, Thomas M.,Schleim, Klaus D.,Hora Jr., Donald F.,Hickey, Gerard J.,Smith, Roy G.,Patchett, Arthur A.,Nargund, Ravi P.. "Synthesis and biological activities of phenyl piperazine- based peptidomimetic growth hormone secretagogues". . p. 1431 - 1436. Retrieved 2007/10/03.