D-Glutamic acid, N-[N-[(1,1-dimethylethoxy)carbonyl]-L-alanyl]-, 1-methyl 5-(phenylmethyl) ester

Base Information

• Chemical Name: D-Glutamic acid, N-[N-[(1,1-dimethylethoxy)carbonyl]-L-alanyl]-, 1-methyl 5-(phenylmethyl) ester
• CAS No.: 65671-47-8
• Molecular Formula: C21H30N2O7
• Molecular Weight: 422.478

Synonyms:

Chemical Property of D-Glutamic acid, N-[N-[(1,1-dimethylethoxy)carbonyl]-L-alanyl]-, 1-methyl 5-(phenylmethyl) ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of D-Glutamic acid, N-[N-[(1,1-dimethylethoxy)carbonyl]-L-alanyl]-, 1-methyl 5-(phenylmethyl) ester

There total 7 articles about D-Glutamic acid, N-[N-[(1,1-dimethylethoxy)carbonyl]-L-alanyl]-, 1-methyl 5-(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: 38.0%

L-N-Boc-Ala (15761-38-3) + γ-OBzl-L-Glu-α-OMe (57584-59-5) → (S)-5-benzyl 1-methyl 2-((S)-2-((tert-butoxycarbonyl)amino)propanamido)pentanedioate (65671-47-8)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In chloroform; at 0 ℃;

Reference yield:

L-N-Boc-Ala (15761-38-3) + L-glutamic acid α-methyl γ-benzyl diester hydrochloride (41089-47-8) → (S)-5-benzyl 1-methyl 2-((S)-2-((tert-butoxycarbonyl)amino)propanamido)pentanedioate (65671-47-8)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃; for 22h;

DOI:10.1021/jm00138a013

Reference yield:

D-glutamic acid-5-benzyl ester (2578-33-8,1676-73-9,29456-09-5,25014-27-1) → C21H30N2O7 (65671-47-8)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydrogencarbonate / 1,2-dimethoxyethane; water / 15 h / 20 °C / Inert atmosphere

2: methanol; diethyl ether; hexane / 0.5 h / 0 °C / Inert atmosphere

With sodium hydrogencarbonate; In methanol; 1,2-dimethoxyethane; diethyl ether; hexane; water;

DOI:10.1021/ja2040656

upstream raw materials:

L-N-Boc-Ala

L-glutamic acid α-methyl γ-benzyl diester hydrochloride

benzyl alcohol

L-glutamic acid γ-benzyl ester

Downstream raw materials:

(S)-2-[(S)-2-((S)-4-Benzyloxycarbonyl-2-{(S)-2-[((S)-1-tert-butoxycarbonyl-pyrrolidine-2-carbonyl)-amino]-4-methyl-pentanoylamino}-butyrylamino)-propionylamino]-pentanedioic acid 5-benzyl ester 1-methyl ester

(S)-2-{(S)-2-[(S)-4-Benzyloxycarbonyl-2-((S)-2-tert-butoxycarbonylamino-4-methyl-pentanoylamino)-butyrylamino]-propionylamino}-pentanedioic acid 5-benzyl ester 1-methyl ester

(S)-2-[(S)-2-((S)-4-Benzyloxycarbonyl-2-tert-butoxycarbonylamino-butyrylamino)-propionylamino]-pentanedioic acid 5-benzyl ester 1-methyl ester

(S)-2-((S)-2-Amino-propionylamino)-pentanedioic acid 5-benzyl ester 1-methyl ester; hydrochloride

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