(2R)-2-{(R)-1-[(S)-1-[(tert-butoxycarbonyl)amino]-1-(phenylmethyl)carboxamido]-1-[[3,5-bis(benzyloxy)-4-methoxyphenyl]methyl]carboxamido}-2-phenylethanoic acid

Base Information

Chemical Name:(2R)-2-{(R)-1-[(S)-1-[(tert-butoxycarbonyl)amino]-1-(phenylmethyl)carboxamido]-1-[[3,5-bis(benzyloxy)-4-methoxyphenyl]methyl]carboxamido}-2-phenylethanoic acid
CAS No.:208448-37-7
Molecular Formula:C₄₄H₄₅N₃O₉
Molecular Weight:759.856
Hs Code.:

(2R)-2-{(R)-1-[(S)-1-[(tert-butoxycarbonyl)amino]-1-(phenylmethyl)carboxamido]-1-[[3,5-bis(benzyloxy)-4-methoxyphenyl]methyl]carboxamido}-2-phenylethanoic acid

Synonyms:(2R)-2-{(R)-1-[(S)-1-[(tert-butoxycarbonyl)amino]-1-(phenylmethyl)carboxamido]-1-[[3,5-bis(benzyloxy)-4-methoxyphenyl]methyl]carboxamido}-2-phenylethanoic acid

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Chemical Property of (2R)-2-{(R)-1-[(S)-1-[(tert-butoxycarbonyl)amino]-1-(phenylmethyl)carboxamido]-1-[[3,5-bis(benzyloxy)-4-methoxyphenyl]methyl]carboxamido}-2-phenylethanoic acid

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Technology Process of (2R)-2-{(R)-1-[(S)-1-[(tert-butoxycarbonyl)amino]-1-(phenylmethyl)carboxamido]-1-[[3,5-bis(benzyloxy)-4-methoxyphenyl]methyl]carboxamido}-2-phenylethanoic acid

There total 9 articles about (2R)-2-{(R)-1-[(S)-1-[(tert-butoxycarbonyl)amino]-1-(phenylmethyl)carboxamido]-1-[[3,5-bis(benzyloxy)-4-methoxyphenyl]methyl]carboxamido}-2-phenylethanoic acid 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: 93.0%

: 208448-36-6
2-(trimethylsilyl)ethyl (2R)-2-{(R)-1-[(S)-1-[(tert-butoxycarbonyl)amino]-1-(phenylmethyl)carboxamido]-1-[[3,5-bis(benzyloxy)-4-methoxyphenyl]methyl]carboxamido}-2-phenylethanoate

: 208448-37-7
(2R)-2-{(R)-1-[(S)-1-[(tert-butoxycarbonyl)amino]-1-(phenylmethyl)carboxamido]-1-[[3,5-bis(benzyloxy)-4-methoxyphenyl]methyl]carboxamido}-2-phenylethanoic acid

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 8h;
DOI:10.1021/jo980060b

Reference yield:

: 2900-27-8
(2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethanoic acid

: 208448-37-7
(2R)-2-{(R)-1-[(S)-1-[(tert-butoxycarbonyl)amino]-1-(phenylmethyl)carboxamido]-1-[[3,5-bis(benzyloxy)-4-methoxyphenyl]methyl]carboxamido}-2-phenylethanoic acid

Guidance literature:: Multi-step reaction with 2 steps

1: 91 percent / HOAt; EDCI / dimethylformamide; CH₂Cl₂ / 15 h / 0 - 20 °C

2: 93 percent / TBAF / tetrahydrofuran / 8 h / 20 °C

With 1-hydroxy-7-aza-benzotriazole; tetrabutyl ammonium fluoride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1: Acylation / 2: deprotection;
DOI:10.1021/jo980060b

Reference yield:

: 17609-52-8
Z-D-phenylglycine

: 208448-37-7
(2R)-2-{(R)-1-[(S)-1-[(tert-butoxycarbonyl)amino]-1-(phenylmethyl)carboxamido]-1-[[3,5-bis(benzyloxy)-4-methoxyphenyl]methyl]carboxamido}-2-phenylethanoic acid

Guidance literature:: Multi-step reaction with 6 steps

1: 85 percent / DMAP; DCC / CH₂Cl₂ / 4 h / 0 °C

2: 96 percent / aq. HCl; H₂ / Pd-C / tetrahydrofuran; methanol / 18 h / 760 Torr

3: 90 percent / HOAt; TMP; DCC / CH₂Cl₂ / 15 h / 0 - 20 °C

4: 98 percent / SnCl₂ / tetrahydrofuran; methanol / 5.25 h / 0 - 20 °C

5: 91 percent / HOAt; EDCI / dimethylformamide; CH₂Cl₂ / 15 h / 0 - 20 °C

6: 93 percent / TBAF / tetrahydrofuran / 8 h / 20 °C

With hydrogenchloride; dmap; 1-hydroxy-7-aza-benzotriazole; tetrabutyl ammonium fluoride; hydrogen; thymidine 5'-phosphate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dicyclohexyl-carbodiimide; tin(ll) chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Esterification / 2: Hydrogenolysis / 3: Acylation / 4: Reduction / 5: Acylation / 6: deprotection;
DOI:10.1021/jo980060b