methyl (2R)-2-[(S)-1-{[(benzyloxy)carbonyl]amino}-1-(phenylmethyl)carboxamido]-2-(3,5-dihydroxy-4-methoxyphenyl)ethanoate

Base Information

Chemical Name:methyl (2R)-2-[(S)-1-{[(benzyloxy)carbonyl]amino}-1-(phenylmethyl)carboxamido]-2-(3,5-dihydroxy-4-methoxyphenyl)ethanoate
CAS No.:208448-13-9
Molecular Formula:C₂₆H₂₆N₂O₈
Molecular Weight:494.501
Hs Code.:

Synonyms:methyl (2R)-2-[(S)-1-{[(benzyloxy)carbonyl]amino}-1-(phenylmethyl)carboxamido]-2-(3,5-dihydroxy-4-methoxyphenyl)ethanoate

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Chemical Property of methyl (2R)-2-[(S)-1-{[(benzyloxy)carbonyl]amino}-1-(phenylmethyl)carboxamido]-2-(3,5-dihydroxy-4-methoxyphenyl)ethanoate

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Technology Process of methyl (2R)-2-[(S)-1-{[(benzyloxy)carbonyl]amino}-1-(phenylmethyl)carboxamido]-2-(3,5-dihydroxy-4-methoxyphenyl)ethanoate

There total 3 articles about methyl (2R)-2-[(S)-1-{[(benzyloxy)carbonyl]amino}-1-(phenylmethyl)carboxamido]-2-(3,5-dihydroxy-4-methoxyphenyl)ethanoate 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:

: 191542-07-1
(2R)-2-azido-2-[3,5-bis(benzyloxy)-4-methoxyphenyl]ethanoic acid

: 208448-13-9
methyl (2R)-2-[(S)-1-{[(benzyloxy)carbonyl]amino}-1-(phenylmethyl)carboxamido]-2-(3,5-dihydroxy-4-methoxyphenyl)ethanoate

Guidance literature:: Multi-step reaction with 3 steps

1: 95 percent / p-toluenesulfonic acid monohydrate / 2.5 h / Heating

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

3: 590 mg / HOAt; EDCI; TMP / dimethylformamide; CH₂Cl₂ / 13 h / 0 - 20 °C

With hydrogenchloride; 1-hydroxy-7-aza-benzotriazole; hydrogen; toluene-4-sulfonic acid; thymidine 5'-phosphate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Esterification / 2: Hydrogenolysis / 3: Acylation;
DOI:10.1021/jo980060b

Reference yield:

: 208448-12-8
methyl (2R)-2-azido-2-[3,5-bis(benzyloxy)-4-methoxyphenyl]ethanoate

: 208448-13-9
methyl (2R)-2-[(S)-1-{[(benzyloxy)carbonyl]amino}-1-(phenylmethyl)carboxamido]-2-(3,5-dihydroxy-4-methoxyphenyl)ethanoate

Guidance literature:: Multi-step reaction with 2 steps

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

2: 590 mg / HOAt; EDCI; TMP / dimethylformamide; CH₂Cl₂ / 13 h / 0 - 20 °C

With hydrogenchloride; 1-hydroxy-7-aza-benzotriazole; hydrogen; thymidine 5'-phosphate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Hydrogenolysis / 2: Acylation;
DOI:10.1021/jo980060b

Reference yield:

: 5491-18-9,17609-52-8,53990-33-3,60584-76-1
(S)-N-(benzyloxycarbonyl)phenylglycine

: (R)-Amino-(3,5-dihydroxy-4-methoxy-phenyl)-acetic acid methyl ester; hydrochloride

: 208448-13-9
methyl (2R)-2-[(S)-1-{[(benzyloxy)carbonyl]amino}-1-(phenylmethyl)carboxamido]-2-(3,5-dihydroxy-4-methoxyphenyl)ethanoate

Guidance literature:: With 1-hydroxy-7-aza-benzotriazole; thymidine 5'-phosphate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20 ℃; for 13h;
DOI:10.1021/jo980060b