(9S,12S,15S)-4-Benzyloxy-9-benzyloxycarbonylamino-12-carbamoylmethyl-10,13-dioxo-2-oxa-11,14-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3⁽²²⁾,4,6,17⁽²¹⁾,18-hexaene-15-carboxylic acid methyl ester

Base Information

• Chemical Name: (9S,12S,15S)-4-Benzyloxy-9-benzyloxycarbonylamino-12-carbamoylmethyl-10,13-dioxo-2-oxa-11,14-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3⁽²²⁾,4,6,17⁽²¹⁾,18-hexaene-15-carboxylic acid methyl ester
• CAS No.: 127559-32-4
• Molecular Formula: C₃₈H₃₈N₄O₉
• Molecular Weight: 694.741

Synonyms:(9S,12S,15S)-4-Benzyloxy-9-benzyloxycarbonylamino-12-carbamoylmethyl-10,13-dioxo-2-oxa-11,14-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3⁽²²⁾,4,6,17⁽²¹⁾,18-hexaene-15-carboxylic acid methyl ester

Chemical Property of (9S,12S,15S)-4-Benzyloxy-9-benzyloxycarbonylamino-12-carbamoylmethyl-10,13-dioxo-2-oxa-11,14-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3⁽²²⁾,4,6,17⁽²¹⁾,18-hexaene-15-carboxylic acid methyl ester

Chemical Property:

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Technology Process of (9S,12S,15S)-4-Benzyloxy-9-benzyloxycarbonylamino-12-carbamoylmethyl-10,13-dioxo-2-oxa-11,14-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3⁽²²⁾,4,6,17⁽²¹⁾,18-hexaene-15-carboxylic acid methyl ester

There total 14 articles about (9S,12S,15S)-4-Benzyloxy-9-benzyloxycarbonylamino-12-carbamoylmethyl-10,13-dioxo-2-oxa-11,14-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3⁽²²⁾,4,6,17⁽²¹⁾,18-hexaene-15-carboxylic acid methyl 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:

(S)-3-(3-{4-[(S)-2-((S)-2-Amino-3-carbamoyl-propionylamino)-2-methoxycarbonyl-ethyl]-phenoxy}-4-benzyloxy-phenyl)-2-benzyloxycarbonylamino-propionic acid; hydrochloride → (9S,12S,15S)-4-Benzyloxy-9-benzyloxycarbonylamino-12-carbamoylmethyl-10,13-dioxo-2-oxa-11,14-diaza-tricyclo[15.2.2.13,7]docosa-1(20),3(22),4,6,17(21),18-hexaene-15-carboxylic acid methyl ester (127559-32-4)

Guidance literature:

With diphenyl phosphoryl azide; sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 0 ℃; for 72h;

DOI:10.1021/jo00311a019

Reference yield:

(S)-3-(3-{4-[(S)-2-((S)-2-Amino-3-carbamoyl-propionylamino)-2-methoxycarbonyl-ethyl]-phenoxy}-4-benzyloxy-phenyl)-2-benzyloxycarbonylamino-propionic acid (127559-28-8) → (9S,12S,15S)-4-Benzyloxy-9-benzyloxycarbonylamino-12-carbamoylmethyl-10,13-dioxo-2-oxa-11,14-diaza-tricyclo[15.2.2.13,7]docosa-1(20),3(22),4,6,17(21),18-hexaene-15-carboxylic acid methyl ester (127559-32-4)

Guidance literature:

With diphenyl-phosphinic acid; sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 0 ℃;

DOI:10.1016/S0040-4039(01)93447-1

Reference yield:

2-Benzyloxycarbonylamino-3-(4-benzyloxy-3-hydroxy-phenyl)-propionic acid methyl ester (105229-41-2) → (9S,12S,15S)-4-Benzyloxy-9-benzyloxycarbonylamino-12-carbamoylmethyl-10,13-dioxo-2-oxa-11,14-diaza-tricyclo[15.2.2.13,7]docosa-1(20),3(22),4,6,17(21),18-hexaene-15-carboxylic acid methyl ester (127559-32-4)

Guidance literature:

Multi-step reaction with 11 steps

2: 89 percent / BH₃*THF / tetrahydrofuran / 1) 1 h, 0 deg C 2) to 25 deg C, 2 h

3: 92 percent / LiOH*H₂O / tetrahydrofuran; methanol; H₂O / 0.5 h / 25 °C

4: 86 percent / EDCI / CH₂Cl₂ / 12 h / 25 °C

5: 70 percent / CBr₄, Ph₃P / diethyl ether / 12 h / 25 °C

6: 1) NaH / 1) THF, 5-10 min, 25 deg C 2) hexane, THF, 12 h, -78 deg C

7: 0.5N HCl / tetrahydrofuran / 11 h / 25 °C

8: 88 percent / hydroxybenzotriazole, EDCI / dimethylformamide / 12 h / 25 °C

9: 90 percent / n-Bu₄NF / tetrahydrofuran / 4 h / 25 °C

10: 3.0M HCl / ethyl acetate / 0.5 h / 25 °C

11: diphenyl phosphorazidate, NaHCO₃ / dimethylformamide / 72 h / 0 °C

With hydrogenchloride; lithium hydroxide; borane-THF; carbon tetrabromide; diphenyl phosphoryl azide; tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo00311a019

upstream raw materials:

(S)-3-(3-{4-[(S)-2-((S)-2-Amino-3-carbamoyl-propionylamino)-2-methoxycarbonyl-ethyl]-phenoxy}-4-benzyloxy-phenyl)-2-benzyloxycarbonylamino-propionic acid

sodium 4-iodo-benzoate

tert-butyl 4-iodobenzoate

2-Benzyloxycarbonylamino-3-(4-benzyloxy-3-hydroxy-phenyl)-propionic acid methyl ester

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