(3S,4S,7S,11R)-4-Dibenzylamino-11-hydroxy-7-isobutyl-3-isopropyl-14-nitro-2-oxa-6,9-diaza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-5,8-dione

Base Information

• Chemical Name: (3S,4S,7S,11R)-4-Dibenzylamino-11-hydroxy-7-isobutyl-3-isopropyl-14-nitro-2-oxa-6,9-diaza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-5,8-dione
• CAS No.: 221004-73-5
• Molecular Formula: C₃₄H₄₂N₄O₆
• Molecular Weight: 602.731

Synonyms:(3S,4S,7S,11R)-4-Dibenzylamino-11-hydroxy-7-isobutyl-3-isopropyl-14-nitro-2-oxa-6,9-diaza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-5,8-dione

Chemical Property of (3S,4S,7S,11R)-4-Dibenzylamino-11-hydroxy-7-isobutyl-3-isopropyl-14-nitro-2-oxa-6,9-diaza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-5,8-dione

Chemical Property:

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Technology Process of (3S,4S,7S,11R)-4-Dibenzylamino-11-hydroxy-7-isobutyl-3-isopropyl-14-nitro-2-oxa-6,9-diaza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-5,8-dione

There total 7 articles about (3S,4S,7S,11R)-4-Dibenzylamino-11-hydroxy-7-isobutyl-3-isopropyl-14-nitro-2-oxa-6,9-diaza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-5,8-dione 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: 45.0%

(2S,3S)-2-Dibenzylamino-3-hydroxy-4-methyl-pentanoic acid {(S)-1-[(R)-2-(4-fluoro-3-nitro-phenyl)-2-hydroxy-ethylcarbamoyl]-3-methyl-butyl}-amide (221004-69-9) → (3S,4S,7S,11R)-4-Dibenzylamino-11-hydroxy-7-isobutyl-3-isopropyl-14-nitro-2-oxa-6,9-diaza-bicyclo[10.2.2]hexadeca-1(15),12(16),13-triene-5,8-dione (221004-73-5) + (2S,3S)-2-Dibenzylamino-3-hydroxy-4-methyl-pentanoic acid {(S)-1-[(R)-2-hydroxy-2-(4-hydroxy-3-nitro-phenyl)-ethylcarbamoyl]-3-methyl-butyl}-amide

Guidance literature:

With 3 A molecular sieve; tetrabutyl ammonium fluoride; In dimethyl sulfoxide; at 85 ℃;

DOI:10.1016/S0040-4039(98)80025-7

Reference yield:

(2S,3S)-2-Dibenzylamino-3-hydroxy-4-methyl-pentanoic acid {(S)-1-[(R)-2-(4-fluoro-3-nitro-phenyl)-2-hydroxy-ethylcarbamoyl]-3-methyl-butyl}-amide (221004-69-9) → (3S,4S,7S,11R)-4-Dibenzylamino-11-hydroxy-7-isobutyl-3-isopropyl-14-nitro-2-oxa-6,9-diaza-bicyclo[10.2.2]hexadeca-1(15),12(16),13-triene-5,8-dione (221004-73-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; dimethyl sulfoxide; at 85 ℃; for 4h;

DOI:10.1021/ja0170807

Reference yield:

(2S,3S)-2-Dibenzylamino-3-hydroxy-4-methyl-pentanoic acid pentafluorophenyl ester (221004-70-2) → (3S,4S,7S,11R)-4-Dibenzylamino-11-hydroxy-7-isobutyl-3-isopropyl-14-nitro-2-oxa-6,9-diaza-bicyclo[10.2.2]hexadeca-1(15),12(16),13-triene-5,8-dione (221004-73-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / dimethylformamide / 18 h / 20 - 55 °C

2: TBAF; MS 3A / dimethylsulfoxide; tetrahydrofuran / 4 h / 85 °C

With tetrabutyl ammonium fluoride; In tetrahydrofuran; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/ja0170807

upstream raw materials:

(2S,3S)-2-Dibenzylamino-3-hydroxy-4-methyl-pentanoic acid {(S)-1-[(R)-2-(4-fluoro-3-nitro-phenyl)-2-hydroxy-ethylcarbamoyl]-3-methyl-butyl}-amide

(2S,3S)-N,N-dibenzyl hydroxyleucine

(2S,3S)-2-Dibenzylamino-3-hydroxy-4-methyl-pentanoic acid pentafluorophenyl ester

(2S,3S)-3-hydroxyleucine

Downstream raw materials:

Acetic acid (3S,4S,7S,11R)-4-dibenzylamino-7-isobutyl-3-isopropyl-14-nitro-5,8-dioxo-2-oxa-6,9-diaza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-trien-11-yl ester

sanjoinine G₁

O-Ac-sanjoinine G₁

Acetic acid (3S,4S,7S,11R)-4-dibenzylamino-7-isobutyl-3-isopropyl-5,8-dioxo-2-oxa-6,9-diaza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-trien-11-yl ester

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