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

Base Information

• Chemical Name: 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
• CAS No.: 221004-75-7
• Molecular Formula: C₃₆H₄₅N₃O₅
• Molecular Weight: 599.77

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

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Technology Process of 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

There total 10 articles about 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 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: 73.0%

Acetic acid (3S,4S,7S,11R)-14-amino-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 → 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 (221004-75-7)

Guidance literature:

With copper(I) oxide; phosphoric acid; sodium nitrite; In tetrahydrofuran; water; at 20 ℃; for 1h;

DOI:10.1021/ja0170807

Reference yield:

(2S,3S)-2-Dibenzylamino-3-hydroxy-4-methyl-pentanoic acid pentafluorophenyl ester (221004-70-2) → 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 (221004-75-7)

Guidance literature:

Multi-step reaction with 5 steps

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

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

3: 45 percent / Et₃N; DMAP / CH₂Cl₂ / 5 h / 20 °C

4: SnCl₂*H₂O / dimethylformamide / 5 h / 60 °C

5: 73 percent / H₃PO₄; Cu₂O; NaNO₂ / H₂O; tetrahydrofuran / 1 h / 20 °C

With copper(I) oxide; dmap; phosphoric acid; tetrabutyl ammonium fluoride; triethylamine; tin(ll) chloride; sodium nitrite; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/ja0170807

Reference yield:

(2S,3S)-N,N-dibenzyl hydroxyleucine (202478-35-1) → 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 (221004-75-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 706 mg / EDC / CH₂Cl₂ / 1 h / 20 °C

2: 75 percent / dimethylformamide / 18 h / 20 - 55 °C

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

4: 45 percent / Et₃N; DMAP / CH₂Cl₂ / 5 h / 20 °C

5: SnCl₂*H₂O / dimethylformamide / 5 h / 60 °C

6: 73 percent / H₃PO₄; Cu₂O; NaNO₂ / H₂O; tetrahydrofuran / 1 h / 20 °C

With copper(I) oxide; dmap; phosphoric acid; tetrabutyl ammonium fluoride; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; tin(ll) chloride; sodium nitrite; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/ja0170807

upstream 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

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

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

(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

Downstream raw materials:

sanjoinine G₁

O-Ac-sanjoinine G₁

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