(2R,5R,6R,7S)-1-aza-6-((benzyloxy)methyl)-2-(tert-butyl)-6-hydroxy-5-methoxycarbonyl-7-methyl-3-oxa-8-oxobicyclo[3.3.0]-octane

Base Information

Chemical Name:(2R,5R,6R,7S)-1-aza-6-((benzyloxy)methyl)-2-(tert-butyl)-6-hydroxy-5-methoxycarbonyl-7-methyl-3-oxa-8-oxobicyclo[3.3.0]-octane
CAS No.:1373929-15-7
Molecular Formula:C₂₁H₂₉NO₆
Molecular Weight:391.464
Hs Code.:

Synonyms:(2R,5R,6R,7S)-1-aza-6-((benzyloxy)methyl)-2-(tert-butyl)-6-hydroxy-5-methoxycarbonyl-7-methyl-3-oxa-8-oxobicyclo[3.3.0]-octane

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Chemical Property of (2R,5R,6R,7S)-1-aza-6-((benzyloxy)methyl)-2-(tert-butyl)-6-hydroxy-5-methoxycarbonyl-7-methyl-3-oxa-8-oxobicyclo[3.3.0]-octane

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Technology Process of (2R,5R,6R,7S)-1-aza-6-((benzyloxy)methyl)-2-(tert-butyl)-6-hydroxy-5-methoxycarbonyl-7-methyl-3-oxa-8-oxobicyclo[3.3.0]-octane

There total 10 articles about (2R,5R,6R,7S)-1-aza-6-((benzyloxy)methyl)-2-(tert-butyl)-6-hydroxy-5-methoxycarbonyl-7-methyl-3-oxa-8-oxobicyclo[3.3.0]-octane 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: 30.0%

: 1373929-12-4
(2R,5S)-1-(4-(benzyloxy)-2-methyl-3-oxobutanoyl)-2-(tert-butyl)-5-methoxycarbonyl-1,3-oxazolidine

: 1373929-21-5
(2R,5R,6S,7S)-1-aza-6-((benzyloxy)methyl)-2-(tert-butyl)-6-hydroxy-5-methoxycarbonyl-7-methyl-3-oxa-8-oxobicyclo[3.3.0]-octane

: 1373929-18-0
(2R,5R,6S,7R)-1-aza-2-(tert-butyl)-6-hydroxy-7-methyl-6-(benzyloxymethyl)-5-methoxycarbonyl-3-oxa-8-oxobicyclo[3.3.0]octane

: 1373929-15-7
(2R,5R,6R,7S)-1-aza-6-((benzyloxy)methyl)-2-(tert-butyl)-6-hydroxy-5-methoxycarbonyl-7-methyl-3-oxa-8-oxobicyclo[3.3.0]-octane

Guidance literature:: With sodium methylate; In methanol; at 20 ℃; for 24h; diastereoselective reaction;
DOI:10.1039/c2ob00042c

Reference yield:

: 1373929-04-4
(2R,5R,6R)-1-aza-2-(tert-butyl)-6-hydroxy-6-(benzyloxymethyl)-5-methoxycarbonyl-3-oxa-8-oxobicyclo[3.3.0]octane

: 74-88-4
methyl iodide

: 1373929-15-7
(2R,5R,6R,7S)-1-aza-6-((benzyloxy)methyl)-2-(tert-butyl)-6-hydroxy-5-methoxycarbonyl-7-methyl-3-oxa-8-oxobicyclo[3.3.0]-octane

: 1373929-23-7
(2R,5R,6R,7R)-1-aza-2-(tert-butyl)-6-hydroxy-6-(benzyloxymethyl)-5-methoxycarbonyl-7-methyl-3-oxa-8-oxobicyclo[3.3.0]octane

Guidance literature:: (2R,5R,6R)-1-aza-2-(tert-butyl)-6-hydroxy-6-(benzyloxymethyl)-5-methoxycarbonyl-3-oxa-8-oxobicyclo[3.3.0]octane; With lithium diisopropyl amide; In tetrahydrofuran; methanol; at -10 ℃; for 0.5h; Inert atmosphere;

methyl iodide; In tetrahydrofuran; methanol; for 1.5h; diastereoselective reaction; Inert atmosphere;
DOI:10.1039/c2ob00042c

Reference yield:

: 61795-51-5
benzyl 4-(benzyloxy)-3-oxobutanoate

: 1373929-15-7
(2R,5R,6R,7S)-1-aza-6-((benzyloxy)methyl)-2-(tert-butyl)-6-hydroxy-5-methoxycarbonyl-7-methyl-3-oxa-8-oxobicyclo[3.3.0]-octane

Guidance literature:: Multi-step reaction with 4 steps

1.1: water; sodium hydroxide / 30 h / 20 °C

2.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 5.25 h / 0 - 20 °C

3.1: sodium methylate / methanol / 20 °C / Inert atmosphere

4.1: lithium diisopropyl amide / tetrahydrofuran; methanol / 0.5 h / -10 °C / Inert atmosphere

4.2: 1.5 h / Inert atmosphere

With dmap; water; sodium methylate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1039/c2ob00042c