(3R,4S,5R)-5-benzyloxycarbonyl-5-((S)-((S)-cyclohex-2-enyl)hydroxymethyl)-4-hydroxy-3-(2-hydroxyethyl)-4-methyl-2-pyrrolidone

Base Information

• Chemical Name: (3R,4S,5R)-5-benzyloxycarbonyl-5-((S)-((S)-cyclohex-2-enyl)hydroxymethyl)-4-hydroxy-3-(2-hydroxyethyl)-4-methyl-2-pyrrolidone
• CAS No.: 1309575-70-9
• Molecular Formula: C₂₂H₂₉NO₆
• Molecular Weight: 403.475
• Mol file: 1309575-70-9.mol

Synonyms:(3R,4S,5R)-5-benzyloxycarbonyl-5-((S)-((S)-cyclohex-2-enyl)hydroxymethyl)-4-hydroxy-3-(2-hydroxyethyl)-4-methyl-2-pyrrolidone

Chemical Property of (3R,4S,5R)-5-benzyloxycarbonyl-5-((S)-((S)-cyclohex-2-enyl)hydroxymethyl)-4-hydroxy-3-(2-hydroxyethyl)-4-methyl-2-pyrrolidone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S,5R)-5-benzyloxycarbonyl-5-((S)-((S)-cyclohex-2-enyl)hydroxymethyl)-4-hydroxy-3-(2-hydroxyethyl)-4-methyl-2-pyrrolidone

There total 10 articles about (3R,4S,5R)-5-benzyloxycarbonyl-5-((S)-((S)-cyclohex-2-enyl)hydroxymethyl)-4-hydroxy-3-(2-hydroxyethyl)-4-methyl-2-pyrrolidone 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: 92.3%

(1S,3S,5R,8R)-8-benzyloxycarbonyl-8-((S)-(tert-butoxycarbonyloxy)((S)-cyclohex-2-enyl)methyl)-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one (1309575-69-6) + (1S,3S,5R,8R)-8-benzyloxycarbonyl-7-tert-butoxycarbonyl-8-((S)-((S)-cyclohex-2-enyl)hydroxymethyl)-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one (1309575-68-5) → (3R,4S,5R)-5-benzyloxycarbonyl-5-((S)-((S)-cyclohex-2-enyl)hydroxymethyl)-4-hydroxy-3-(2-hydroxyethyl)-4-methyl-2-pyrrolidone (1309575-70-9)

Guidance literature:

(1S,3S,5R,8R)-8-benzyloxycarbonyl-8-((S)-(tert-butoxycarbonyloxy)((S)-cyclohex-2-enyl)methyl)-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one; (1S,3S,5R,8R)-8-benzyloxycarbonyl-7-tert-butoxycarbonyl-8-((S)-((S)-cyclohex-2-enyl)hydroxymethyl)-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one; With trifluoroacetic acid; In tetrahydrofuran; water; at 0 - 60 ℃; for 2h; Inert atmosphere;

With sodium tetrahydroborate; In tetrahydrofuran; water; toluene; at 0 ℃; for 0.75h; stereoselective reaction; Inert atmosphere;

DOI:10.1021/ol200886j

Reference yield: 89.7%

(1S,3R,5R,8R)-8-benzyloxycarbonyl-8-((S)-(tert-butoxycarbonyloxy)((S)-cyclohex-2-enyl)methyl)-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one (1309575-79-8) + (1S,3R,5R,8R)-8-benzyloxycarbonyl-7-tert-butoxycarbonyl-8-((S)-((S)-cyclohex-2-enyl)(hydroxy)methyl)-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one (1309575-78-7) → (3R,4S,5R)-5-benzyloxycarbonyl-5-((S)-((S)-cyclohex-2-enyl)hydroxymethyl)-4-hydroxy-3-(2-hydroxyethyl)-4-methyl-2-pyrrolidone (1309575-70-9)

Guidance literature:

(1S,3R,5R,8R)-8-benzyloxycarbonyl-8-((S)-(tert-butoxycarbonyloxy)((S)-cyclohex-2-enyl)methyl)-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one; (1S,3R,5R,8R)-8-benzyloxycarbonyl-7-tert-butoxycarbonyl-8-((S)-((S)-cyclohex-2-enyl)(hydroxy)methyl)-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one; With trifluoroacetic acid; In tetrahydrofuran; water; at 0 - 60 ℃; for 3h; Inert atmosphere;

With sodium tetrahydroborate; In tetrahydrofuran; water; toluene; at 0 ℃; for 0.833333h; stereoselective reaction; Inert atmosphere;

DOI:10.1021/ol200886j

Reference yield:

(1S,3S,5R,8S)-8-benzyloxycarbonyl-7-tert-butoxycarbonyl-8-formyl-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one (1309575-76-5) → (3R,4S,5R)-5-benzyloxycarbonyl-5-((S)-((S)-cyclohex-2-enyl)hydroxymethyl)-4-hydroxy-3-(2-hydroxyethyl)-4-methyl-2-pyrrolidone (1309575-70-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium; zinc(II) chloride / tetrahydrofuran; hexane / 5 h / -78 °C / Inert atmosphere

2.1: trifluoroacetic acid / tetrahydrofuran; water / 2 h / 0 - 60 °C / Inert atmosphere

2.2: 0.75 h / 0 °C / Inert atmosphere

With n-butyllithium; trifluoroacetic acid; zinc(II) chloride; In tetrahydrofuran; hexane; water;

DOI:10.1021/ol200886j

upstream raw materials:

(1S,3S,5R)-8,8-dibenzyloxycarbonyl-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one

(1S,3S,5R,8R)-8-benzyloxycarbonyl-8-(hydroxymethyl)-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one

(1S,3S,5R,8R)-8-benzyloxycarbonyl-7-tert-butoxycarbonyl-8-hydroxymethyl-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one

(1S,3S,5R,8S)-8-benzyloxycarbonyl-7-tert-butoxycarbonyl-8-formyl-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one

Downstream raw materials:

NPI-2077

salinosporamide A