(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

Base Information

• Chemical Name: (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
• CAS No.: 1309575-78-7
• Molecular Formula: C₂₈H₃₇NO₈
• Molecular Weight: 515.604
• Mol file: 1309575-78-7.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 8 articles about (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 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:

(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) + tributyl(cyclohex-2-en-1-yl)stannane (112520-99-7,1177092-71-5) → (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)

Guidance literature:

With n-butyllithium; zinc(II) chloride; In tetrahydrofuran; hexane; at -78 ℃; for 5h; stereoselective reaction; Inert atmosphere;

DOI:10.1021/ol200886j

Reference yield:

(1S,3S,5R,8R)-8-benzyloxycarbonyl-8-(hydroxymethyl)-3-methoxy-1-methyl-2-oxa-7-azabicyclo[3.3.0]octane-6-one (1309575-66-3) → (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)

Guidance literature:

Multi-step reaction with 5 steps

1: acetonitrile / 1 h / 20 °C / Inert atmosphere

2: dmap / acetonitrile / 12 h / 0 °C / Inert atmosphere

3: camphor-10-sulfonic acid / methanol / 3 h / 0 °C / Inert atmosphere

4: Dess-Martin periodane / dichloromethane / 45 h / 20 °C / Inert atmosphere

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

With dmap; n-butyllithium; camphor-10-sulfonic acid; Dess-Martin periodane; zinc(II) chloride; In tetrahydrofuran; methanol; hexane; dichloromethane; acetonitrile;

DOI:10.1021/ol200886j

Reference yield:

C25H37NO8Si → (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)

Guidance literature:

Multi-step reaction with 3 steps

1: camphor-10-sulfonic acid / methanol / 3 h / 0 °C / Inert atmosphere

2: Dess-Martin periodane / dichloromethane / 45 h / 20 °C / Inert atmosphere

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

With n-butyllithium; camphor-10-sulfonic acid; Dess-Martin periodane; zinc(II) chloride; In tetrahydrofuran; methanol; hexane; dichloromethane;

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

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