(1S,4S,5R)-4,N-(dibenzyloxycarbonyl)-3-oxa-6-azabicyclo[3.1.0]hexan-2-one

Base Information

• Chemical Name: (1S,4S,5R)-4,N-(dibenzyloxycarbonyl)-3-oxa-6-azabicyclo[3.1.0]hexan-2-one
• CAS No.: 236751-84-1
• Molecular Formula: C₂₀H₁₇NO₆
• Molecular Weight: 367.358
• Mol file: 236751-84-1.mol

Synonyms:(1S,4S,5R)-4,N-(dibenzyloxycarbonyl)-3-oxa-6-azabicyclo[3.1.0]hexan-2-one

Chemical Property of (1S,4S,5R)-4,N-(dibenzyloxycarbonyl)-3-oxa-6-azabicyclo[3.1.0]hexan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4S,5R)-4,N-(dibenzyloxycarbonyl)-3-oxa-6-azabicyclo[3.1.0]hexan-2-one

There total 2 articles about (1S,4S,5R)-4,N-(dibenzyloxycarbonyl)-3-oxa-6-azabicyclo[3.1.0]hexan-2-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: 75.0%

benzyl 2,3-aziridino-N-(benzyloxycarbonyl)-2,3-dideoxy-β-D-lyxofuranuronate (236751-80-7) → (1S,4S,5R)-4,N-(dibenzyloxycarbonyl)-3-oxa-6-azabicyclo[3.1.0]hexan-2-one (236751-84-1)

Guidance literature:

With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; In acetonitrile; for 2.5h;

DOI:10.1016/S0040-4020(99)00405-6

Reference yield:

benzyl [tert-butyldimethylsilyl 2,3-aziridino-N-(benzyloxycarbonyl)-2,3-dideoxy-β-D-lyxofuranosid]uronate (236751-76-1) → (1S,4S,5R)-4,N-(dibenzyloxycarbonyl)-3-oxa-6-azabicyclo[3.1.0]hexan-2-one (236751-84-1)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrabutylammonium fluoride; acetic acid / tetrahydrofuran / 1.33 h / -60 - 20 °C

2: 75 percent / TPAP; 4-methylmorpholine N-oxide / acetonitrile / 2.5 h

With tetrapropylammonium perruthennate; tetrabutyl ammonium fluoride; acetic acid; 4-methylmorpholine N-oxide; In tetrahydrofuran; acetonitrile; 1: Hydrolysis / 2: Oxidation;

DOI:10.1016/S0040-4020(99)00405-6

Reference yield: 44.0%

(1S,4S,5R)-4,N-(dibenzyloxycarbonyl)-3-oxa-6-azabicyclo[3.1.0]hexan-2-one (236751-84-1) → (3S,4S)-DHGA (236751-52-3)

Guidance literature:

(1S,4S,5R)-4,N-(dibenzyloxycarbonyl)-3-oxa-6-azabicyclo[3.1.0]hexan-2-one; With boron trifluoride diethyl etherate; In chloroform; at 0 ℃; for 20h;

With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 2h;

DOI:10.1016/S0040-4020(99)00405-6

upstream raw materials:

benzyl 2,3-aziridino-N-(benzyloxycarbonyl)-2,3-dideoxy-β-D-lyxofuranuronate

benzyl [tert-butyldimethylsilyl 2,3-aziridino-N-(benzyloxycarbonyl)-2,3-dideoxy-β-D-lyxofuranosid]uronate

Downstream raw materials:

(3S,4S)-DHGA