(1S,5R,8R)-benzyl 8-hydroxy-3-oxo-2-oxa-6-azabicyclo<3.3.0>octane-6-carboxylate

Base Information

• Chemical Name: (1S,5R,8R)-benzyl 8-hydroxy-3-oxo-2-oxa-6-azabicyclo<3.3.0>octane-6-carboxylate
• CAS No.: 95456-64-7
• Molecular Formula: C₁₄H₁₅NO₅
• Molecular Weight: 277.277
• Mol file: 95456-64-7.mol

Synonyms:(1S,5R,8R)-benzyl 8-hydroxy-3-oxo-2-oxa-6-azabicyclo<3.3.0>octane-6-carboxylate

Chemical Property of (1S,5R,8R)-benzyl 8-hydroxy-3-oxo-2-oxa-6-azabicyclo<3.3.0>octane-6-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,5R,8R)-benzyl 8-hydroxy-3-oxo-2-oxa-6-azabicyclo<3.3.0>octane-6-carboxylate

There total 10 articles about (1S,5R,8R)-benzyl 8-hydroxy-3-oxo-2-oxa-6-azabicyclo<3.3.0>octane-6-carboxylate 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: 83.0%

carbon monoxide (201230-82-2) + (2R,3S)-1-benzyloxycarbonylamino-4-pentene-2,3-diol (129570-51-0) → (1S,5R,8R)-benzyl 8-hydroxy-3-oxo-2-oxa-6-azabicyclo<3.3.0>octane-6-carboxylate (95456-64-7)

Guidance literature:

With sodium acetate; copper dichloride; palladium dichloride; In acetic acid; at 25 ℃; 2-4d;

Reference yield: 82.0%

(2R,3S,4R)-methyl (1-benzyloxycarbonyl-3,4-isopropylidenedioxypyrrolidin-2-yl)acetate (95456-63-6) → (1S,5R,8R)-benzyl 8-hydroxy-3-oxo-2-oxa-6-azabicyclo<3.3.0>octane-6-carboxylate (95456-64-7)

Guidance literature:

With trifluoroacetic acid; for 18h; Ambient temperature;

DOI:10.1039/P19870002377

Reference yield: 50.0%

iron pentacarbonyl (13463-40-6,37220-42-1) + (2R,3S)-1-benzyloxycarbonylamino-4-pentene-2,3-diol (129570-51-0) → (1S,5R,8R)-benzyl 8-hydroxy-3-oxo-2-oxa-6-azabicyclo<3.3.0>octane-6-carboxylate (95456-64-7)

Guidance literature:

With bis(acetonitrile)palladium(II) dichloride; lithium acetate; acetic acid; copper dichloride; In water; at 60 ℃;

DOI:10.1021/acs.joc.9b02453

upstream raw materials:

carbon monoxide

(2R,3S)-1-benzyloxycarbonylamino-4-pentene-2,3-diol

(2R,3S,4R)-methyl (1-benzyloxycarbonyl-3,4-isopropylidenedioxypyrrolidin-2-yl)acetate

(2R,3S,4R)-methyl (3,4-O-isopropylidenedioxypyrrolidin-2-yl)acetate

Downstream raw materials:

1,4,5-trideoxy-1,4-imino-D-lyxo-hexitol

(1R,5R)-(-)-6-aza-6-benzyloxycarbonyl-2-oxabicyclo[3.3.0]octan-3-one

N-benzyloxycarbonyl-1,4,5-trideoxy-1,4-imino-D-lyxo-hexitol

(3aR,6R,6aS)-6-(Imidazole-1-carbothioyloxy)-2-oxo-hexahydro-furo[3,2-b]pyrrole-4-carboxylic acid benzyl ester