(1R,2S,5R,6R,Z)-3-(benzoyloxyimino)-5-(tert-butoxycarbonylamino)-7-oxabicyclo[4.1.0]heptan-2-ylbenzoate

Base Information

• Chemical Name: (1R,2S,5R,6R,Z)-3-(benzoyloxyimino)-5-(tert-butoxycarbonylamino)-7-oxabicyclo[4.1.0]heptan-2-ylbenzoate
• CAS No.: 1620555-85-2
• Molecular Formula: C₂₅H₂₆N₂O₇
• Molecular Weight: 466.491
• Mol file: 1620555-85-2.mol

Synonyms:(1R,2S,5R,6R,Z)-3-(benzoyloxyimino)-5-(tert-butoxycarbonylamino)-7-oxabicyclo[4.1.0]heptan-2-ylbenzoate

Chemical Property of (1R,2S,5R,6R,Z)-3-(benzoyloxyimino)-5-(tert-butoxycarbonylamino)-7-oxabicyclo[4.1.0]heptan-2-ylbenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,5R,6R,Z)-3-(benzoyloxyimino)-5-(tert-butoxycarbonylamino)-7-oxabicyclo[4.1.0]heptan-2-ylbenzoate

There total 9 articles about (1R,2S,5R,6R,Z)-3-(benzoyloxyimino)-5-(tert-butoxycarbonylamino)-7-oxabicyclo[4.1.0]heptan-2-ylbenzoate 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: 70.0%

1S,4R-(5-hydroxy-4-hydroxyimino-7-oxabicyclo[4.1.0]hept-2-yl)carbamic acid tert-butyl ester (1620555-84-1) + benzoyl chloride (98-88-4) → (1R,2S,5R,6R,Z)-3-(benzoyloxyimino)-5-(tert-butoxycarbonylamino)-7-oxabicyclo[4.1.0]heptan-2-ylbenzoate (1620555-85-2)

Guidance literature:

With pyridine; In tetrahydrofuran; at 0 - 20 ℃; for 10h;

DOI:10.1002/chem.201402175

Reference yield:

(4-hydroxyimino-5-oxo-7-oxabicyclo[4.1.0]hept-2-yl)carbamic acid tert-butyl ester (1620555-83-0) → (1R,2S,5R,6R,Z)-3-(benzoyloxyimino)-5-(tert-butoxycarbonylamino)-7-oxabicyclo[4.1.0]heptan-2-ylbenzoate (1620555-85-2)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tetrahydroborate / methanol / 1 h / 0 °C

2: pyridine / tetrahydrofuran / 10 h / 0 - 20 °C

With pyridine; sodium tetrahydroborate; In tetrahydrofuran; methanol;

DOI:10.1002/chem.201402175

Reference yield:

1S,4R-4-tert-butoxycarbonylaminocyclohex-2-enyl benzoic acid ester → (1R,2S,5R,6R,Z)-3-(benzoyloxyimino)-5-(tert-butoxycarbonylamino)-7-oxabicyclo[4.1.0]heptan-2-ylbenzoate (1620555-85-2)

Guidance literature:

Multi-step reaction with 6 steps

1: potassium carbonate; methanol / 4 h / 20 °C

2: 3-chloro-benzenecarboperoxoic acid / chloroform / 24 h / 20 °C

3: 4-methyl-morpholine; tetra-n-propylammonium perruthenate. / dichloromethane / 8 h / 20 °C / Molecular sieve

4: potassium tert-butylate; isopentyl nitrite / tetrahydrofuran / 1 h / -78 °C

5: sodium tetrahydroborate / methanol / 1 h / 0 °C

6: pyridine / tetrahydrofuran / 10 h / 0 - 20 °C

With 4-methyl-morpholine; pyridine; methanol; sodium tetrahydroborate; tetra-n-propylammonium perruthenate.; potassium tert-butylate; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; isopentyl nitrite; In tetrahydrofuran; methanol; dichloromethane; chloroform;

DOI:10.1002/chem.201402175

upstream raw materials:

1S,4R-(5-oxo-7-oxabicyclo[4.1.0]hept-2-yl)carbamic acid tert-butyl ester

1R,4S-(4-hydroxycyclohex-2-enyl)carbamic acid tert-butyl ester

1S,4R-(5-hydroxy-4-hydroxyimino-7-oxabicyclo[4.1.0]hept-2-yl)carbamic acid tert-butyl ester

benzoyl chloride

Downstream raw materials:

(1R,2R,3S,4S,5S)-5-benzamido-2,3,4-trihydroxycyclohexanaminium 2,2,2-trifluoroacetate

tert-butyl (1R,2R,4S,5S,6S)-4-benzamido-5-hydroxy-7-oxabicyclo[4.1.0]heptan-2-ylcarbamate

Refernces