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

Base Information

Chemical Name:tert-butyl (1R,2R,4S,5S,6S)-4-benzamido-5-hydroxy-7-oxabicyclo[4.1.0]heptan-2-ylcarbamate
CAS No.:1620555-86-3
Molecular Formula:C₁₈H₂₄N₂O₅
Molecular Weight:348.399
Hs Code.:

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

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

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

There total 10 articles about tert-butyl (1R,2R,4S,5S,6S)-4-benzamido-5-hydroxy-7-oxabicyclo[4.1.0]heptan-2-ylcarbamate 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: 88.0%

: 1620555-85-2
(1R,2S,5R,6R,Z)-3-(benzoyloxyimino)-5-(tert-butoxycarbonylamino)-7-oxabicyclo[4.1.0]heptan-2-ylbenzoate

: 1620555-86-3
tert-butyl (1R,2R,4S,5S,6S)-4-benzamido-5-hydroxy-7-oxabicyclo[4.1.0]heptan-2-ylcarbamate

Guidance literature:: With sodium tetrahydroborate; nickel(II) chloride hexahydrate; In methanol; at -78 - 20 ℃; for 14h;
DOI:10.1002/chem.201402175

Reference yield:

: 1620555-83-0
(4-hydroxyimino-5-oxo-7-oxabicyclo[4.1.0]hept-2-yl)carbamic acid tert-butyl ester

: 1620555-86-3
tert-butyl (1R,2R,4S,5S,6S)-4-benzamido-5-hydroxy-7-oxabicyclo[4.1.0]heptan-2-ylcarbamate

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: sodium tetrahydroborate; nickel(II) chloride hexahydrate / methanol / 14 h / -78 - 20 °C

With pyridine; sodium tetrahydroborate; nickel(II) chloride hexahydrate; In tetrahydrofuran; methanol;
DOI:10.1002/chem.201402175

Reference yield:

: 1S,4R-4-tert-butoxycarbonylaminocyclohex-2-enyl benzoic acid ester

: 1620555-86-3
tert-butyl (1R,2R,4S,5S,6S)-4-benzamido-5-hydroxy-7-oxabicyclo[4.1.0]heptan-2-ylcarbamate

Guidance literature:: Multi-step reaction with 7 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

7: sodium tetrahydroborate; nickel(II) chloride hexahydrate / methanol / 14 h / -78 - 20 °C

With 4-methyl-morpholine; pyridine; methanol; sodium tetrahydroborate; tetra-n-propylammonium perruthenate.; nickel(II) chloride hexahydrate; potassium tert-butylate; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; isopentyl nitrite; In tetrahydrofuran; methanol; dichloromethane; chloroform;
DOI:10.1002/chem.201402175