(1R,4R,5R)-6-(benzyloxycarbonyl)-4-(3-propenyl)-6-aza-2-oxa-bicyclo[3.3.0]-3-octanone

Base Information

Chemical Name:(1R,4R,5R)-6-(benzyloxycarbonyl)-4-(3-propenyl)-6-aza-2-oxa-bicyclo[3.3.0]-3-octanone
CAS No.:328404-64-4
Molecular Formula:C₁₇H₁₉NO₄
Molecular Weight:301.342
Hs Code.:

Synonyms:(1R,4R,5R)-6-(benzyloxycarbonyl)-4-(3-propenyl)-6-aza-2-oxa-bicyclo[3.3.0]-3-octanone

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Chemical Property of (1R,4R,5R)-6-(benzyloxycarbonyl)-4-(3-propenyl)-6-aza-2-oxa-bicyclo[3.3.0]-3-octanone

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Technology Process of (1R,4R,5R)-6-(benzyloxycarbonyl)-4-(3-propenyl)-6-aza-2-oxa-bicyclo[3.3.0]-3-octanone

There total 5 articles about (1R,4R,5R)-6-(benzyloxycarbonyl)-4-(3-propenyl)-6-aza-2-oxa-bicyclo[3.3.0]-3-octanone 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: 57.0%

: 95456-65-8
(1R,5R)-(-)-6-aza-6-benzyloxycarbonyl-2-oxabicyclo[3.3.0]octan-3-one

: 106-95-6
allyl bromide

: 328404-64-4
(1R,4R,5R)-6-(benzyloxycarbonyl)-4-(3-propenyl)-6-aza-2-oxa-bicyclo[3.3.0]-3-octanone

: (1R,5R)-6-(benzyloxycarbonyl)-4-di(3-propenyl)-6-aza-2-oxabicyclo[3.3.0]-3-octanone

Guidance literature:: (1R,5R)-(-)-6-aza-6-benzyloxycarbonyl-2-oxabicyclo[3.3.0]octan-3-one; With lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -78 ℃; for 1h;

allyl bromide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -78 - -45 ℃; for 1.5h; Further stages.;
DOI:10.1021/jo010753j

Reference yield: 57.0%

: 95456-65-8
(1R,5R)-(-)-6-aza-6-benzyloxycarbonyl-2-oxabicyclo[3.3.0]octan-3-one

: 106-95-6
allyl bromide

: 328404-64-4
(1R,4R,5R)-6-(benzyloxycarbonyl)-4-(3-propenyl)-6-aza-2-oxa-bicyclo[3.3.0]-3-octanone

Guidance literature:: With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - -45 ℃; for 0.5h;
DOI:10.1016/S0040-4039(00)01664-6

Reference yield:

: 328404-56-4
(R)-3-[(1-bezyloxy-carbonyl)-pyrrolidinyl]-α-diazoacetate

: 328404-64-4
(1R,4R,5R)-6-(benzyloxycarbonyl)-4-(3-propenyl)-6-aza-2-oxa-bicyclo[3.3.0]-3-octanone

Guidance literature:: Multi-step reaction with 2 steps

1.1: 78 percent / Rh₂[(4R)-1-(3-(PhCH₂CH₂CO)-2-imidazolidinone-4-COOMe)] / 1,2-dichloro-ethane / 2 h / 60 °C

2.1: LiHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / -78 °C

2.2: 57 percent / hexamethylphosphoric acid triamide; tetrahydrofuran / 1.5 h / -78 - -45 °C

With lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dichloro-ethane;
DOI:10.1021/jo010753j