(3S,6S,8R,9S)-N-benzyloxycarbonyl-1,4-diaza-3-benzyl-9-carbomethoxy-5-hydroxy-8-phenyl-2-oxobicylo[4.3.0]nonane

Base Information

Chemical Name:(3S,6S,8R,9S)-N-benzyloxycarbonyl-1,4-diaza-3-benzyl-9-carbomethoxy-5-hydroxy-8-phenyl-2-oxobicylo[4.3.0]nonane
CAS No.:270257-65-3
Molecular Formula:C₃₀H₃₀N₂O₆
Molecular Weight:514.578
Hs Code.:

Synonyms:(3S,6S,8R,9S)-N-benzyloxycarbonyl-1,4-diaza-3-benzyl-9-carbomethoxy-5-hydroxy-8-phenyl-2-oxobicylo[4.3.0]nonane

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Chemical Property of (3S,6S,8R,9S)-N-benzyloxycarbonyl-1,4-diaza-3-benzyl-9-carbomethoxy-5-hydroxy-8-phenyl-2-oxobicylo[4.3.0]nonane

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Technology Process of (3S,6S,8R,9S)-N-benzyloxycarbonyl-1,4-diaza-3-benzyl-9-carbomethoxy-5-hydroxy-8-phenyl-2-oxobicylo[4.3.0]nonane

There total 10 articles about (3S,6S,8R,9S)-N-benzyloxycarbonyl-1,4-diaza-3-benzyl-9-carbomethoxy-5-hydroxy-8-phenyl-2-oxobicylo[4.3.0]nonane 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: 84.0%

: 212612-52-7
(3R,5S)-N-benzyloxycarbonyl-L-phenylalanine-3-phenyl-5-(trans-1-propenyl)-L-proline methyl ester

: 270257-65-3
(3S,6S,8R,9S)-N-benzyloxycarbonyl-1,4-diaza-3-benzyl-9-carbomethoxy-5-hydroxy-8-phenyl-2-oxobicylo[4.3.0]nonane

Guidance literature:: (3R,5S)-N-benzyloxycarbonyl-L-phenylalanine-3-phenyl-5-(trans-1-propenyl)-L-proline methyl ester; With ozone; In methanol; dichloromethane; at -78 ℃; for 0.166667h;

With dimethylsulfide; In methanol; dichloromethane; at -78 - 20 ℃; Further stages.;
DOI:10.1021/jo991649t

Reference yield:

: 212612-51-6
(3R)-N-tert-butyloxycarbonyl-5-methoxy-3-phenyl-L-proline methyl ester

: 270257-65-3
(3S,6S,8R,9S)-N-benzyloxycarbonyl-1,4-diaza-3-benzyl-9-carbomethoxy-5-hydroxy-8-phenyl-2-oxobicylo[4.3.0]nonane

Guidance literature:: Multi-step reaction with 4 steps

1.1: Li / diethyl ether / 2 h / -20 °C

1.2: coppr(I) bromide*Me₂S / diethyl ether / 1 h / -40 °C

1.3: 75 percent / BF₃*Et₂O / diethyl ether / 0.25 h / -78 °C

2.1: BF₃*Et₂O / diethyl ether / 18 h / 20 °C

3.1: cyanuric fluoride; pyridine / CH₂Cl₂ / 1.5 h / -20 °C

3.2: 60 percent / N-ethylmorpholine / CH₂Cl₂ / 18 h / 20 °C

4.1: O₃ / methanol; CH₂Cl₂ / 0.17 h / -78 °C

4.2: 84 percent / Me₂S / methanol; CH₂Cl₂ / -78 - 20 °C

With pyridine; trifluoro-[1,3,5]triazine; boron trifluoride diethyl etherate; lithium; ozone; In methanol; diethyl ether; dichloromethane; 1.1: Metallation / 1.2: Substitution / 1.3: Substitution / 2.1: Substitution / 3.1: Fluorination / 3.2: Acylation / 4.1: Oxidation / 4.2: Cyclization;
DOI:10.1021/jo991649t

Reference yield:

: 212612-60-7
(2S,3R,5S)-3-Phenyl-5-((E)-propenyl)-pyrrolidine-2-carboxylic acid methyl ester

: 270257-65-3
(3S,6S,8R,9S)-N-benzyloxycarbonyl-1,4-diaza-3-benzyl-9-carbomethoxy-5-hydroxy-8-phenyl-2-oxobicylo[4.3.0]nonane

Guidance literature:: Multi-step reaction with 2 steps

1.1: cyanuric fluoride; pyridine / CH₂Cl₂ / 1.5 h / -20 °C

1.2: 60 percent / N-ethylmorpholine / CH₂Cl₂ / 18 h / 20 °C

2.1: O₃ / methanol; CH₂Cl₂ / 0.17 h / -78 °C

2.2: 84 percent / Me₂S / methanol; CH₂Cl₂ / -78 - 20 °C

With pyridine; trifluoro-[1,3,5]triazine; ozone; In methanol; dichloromethane; 1.1: Fluorination / 1.2: Acylation / 2.1: Oxidation / 2.2: Cyclization;
DOI:10.1021/jo991649t