(Z)-(2S,8R)-2-(benzyloxymethyl)-6-(5'-methoxycarbonylpent-4'-en-1'-yl)-8-phenyl-1-aza-9-oxabicyclo[4.3.0]nonane

Base Information

Chemical Name:(Z)-(2S,8R)-2-(benzyloxymethyl)-6-(5'-methoxycarbonylpent-4'-en-1'-yl)-8-phenyl-1-aza-9-oxabicyclo[4.3.0]nonane
CAS No.:1414934-18-1
Molecular Formula:C₂₈H₃₅NO₄
Molecular Weight:449.59
Hs Code.:

Synonyms:(Z)-(2S,8R)-2-(benzyloxymethyl)-6-(5'-methoxycarbonylpent-4'-en-1'-yl)-8-phenyl-1-aza-9-oxabicyclo[4.3.0]nonane

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Chemical Property of (Z)-(2S,8R)-2-(benzyloxymethyl)-6-(5'-methoxycarbonylpent-4'-en-1'-yl)-8-phenyl-1-aza-9-oxabicyclo[4.3.0]nonane

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Technology Process of (Z)-(2S,8R)-2-(benzyloxymethyl)-6-(5'-methoxycarbonylpent-4'-en-1'-yl)-8-phenyl-1-aza-9-oxabicyclo[4.3.0]nonane

There total 6 articles about (Z)-(2S,8R)-2-(benzyloxymethyl)-6-(5'-methoxycarbonylpent-4'-en-1'-yl)-8-phenyl-1-aza-9-oxabicyclo[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: 70.0%

: bis[(2,2,2-trifluoroethyl)methoxycarbonylmethyl]phosphonate

: 233757-75-0
(2S,6R,8R)-2-(benzyloxymethyl)-6-(3'-formyl-1'-propyl)-8-phenyl-1-aza-9-oxabicyclo[4.3.0]nonane

: 1414934-18-1
(Z)-(2S,8R)-2-(benzyloxymethyl)-6-(5'-methoxycarbonylpent-4'-en-1'-yl)-8-phenyl-1-aza-9-oxabicyclo[4.3.0]nonane

Guidance literature:: bis[(2,2,2-trifluoroethyl)methoxycarbonylmethyl]phosphonate; With 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 - 25 ℃; for 0.5h;

(2S,6R,8R)-2-(benzyloxymethyl)-6-(3'-formyl-1'-propyl)-8-phenyl-1-aza-9-oxabicyclo[4.3.0]nonane; In tetrahydrofuran; toluene; at -78 ℃; for 0.833333h;
DOI:10.1039/c2ob26333e DOI:10.1039/c2ob26333e

Reference yield:

: 67-56-1
methanol

: 201230-82-2
carbon monoxide

: 1414934-41-0
(Z)-(2S,8R)-2-(benzyloxymethyl)-6-(5'-iodopent-4'-en-1'-yl)-8-phenyl-1-aza-9-oxabicyclo[4.3.0]nonane

: 1414934-18-1
(Z)-(2S,8R)-2-(benzyloxymethyl)-6-(5'-methoxycarbonylpent-4'-en-1'-yl)-8-phenyl-1-aza-9-oxabicyclo[4.3.0]nonane

: 1414934-36-3
(E)-(2S,8R)-2-(benzyloxymethyl)-6-(5'-methoxycarbonylpent-4'-en-1'-yl)-8-phenyl-1-aza-9-oxabicyclo[4.3.0]nonane

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In acetonitrile; at 60 ℃; Overall yield = 67 %; Overall yield = 7 mg; Darkness;
DOI:10.1039/c2ob26333e DOI:10.1039/c2ob26333e

Reference yield:

: 233757-72-7
(2S,6R,8R)-2-(benzyloxymethyl)-6-[4'-(tert-butyldiphenylsilyloxy)but-1'-yl]-8-phenyl-1-aza-9-oxabicyclo[4.3.0]nonane

: 1414934-18-1
(Z)-(2S,8R)-2-(benzyloxymethyl)-6-(5'-methoxycarbonylpent-4'-en-1'-yl)-8-phenyl-1-aza-9-oxabicyclo[4.3.0]nonane

Guidance literature:: Multi-step reaction with 2 steps

1.1: hydrogen fluoride / acetonitrile

2.1: 18-crown-6 ether; potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -78 - 25 °C

2.2: 0.83 h / -78 °C

With 18-crown-6 ether; hydrogen fluoride; potassium hexamethylsilazane; In tetrahydrofuran; toluene; acetonitrile; 2.1: |Still-Gennary Z-Olefination / 2.2: |Still-Gennary Z-Olefination;
DOI:10.1039/c2ob26333e DOI:10.1039/c2ob26333e