diethyl (3S,4R)-4-(benzyloxycarbonyloxy)-3-(1-oxohexylamino)undecylphosphonate

Base Information

Chemical Name:diethyl (3S,4R)-4-(benzyloxycarbonyloxy)-3-(1-oxohexylamino)undecylphosphonate
CAS No.:300531-29-7
Molecular Formula:C₂₉H₅₀NO₇P
Molecular Weight:555.692
Hs Code.:

Synonyms:diethyl (3S,4R)-4-(benzyloxycarbonyloxy)-3-(1-oxohexylamino)undecylphosphonate

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Chemical Property of diethyl (3S,4R)-4-(benzyloxycarbonyloxy)-3-(1-oxohexylamino)undecylphosphonate

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Technology Process of diethyl (3S,4R)-4-(benzyloxycarbonyloxy)-3-(1-oxohexylamino)undecylphosphonate

There total 7 articles about diethyl (3S,4R)-4-(benzyloxycarbonyloxy)-3-(1-oxohexylamino)undecylphosphonate 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: 84.5%

: 142-61-0
Hexanoyl chloride

: 300531-28-6
diethyl (3S,4R)-4-(benzyloxycarbonyloxy)-3-(tert-butoxycarbonylamino)undecylphosphonate

: 300531-29-7
diethyl (3S,4R)-4-(benzyloxycarbonyloxy)-3-(1-oxohexylamino)undecylphosphonate

Guidance literature:: diethyl (3S,4R)-4-(benzyloxycarbonyloxy)-3-(tert-butoxycarbonylamino)undecylphosphonate; With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 3h;

With sodium hydroxide; In dichloromethane; chloroform; at 0 ℃; for 0.0833333h;

Hexanoyl chloride; In dichloromethane; chloroform; at 0 ℃; for 0.25h; Further stages.;
DOI:10.1021/jo025529o

Reference yield:

: 300531-26-4
[2-((4S,5R)-5-Heptyl-2-oxo-oxazolidin-4-yl)-ethyl]-phosphonic acid diethyl ester

: 300531-29-7
diethyl (3S,4R)-4-(benzyloxycarbonyloxy)-3-(1-oxohexylamino)undecylphosphonate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 1.96 g / N,N-(dimethylamino)pyridine; Et₃N / dimethylformamide / 0.75 h / 20 °C

2.1: 80.6 percent / cesium carbonate / tetrahydrofuran / 3 h / 20 °C

3.1: CF₃COOH / CH₂Cl₂ / 3 h / 0 °C

3.2: 1N NaOH / CH₂Cl₂; CHCl₃ / 0.08 h / 0 °C

3.3: 84.5 percent / CH₂Cl₂; CHCl₃ / 0.25 h / 0 °C

With dmap; caesium carbonate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo025529o

Reference yield:

: 359828-48-1
(4S,5R)-4-(2-bromoethyl)-5-heptyloxazolidin-2-one

: 300531-29-7
diethyl (3S,4R)-4-(benzyloxycarbonyloxy)-3-(1-oxohexylamino)undecylphosphonate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 3 h / Heating

2.1: 1.96 g / N,N-(dimethylamino)pyridine; Et₃N / dimethylformamide / 0.75 h / 20 °C

3.1: 80.6 percent / cesium carbonate / tetrahydrofuran / 3 h / 20 °C

4.1: CF₃COOH / CH₂Cl₂ / 3 h / 0 °C

4.2: 1N NaOH / CH₂Cl₂; CHCl₃ / 0.08 h / 0 °C

4.3: 84.5 percent / CH₂Cl₂; CHCl₃ / 0.25 h / 0 °C

With dmap; caesium carbonate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo025529o