dimethyl (4S,5R)-5-(benzyloxycarbonyloxy)-4-(1-oxohexylamino)dodecylphosphonate

Base Information

Chemical Name:dimethyl (4S,5R)-5-(benzyloxycarbonyloxy)-4-(1-oxohexylamino)dodecylphosphonate
CAS No.:443793-73-5
Molecular Formula:C₂₈H₄₈NO₇P
Molecular Weight:541.665
Hs Code.:

Synonyms:dimethyl (4S,5R)-5-(benzyloxycarbonyloxy)-4-(1-oxohexylamino)dodecylphosphonate

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Chemical Property of dimethyl (4S,5R)-5-(benzyloxycarbonyloxy)-4-(1-oxohexylamino)dodecylphosphonate

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Technology Process of dimethyl (4S,5R)-5-(benzyloxycarbonyloxy)-4-(1-oxohexylamino)dodecylphosphonate

There total 4 articles about dimethyl (4S,5R)-5-(benzyloxycarbonyloxy)-4-(1-oxohexylamino)dodecylphosphonate 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: 78.8%

: 142-61-0
Hexanoyl chloride

: 443793-75-7
dimethyl (4S,5R)-5-(benzyloxycarbonyloxy)-4-(tert-butoxycarbonylamino)dodecylphosphonate

: 443793-73-5
dimethyl (4S,5R)-5-(benzyloxycarbonyloxy)-4-(1-oxohexylamino)dodecylphosphonate

Guidance literature:: dimethyl (4S,5R)-5-(benzyloxycarbonyloxy)-4-(tert-butoxycarbonylamino)dodecylphosphonate; 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:

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

: 443793-73-5
dimethyl (4S,5R)-5-(benzyloxycarbonyloxy)-4-(1-oxohexylamino)dodecylphosphonate

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

1.2: 62.5 percent / tetrahydrofuran; hexane / 0.33 h / -78 °C

2.1: 56.5 percent / Cs₂CO₃ / tetrahydrofuran / 4 h / 20 °C

3.1: CF₃COOH / CH₂Cl₂ / 3 h / 0 °C

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

3.3: 78.8 percent / CH₂Cl₂; CHCl₃ / 0.25 h / 0 °C

With n-butyllithium; caesium carbonate; trifluoroacetic acid; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/jo025529o

Reference yield:

: 300531-25-3
(4S,5R)-4-(2-hydroxyethyl)-5-heptyloxazolidin-2-one

: 443793-73-5
dimethyl (4S,5R)-5-(benzyloxycarbonyloxy)-4-(1-oxohexylamino)dodecylphosphonate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 100 percent / PPh₃; CBr₄ / CH₂Cl₂ / 0.5 h / 0 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

2.2: 62.5 percent / tetrahydrofuran; hexane / 0.33 h / -78 °C

3.1: 56.5 percent / Cs₂CO₃ / tetrahydrofuran / 4 h / 20 °C

4.1: CF₃COOH / CH₂Cl₂ / 3 h / 0 °C

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

4.3: 78.8 percent / CH₂Cl₂; CHCl₃ / 0.25 h / 0 °C

With n-butyllithium; carbon tetrabromide; caesium carbonate; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/jo025529o