dimethyl (4S,5R)-5-(benzyloxycarbonyloxy)-4-(tert-butoxycarbonylamino)dodecylphosphonate

Base Information

Chemical Name:dimethyl (4S,5R)-5-(benzyloxycarbonyloxy)-4-(tert-butoxycarbonylamino)dodecylphosphonate
CAS No.:443793-75-7
Molecular Formula:C₂₇H₄₆NO₈P
Molecular Weight:543.638
Hs Code.:

Synonyms:dimethyl (4S,5R)-5-(benzyloxycarbonyloxy)-4-(tert-butoxycarbonylamino)dodecylphosphonate

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Chemical Property of dimethyl (4S,5R)-5-(benzyloxycarbonyloxy)-4-(tert-butoxycarbonylamino)dodecylphosphonate

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Technology Process of dimethyl (4S,5R)-5-(benzyloxycarbonyloxy)-4-(tert-butoxycarbonylamino)dodecylphosphonate

There total 3 articles about dimethyl (4S,5R)-5-(benzyloxycarbonyloxy)-4-(tert-butoxycarbonylamino)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: 56.5%

: 100-51-6,185532-71-2
benzyl alcohol

: 443793-74-6
dimethyl 3-[(4S,5R)-3-(tert-butyloxycarbonyl)-5-heptyl-2-oxo-oxazolidin-4-yl]propylphosphonate

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

Guidance literature:: With caesium carbonate; In tetrahydrofuran; at 20 ℃; for 4h;
DOI:10.1021/jo025529o

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 2 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

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

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 3 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

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