(4S,5R)-5-(benzyloxycarbonyloxy)-4-(1-oxohexylamino)dodecylphosphonic acid choline monoester

Base Information

Chemical Name:(4S,5R)-5-(benzyloxycarbonyloxy)-4-(1-oxohexylamino)dodecylphosphonic acid choline monoester
CAS No.:443793-76-8
Molecular Formula:C₃₁H₅₅N₂O₇P
Molecular Weight:598.761
Hs Code.:

Synonyms:

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Chemical Property of (4S,5R)-5-(benzyloxycarbonyloxy)-4-(1-oxohexylamino)dodecylphosphonic acid choline monoester

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Technology Process of (4S,5R)-5-(benzyloxycarbonyloxy)-4-(1-oxohexylamino)dodecylphosphonic acid choline monoester

There total 6 articles about (4S,5R)-5-(benzyloxycarbonyloxy)-4-(1-oxohexylamino)dodecylphosphonic acid choline monoester 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:

: 67-48-1
choline chloride

: ((4S,5R)-5-Benzyloxycarbonyloxy-4-hexanoylamino-dodecyl)-phosphonic acid

: ((4S,5R)-5-Benzyloxycarbonyloxy-4-hexanoylamino-dodecyl)-phosphonic acid monovinyl ester

: 443793-76-8
(4S,5R)-5-(benzyloxycarbonyloxy)-4-(1-oxohexylamino)dodecylphosphonic acid choline monoester

Guidance literature:: With trichloroacetonitrile; In pyridine; at 50 ℃; for 40h;
DOI:10.1021/jo025529o

Reference yield:

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

: 443793-76-8
(4S,5R)-5-(benzyloxycarbonyloxy)-4-(1-oxohexylamino)dodecylphosphonic acid choline monoester

Guidance literature:: Multi-step reaction with 6 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

5.1: TMSBr / CH₂Cl₂ / 0.42 h / 20 °C

5.2: methanol / 1 h / 20 °C

6.1: 89 mg / CCl₃CN / pyridine / 40 h / 50 °C

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

Reference yield:

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

: 443793-76-8
(4S,5R)-5-(benzyloxycarbonyloxy)-4-(1-oxohexylamino)dodecylphosphonic acid choline monoester

Guidance literature:: Multi-step reaction with 5 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

4.1: TMSBr / CH₂Cl₂ / 0.42 h / 20 °C

4.2: methanol / 1 h / 20 °C

5.1: 89 mg / CCl₃CN / pyridine / 40 h / 50 °C

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