(3S,4R)-4-(benzyloxycarbonyloxy)-3-(1-oxohexylamino)undecylphosphonic acid choline monoester

Base Information

Chemical Name:(3S,4R)-4-(benzyloxycarbonyloxy)-3-(1-oxohexylamino)undecylphosphonic acid choline monoester
CAS No.:359828-49-2
Molecular Formula:C₃₀H₅₃N₂O₇P
Molecular Weight:584.734
Hs Code.:

Synonyms:(3S,4R)-4-(benzyloxycarbonyloxy)-3-(1-oxohexylamino)undecylphosphonic acid choline monoester

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Chemical Property of (3S,4R)-4-(benzyloxycarbonyloxy)-3-(1-oxohexylamino)undecylphosphonic acid choline monoester

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Technology Process of (3S,4R)-4-(benzyloxycarbonyloxy)-3-(1-oxohexylamino)undecylphosphonic acid choline monoester

There total 10 articles about (3S,4R)-4-(benzyloxycarbonyloxy)-3-(1-oxohexylamino)undecylphosphonic 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: 16.0%

: 67-48-1
choline chloride

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

: 359828-49-2
(3S,4R)-4-(benzyloxycarbonyloxy)-3-(1-oxohexylamino)undecylphosphonic acid choline monoester

Guidance literature:: diethyl (3S,4R)-4-(benzyloxycarbonyloxy)-3-(1-oxohexylamino)undecylphosphonate; With trimethylsilyl bromide; In dichloromethane;

With water; In tetrahydrofuran; Heating;

choline chloride; With trichloroacetonitrile; In pyridine; at 60 ℃; Further stages.;
DOI:10.1021/ol006147c

Reference yield:

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

: 359828-49-2
(3S,4R)-4-(benzyloxycarbonyloxy)-3-(1-oxohexylamino)undecylphosphonic acid choline monoester

Guidance literature:: Multi-step reaction with 6 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

5.1: Me₃SiBr / CH₂Cl₂ / 3 h / 20 °C

5.2: methanol / 1 h

6.1: 37 mg / CCl₃CN / pyridine / 8 h / 60 °C

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

Reference yield:

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

: 359828-49-2
(3S,4R)-4-(benzyloxycarbonyloxy)-3-(1-oxohexylamino)undecylphosphonic acid choline monoester

Guidance literature:: Multi-step reaction with 5 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

4.1: Me₃SiBr / CH₂Cl₂ / 3 h / 20 °C

4.2: methanol / 1 h

5.1: 37 mg / CCl₃CN / pyridine / 8 h / 60 °C

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