2'-(trimethylammonio)-ethyl-4-(hexadecylthio)-3-methoxybutane phosphonate

Base Information

• Chemical Name: 2'-(trimethylammonio)-ethyl-4-(hexadecylthio)-3-methoxybutane phosphonate
• CAS No.: 153413-99-1
• Molecular Formula: C₂₆H₅₆NO₄PS
• Molecular Weight: 509.775
• Mol file: 153413-99-1.mol

Synonyms:2'-(trimethylammonio)-ethyl-4-(hexadecylthio)-3-methoxybutane phosphonate

Chemical Property of 2'-(trimethylammonio)-ethyl-4-(hexadecylthio)-3-methoxybutane phosphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2'-(trimethylammonio)-ethyl-4-(hexadecylthio)-3-methoxybutane phosphonate

There total 10 articles about 2'-(trimethylammonio)-ethyl-4-(hexadecylthio)-3-methoxybutane phosphonate 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:

3-S-hexadecyl-sn-thioglycerol (153483-65-9) → 2'-(trimethylammonio)ethyl 4-(hexadecylthio)-3(S)-methoxybutanephosphonate (153413-99-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 86 percent / triphenylphosphine, diethyl azodicarboxylate / benzene / 24 h / Heating

2: 1.) n-BuLi, 2.) BF₃*Et₂O / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, a) -78 deg C, 3 h, b) -20 deg C, 1 h

3: 88 percent / silica gel / diethyl ether / 30 h / 0 °C

4: 1.) Me₃SiBr, 2.) H₂O / 1.) CH₂Cl₂, RT, 2 h, 2.) THF, RT, 2 h

5: trichloroacetonitrile, pyridine / 48 h

With pyridine; n-butyllithium; trimethylsilyl bromide; boron trifluoride diethyl etherate; water; silica gel; trichloroacetonitrile; triphenylphosphine; diethylazodicarboxylate; In diethyl ether; benzene;

DOI:10.1021/jm00029a016

Reference yield:

1-S-hexadecyl-sn-thioglycerol (152611-24-0) → 2'-(trimethylammonio)ethyl 4-(hexadecylthio)-3(R)-methoxybutanephosphonate (153413-99-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 88 percent / triphenylphosphine, diethyl azodicarboxylate / benzene / 24 h / Heating

2: 1.) n-BuLi, 2.) BF₃*Et₂O / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, a) -78 deg C, 3 h, b) -20 deg C, 1 h

3: 91 percent / silica gel / diethyl ether / 30 h / 0 °C

4: 1.) Me₃SiBr, 2.) H₂O / 1.) CH₂Cl₂, RT, 2 h, 2.) THF, RT, 2 h

5: trichloroacetonitrile, pyridine / 48 h

With pyridine; n-butyllithium; trimethylsilyl bromide; boron trifluoride diethyl etherate; water; silica gel; trichloroacetonitrile; triphenylphosphine; diethylazodicarboxylate; In diethyl ether; benzene;

DOI:10.1021/jm00029a016

Reference yield:

hexadecyl (R)-2-oxiranylmethyl thioether (153414-02-9) → 2'-(trimethylammonio)ethyl 4-(hexadecylthio)-3(R)-methoxybutanephosphonate (153413-99-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) n-BuLi, 2.) BF₃*Et₂O / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, a) -78 deg C, 3 h, b) -20 deg C, 1 h

2: 91 percent / silica gel / diethyl ether / 30 h / 0 °C

3: 1.) Me₃SiBr, 2.) H₂O / 1.) CH₂Cl₂, RT, 2 h, 2.) THF, RT, 2 h

4: trichloroacetonitrile, pyridine / 48 h

With pyridine; n-butyllithium; trimethylsilyl bromide; boron trifluoride diethyl etherate; water; silica gel; trichloroacetonitrile; In diethyl ether;

DOI:10.1021/jm00029a016

upstream raw materials:

choline tosylate

((S)-4-Hexadecylsulfanyl-3-methoxy-butyl)-phosphonic acid

3-S-hexadecyl-sn-thioglycerol

hexadecyl (S)-2-oxiranylmethyl thioether