2-O-octadecanoyl-1-O-[6-(N-carbobenzyloxyamino)-hexanoyl]-sn-glyceryl-H-phosphonate

Base Information

• Chemical Name: 2-O-octadecanoyl-1-O-[6-(N-carbobenzyloxyamino)-hexanoyl]-sn-glyceryl-H-phosphonate
• CAS No.: 852066-07-0
• Molecular Formula: C₃₅H₆₀NO₉P
• Molecular Weight: 669.836
• Mol file: 852066-07-0.mol

Synonyms:2-O-octadecanoyl-1-O-[6-(N-carbobenzyloxyamino)-hexanoyl]-sn-glyceryl-H-phosphonate

Chemical Property of 2-O-octadecanoyl-1-O-[6-(N-carbobenzyloxyamino)-hexanoyl]-sn-glyceryl-H-phosphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-O-octadecanoyl-1-O-[6-(N-carbobenzyloxyamino)-hexanoyl]-sn-glyceryl-H-phosphonate

There total 3 articles about 2-O-octadecanoyl-1-O-[6-(N-carbobenzyloxyamino)-hexanoyl]-sn-glyceryl-H-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: 92.0%

1-O-[6-(N-carbobenzyloxyamino)-hexanoyl]-2-O-octadecanoyl-sn-glycerol (180894-79-5) → 2-O-octadecanoyl-1-O-[6-(N-carbobenzyloxyamino)-hexanoyl]-sn-glyceryl-H-phosphonate (852066-07-0)

Guidance literature:

With 1H-imidazole; triethylamine; phosphorus trichloride; In toluene; at -5 ℃; for 2h;

DOI:10.1039/b500300h

Reference yield:

6-Benzyloxycarbonylamino-hexanoic acid (S)-2-hydroxy-3-(4-methoxy-benzyloxy)-propyl ester (180894-76-2) → 2-O-octadecanoyl-1-O-[6-(N-carbobenzyloxyamino)-hexanoyl]-sn-glyceryl-H-phosphonate (852066-07-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.5 g / DCC; DMAP / CH₂Cl₂ / 30 °C

2: 93 percent / aq. DDQ / CH₂Cl₂ / 20 °C

3: 92 percent / imidazole; PCl₃; Et₃N / toluene / 2 h / -5 °C

With 1H-imidazole; dmap; triethylamine; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; phosphorus trichloride; In dichloromethane; toluene;

DOI:10.1039/b500300h

Reference yield:

1-O-[6-(N-carbobenzyloxyamino)-hexanoyl]-2-O-octadecanoyl-3-O-(p-methoxybenzyl)-sn-glycerol (180894-78-4) → 2-O-octadecanoyl-1-O-[6-(N-carbobenzyloxyamino)-hexanoyl]-sn-glyceryl-H-phosphonate (852066-07-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / aq. DDQ / CH₂Cl₂ / 20 °C

2: 92 percent / imidazole; PCl₃; Et₃N / toluene / 2 h / -5 °C

With 1H-imidazole; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; phosphorus trichloride; In dichloromethane; toluene;

DOI:10.1039/b500300h

upstream raw materials:

1-O-[6-(N-carbobenzyloxyamino)-hexanoyl]-2-O-octadecanoyl-sn-glycerol

6-Benzyloxycarbonylamino-hexanoic acid (S)-2-hydroxy-3-(4-methoxy-benzyloxy)-propyl ester

1-O-[6-(N-carbobenzyloxyamino)-hexanoyl]-2-O-octadecanoyl-3-O-(p-methoxybenzyl)-sn-glycerol

Downstream raw materials:

(3,4,6-tri-O-benzyl-2-N-(tert-butyloxycarbonyl)-amino-2-deoxy-α-D-glucopyranosyl)-(1-6)-2,3,4,5-tetra-O-benzyl-1-O-(2-octadecanoyl-1-O-[6-(N-carbobenzyloxyamino)-hexanoyl]-sn-glyceryl-phosphonato)-D-myo-inositol

Octadecanoic acid (R)-1-(6-benzyloxycarbonylamino-hexanoyloxymethyl)-2-[hydroxy-((1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentakis-benzyloxy-cyclohexyloxy)-phosphoryloxy]-ethyl ester

Refernces

• 1、 Vishwakarma, Ram A.,Menon, Anant K.. "Flip-flop of glycosylphosphatidylinositols (GPI's) across the ER". . p. 453 - 455. Retrieved 2008/09/18.