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

Base Information

• Chemical Name: 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
• CAS No.: 852066-08-1
• Molecular Formula: C₇₆H₁₀₀NO₁₅P
• Molecular Weight: 1298.6
• Mol file: 852066-08-1.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 8 articles about 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 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: 57.0%

2-O-octadecanoyl-1-O-[6-(N-carbobenzyloxyamino)-hexanoyl]-sn-glyceryl-H-phosphonate (852066-07-0) + (+)-2,3,4,5,6-pentakis-O-benzyl myo-inositol (6195-45-5,13264-84-1,22132-86-1,25018-91-1,26277-05-4,30694-52-1,28366-79-2) → 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 (852066-08-1)

Guidance literature:

2-O-octadecanoyl-1-O-[6-(N-carbobenzyloxyamino)-hexanoyl]-sn-glyceryl-H-phosphonate; (+)-2,3,4,5,6-pentakis-O-benzyl myo-inositol; With pyridine; pivaloyl chloride; at 20 ℃; for 0.5h;

With pyridine; iodine; at 20 ℃; for 0.416667h;

DOI:10.1039/b500300h

Reference yield:

(+/-)-1-O-allyl-3,4,5,6-tetrakis-O-benzyl myo-inositol (10583-42-3,64681-25-0,64681-27-2,64681-28-3,111466-10-5,111466-15-0,132437-50-4,132437-54-8,135267-01-5,135355-09-8,138923-08-7,138923-09-8,144068-89-3) → 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 (852066-08-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 13 g / NaH / dimethylformamide / 20 °C

2.1: 74 percent / p-TsOH / Pd/C / ethanol / 2 h / Heating

3.1: 36 percent / pyridine / 16 h / 20 °C

4.1: 99 percent / NaOH / methanol / 0.5 h / 60 - 65 °C

5.1: pivaloyl chloride; pyridine / 0.5 h / 20 °C

5.2: 57 percent / I₂; aq. pyridine / 0.42 h / 20 °C

With pyridine; sodium hydroxide; pivaloyl chloride; sodium hydride; toluene-4-sulfonic acid; palladium on activated charcoal; In methanol; ethanol; N,N-dimethyl-formamide;

DOI:10.1039/b500300h

Reference yield:

rac-1,4,5,6-tetra-O-benzyl-myo-inositol (26276-99-3) → 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 (852066-08-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: dibutyltin oxide / toluene / 1 h / Heating

1.2: 12.5 g / dimethylformamide / 4 h / 80 °C

2.1: 13 g / NaH / dimethylformamide / 20 °C

3.1: 74 percent / p-TsOH / Pd/C / ethanol / 2 h / Heating

4.1: 36 percent / pyridine / 16 h / 20 °C

5.1: 99 percent / NaOH / methanol / 0.5 h / 60 - 65 °C

6.1: pivaloyl chloride; pyridine / 0.5 h / 20 °C

6.2: 57 percent / I₂; aq. pyridine / 0.42 h / 20 °C

With pyridine; sodium hydroxide; pivaloyl chloride; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; palladium on activated charcoal; In methanol; ethanol; N,N-dimethyl-formamide; toluene;

DOI:10.1039/b500300h

upstream raw materials:

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

(+)-2,3,4,5,6-pentakis-O-benzyl myo-inositol

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

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

Downstream raw materials:

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

Refernces