D-myo-Inositol, 1-(2R)-2,3-bis(1-oxohexadecyl)oxypropyl hydrogen phosphate 3-(dihydrogen phosphate)

Base Information

• Chemical Name: D-myo-Inositol, 1-(2R)-2,3-bis(1-oxohexadecyl)oxypropyl hydrogen phosphate 3-(dihydrogen phosphate)
• CAS No.: 165689-81-6
• Molecular Formula: C₄₁H₈₀O₁₆P₂
• Molecular Weight: 891.024
• Mol file: 165689-81-6.mol

Synonyms:D-myo-Inositol,1-[2,3-bis[(1-oxohexadecyl)oxy]propyl hydrogen phosphate] 3-(dihydrogenphosphate), (R)-

Chemical Property of D-myo-Inositol, 1-(2R)-2,3-bis(1-oxohexadecyl)oxypropyl hydrogen phosphate 3-(dihydrogen phosphate)

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 921.1°Cat760mmHg
• Flash Point: 510.9°C
• PSA: 275.66000
• Density: 1.21g/cm³
• LogP: 7.84130

Purity/Quality:

≥95% ^*data from raw suppliers

1-2-Dipalmitoyl-sn-glycero-3-phospho-(1?-myoinositol-4?-phosphate) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of D-myo-Inositol, 1-(2R)-2,3-bis(1-oxohexadecyl)oxypropyl hydrogen phosphate 3-(dihydrogen phosphate)

There total 13 articles about D-myo-Inositol, 1-(2R)-2,3-bis(1-oxohexadecyl)oxypropyl hydrogen phosphate 3-(dihydrogen phosphate) 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: 98.0%

(-)-1-O-(1,2-di-O-palmitoyl-sn-glycerol-3-benzyloxyphosphoryl)-2,4,5,6-tetra-O-benzyl-myo-inositol 3-(dibenzyl phosphate) → L-α-phosphatidyl-D-myo-inositol 3-phosphate, dipalmitoyl (165689-81-6,291527-75-8)

Guidance literature:

With hydrogen; palladium; In ethanol; water; for 24h; under 2585.74 Torr;

DOI:10.1021/jo960602u

Reference yield: 95.0%

trimethylsilyl bromide (2857-97-8) + 1D-O-(1,2-dipalmitoyl-sn-glycerol-3-O-methylphospho)-2,3,4,6-O-tetrakis(methoxymethylene)-myo-inositol-5-(dibenzyl phosphate) (496922-03-3) → dipalmitoyl-L-α-phosphatidyl-D-myo-inositol 5-phosphate (165689-81-6,291527-75-8)

Guidance literature:

trimethylsilyl bromide; 1D-O-(1,2-dipalmitoyl-sn-glycerol-3-O-methylphospho)-2,3,4,6-O-tetrakis(methoxymethylene)-myo-inositol-5-(dibenzyl phosphate); at 20 ℃; for 0.5h;

With ethanethiol; In methanol; at 20 ℃; for 1h; Further stages.;

DOI:10.1021/jo0206418

Reference yield: 89.0%

Hexadecanoic acid (R)-2-{benzyloxy-[(1S,2R,3R,4S,5R,6S)-2,3,4,6-tetrakis-benzyloxy-5-(bis-benzyloxy-phosphoryloxy)-cyclohexyloxy]-phosphanyloxy}-1-hexadecanoyloxymethyl-ethyl ester → 1D-1-(1',2'-di-O-hexadecanoyl-sn-glycero(3')phospho)-myo-inositol 3-phosphate (165689-81-6,291527-75-8)

Guidance literature:

With hydrogen; palladium dihydroxide; In tert-butyl alcohol; at 30 ℃; for 48h; under 3102.89 Torr;

upstream raw materials:

1D-O-(1,2-di-O-palmitoyl-sn-glycerol-3-O-methylphospho)-2,4,5,6-O-tetrakis(methoxymethylene)-myo-inositol 3-(dibenzyl phosphate)

trimethylsilyl bromide

1D-O-(1,2-dipalmitoyl-sn-glycerol-3-O-methylphospho)-2,3,4,6-O-tetrakis(methoxymethylene)-myo-inositol-5-(dibenzyl phosphate)

Hexadecanoic acid (R)-2-(diisopropylamino-methoxy-phosphanyloxy)-1-hexadecanoyloxymethyl-ethyl ester

Refernces

• 1、 Conway, Stuart J.,Gardiner, James,Grove, Simon J. A.,Johns, Melloney K.,Lim, Ze-Yi,Painter, Gavin F.,Robinson, Diane E. J. E.,Schieber, Christine,Thuring, Jan W.,Wong, Leon S.-M.,Yin, Meng-Xin,Burgess, Antony W.,Catimel, Bruno,Hawkins, Phillip T.,Ktistakis, Nicholas T.,Stephens, Leonard R.,Holmes, Andrew B.. "Synthesis and biological evaluation of phosphatidylinositol phosphate affinity probes". scheme or table. p. 66 - 76. Retrieved 2010/04/29.
• 2、 Falck,Krishna, U. Murali,Katipally, Kishta Reddy,Capdevila, Jorge H.,Ulug, Emin T.. "Concise syntheses of L-α-phosphatidyl-D-myo-inositol 3-phosphate (3- PIP), 5-phosphate (5-PIP), and 3,5-bisphosphate (3,5-PIP2)". . p. 4271 - 4275. Retrieved 2007/10/03.