D-myo-Inositol, 1-O-(4-methoxyphenyl)methyl-2,4,5,6-tetrakis-O-(phenylmethyl)-, bis(phenylmethyl) phosphate

Base Information

• Chemical Name: D-myo-Inositol, 1-O-(4-methoxyphenyl)methyl-2,4,5,6-tetrakis-O-(phenylmethyl)-, bis(phenylmethyl) phosphate
• CAS No.: 180794-83-6
• Molecular Formula: C56H57 O10 P
• Molecular Weight: 921.036
• Mol file: 180794-83-6.mol

Synonyms:D-myo-Inositol, 1-O-(4-methoxyphenyl)methyl-2,4,5,6-tetrakis-O-(phenylmethyl)-, bis(phenylmethyl) phosphate

Chemical Property of D-myo-Inositol, 1-O-(4-methoxyphenyl)methyl-2,4,5,6-tetrakis-O-(phenylmethyl)-, bis(phenylmethyl) phosphate

Chemical Property:

• PSA: 109.95000
• LogP: 11.86250

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of D-myo-Inositol, 1-O-(4-methoxyphenyl)methyl-2,4,5,6-tetrakis-O-(phenylmethyl)-, bis(phenylmethyl) phosphate

There total 35 articles about D-myo-Inositol, 1-O-(4-methoxyphenyl)methyl-2,4,5,6-tetrakis-O-(phenylmethyl)-, bis(phenylmethyl) 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: 93.0%

Dibenzyl N,N-diisopropylphosphoramidite (108549-23-1) + (+)-2,4,5,6-tetra-O-benzyl-1-O-(p-methoxybenzyl)-myo-inositol (141040-56-4) → (-)-2,4,5,6-tetra-O-benzyl-1-O-(p-methoxybenzyl)-myo-inositol 3-(dibenzyl phosphate) (180794-83-6)

Guidance literature:

Dibenzyl N,N-diisopropylphosphoramidite; With 1H-tetrazole; In dichloromethane; at 23 ℃; for 0.5h;

(+)-2,4,5,6-tetra-O-benzyl-1-O-(p-methoxybenzyl)-myo-inositol; In dichloromethane; at 23 ℃; for 12h;

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -40 ℃; for 0.5h;

DOI:10.1021/jo960602u

Reference yield:

Phosphorous acid dibenzyl ester (1R,2S,3R,4R,5S,6S)-2,3,4,6-tetrakis-benzyloxy-5-(4-methoxy-benzyloxy)-cyclohexyl ester → (-)-2,4,5,6-tetra-O-benzyl-1-O-(p-methoxybenzyl)-myo-inositol 3-(dibenzyl phosphate) (180794-83-6)

Guidance literature:

DOI:10.1016/S0008-6215(96)00211-X

Reference yield:

(+)-3-O-allyl-2,4,5,6-tetra-O-benzyl-1-O-(p-methoxybenzyl)-myo-inositol (180794-82-5) → (-)-2,4,5,6-tetra-O-benzyl-1-O-(p-methoxybenzyl)-myo-inositol 3-(dibenzyl phosphate) (180794-83-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 88 percent / p-toluenesulfonic acid; water / Pd/C / methanol / 2 h / Heating

2.1: 1H-tetrazole / CH₂Cl₂ / 0.5 h / 23 °C

2.2: CH₂Cl₂ / 12 h / 23 °C

2.3: 93 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 0.5 h / -40 °C

With 1H-tetrazole; water; toluene-4-sulfonic acid; palladium on activated charcoal; In methanol; dichloromethane; 1.1: Hydrolysis / 2.1: Addition / 2.2: phosphorylation / 2.3: Oxidation;

DOI:10.1021/jo960602u

upstream raw materials:

Dibenzyl N,N-diisopropylphosphoramidite

(+)-2,4,5,6-tetra-O-benzyl-1-O-(p-methoxybenzyl)-myo-inositol

(1R,5S,6R,7S,8S,9S)-6,7,8,9-tetrakis(benzyloxy)-2,4-dioxabicyclo<3.3.1>nonane

(+/-)-2,4,6-tri-O-benzyl-1,3-O-methylidene-D-myo-inositol

Downstream raw materials:

(-)-2,4,5,6-tetra-O-benzyl-myo-inositol 3-(dibenzyl phosphate)

Refernces

• 1、 Painter, Gavin F.,Grove, Simon J. A.,Gilbert, Lan H.,Holmes, Andrew B.,Raithby, Paul R.,Hill, Malcolm L.,Hawking, Phillip T.,Stephens, Leonard R.. "General synthesis of 3-phosphorylated mj'o-inositol phospholipids and derivatives". . p. 923 - 935. Retrieved 2007/10/03.
• 2、 Wang, Da-Sheng,Chen, Ching-Shih. "Synthesis of the D-3 series of phosphatidylinositol phosphates". . p. 5905 - 5910. Retrieved 2007/10/03.