D-myo-Inositol, 2,4,5,6-tetrakis-O-(phenylmethyl)-, 3-bis(phenylmethyl) phosphate

Base Information

• Chemical Name: D-myo-Inositol, 2,4,5,6-tetrakis-O-(phenylmethyl)-, 3-bis(phenylmethyl) phosphate
• CAS No.: 180794-84-7
• Molecular Formula: C48H49 O9 P
• Molecular Weight: 800.885
• Mol file: 180794-84-7.mol

Synonyms:D-myo-Inositol, 2,4,5,6-tetrakis-O-(phenylmethyl)-, 3-bis(phenylmethyl) phosphate

Chemical Property of D-myo-Inositol, 2,4,5,6-tetrakis-O-(phenylmethyl)-, 3-bis(phenylmethyl) phosphate

Chemical Property:

• Boiling Point: 858.4±65.0 °C(Predicted)
• PKA: 12.70±0.70(Predicted)
• PSA: 111.72000
• Density: 1.27±0.1 g/cm3(Predicted)
• LogP: 9.62940

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of D-myo-Inositol, 2,4,5,6-tetrakis-O-(phenylmethyl)-, 3-bis(phenylmethyl) phosphate

There total 20 articles about D-myo-Inositol, 2,4,5,6-tetrakis-O-(phenylmethyl)-, 3-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: 95.0%

(-)-2,4,5,6-tetra-O-benzyl-1-O-(p-methoxybenzyl)-myo-inositol 3-(dibenzyl phosphate) (180794-83-6) → (-)-2,4,5,6-tetra-O-benzyl-myo-inositol 3-(dibenzyl phosphate) (180794-84-7)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/jo960602u

Reference yield:

(+)-1,2:5,6-di-O-cyclohexylidene-myo-inositol (41545-19-1) → (-)-2,4,5,6-tetra-O-benzyl-myo-inositol 3-(dibenzyl phosphate) (180794-84-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: di-n-butyltin oxide / toluene / 2 h / Heating

1.2: 88 percent / CsF / dimethylformamide / 17 h / -15 - 20 °C

2.1: NaH / dimethylformamide / 0.5 h / 0 °C

2.2: 97 percent / dimethylformamide / 40 °C

3.1: 82 percent / acetyl chloride; CH₃OH / CH₂Cl₂ / 0.25 h / 23 °C

4.1: NaH / dimethylformamide / 0.5 h / 0 °C

4.2: 97 percent / dimethylformamide / 40 °C

5.1: 92 percent / acetyl chloride; CH₃OH / CH₂Cl₂ / 0.5 h / 23 °C

6.1: di-n-butyltin oxide / toluene / 2 h / Heating

6.2: 95 percent / CsF / dimethylformamide / 17 h / -15 - 20 °C

7.1: NaH / dimethylformamide / 0.5 h / 0 °C

7.2: 96 percent / dimethylformamide / 40 °C

8.1: 88 percent / p-toluenesulfonic acid; water / Pd/C / methanol / 2 h / Heating

9.1: 1H-tetrazole / CH₂Cl₂ / 0.5 h / 23 °C

9.2: CH₂Cl₂ / 12 h / 23 °C

9.3: 93 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 0.5 h / -40 °C

10.1: 95 percent / trifluoroacetic acid / CH₂Cl₂ / 1 h / 20 °C

With 1H-tetrazole; methanol; water; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; acetyl chloride; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: coordination / 1.2: Etherification / 2.1: Metallation / 2.2: Etherification / 3.1: methanolysis / 4.1: Metallation / 4.2: Etherification / 5.1: methanolysis / 6.1: coordination / 6.2: Etherification / 7.1: Metallation / 7.2: Etherification / 8.1: Hydrolysis / 9.1: Addition / 9.2: phosphorylation / 9.3: Oxidation / 10.1: acidolysis;

DOI:10.1021/jo960602u

Reference yield:

(-)-6-O-benzyl-2,3:4,5-di-O-cyclohexylidene-myo-inositol (124601-98-5) → (-)-2,4,5,6-tetra-O-benzyl-myo-inositol 3-(dibenzyl phosphate) (180794-84-7)

Guidance literature:

Multi-step reaction with 9 steps

1.1: NaH / dimethylformamide / 0.5 h / 0 °C

1.2: 97 percent / dimethylformamide / 40 °C

2.1: 82 percent / acetyl chloride; CH₃OH / CH₂Cl₂ / 0.25 h / 23 °C

3.1: NaH / dimethylformamide / 0.5 h / 0 °C

3.2: 97 percent / dimethylformamide / 40 °C

4.1: 92 percent / acetyl chloride; CH₃OH / CH₂Cl₂ / 0.5 h / 23 °C

5.1: di-n-butyltin oxide / toluene / 2 h / Heating

5.2: 95 percent / CsF / dimethylformamide / 17 h / -15 - 20 °C

6.1: NaH / dimethylformamide / 0.5 h / 0 °C

6.2: 96 percent / dimethylformamide / 40 °C

7.1: 88 percent / p-toluenesulfonic acid; water / Pd/C / methanol / 2 h / Heating

8.1: 1H-tetrazole / CH₂Cl₂ / 0.5 h / 23 °C

8.2: CH₂Cl₂ / 12 h / 23 °C

8.3: 93 percent / m-chloroperoxybenzoic acid / CH₂Cl₂ / 0.5 h / -40 °C

9.1: 95 percent / trifluoroacetic acid / CH₂Cl₂ / 1 h / 20 °C

With 1H-tetrazole; methanol; water; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; acetyl chloride; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Metallation / 1.2: Etherification / 2.1: methanolysis / 3.1: Metallation / 3.2: Etherification / 4.1: methanolysis / 5.1: coordination / 5.2: Etherification / 6.1: Metallation / 6.2: Etherification / 7.1: Hydrolysis / 8.1: Addition / 8.2: phosphorylation / 8.3: Oxidation / 9.1: acidolysis;

DOI:10.1021/jo960602u

upstream raw materials:

(-)-2,4,5,6-tetra-O-benzyl-1-O-(p-methoxybenzyl)-myo-inositol 3-(dibenzyl phosphate)

Dibenzyl N,N-diisopropylphosphoramidite

(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:

C₆₉H₇₅NO₁₄P₂