1-O-tetrahydropyranyl-4,5-O-di(4'-methoxybenzyl)-6-O-(2'-methoxybenzyl)-D-myo-inositol

Base Information

• Chemical Name: 1-O-tetrahydropyranyl-4,5-O-di(4'-methoxybenzyl)-6-O-(2'-methoxybenzyl)-D-myo-inositol
• CAS No.: 741256-72-4
• Molecular Formula: C₃₅H₄₄O₁₀
• Molecular Weight: 624.728
• Mol file: 741256-72-4.mol

Synonyms:1-O-tetrahydropyranyl-4,5-O-di(4'-methoxybenzyl)-6-O-(2'-methoxybenzyl)-D-myo-inositol

Chemical Property of 1-O-tetrahydropyranyl-4,5-O-di(4'-methoxybenzyl)-6-O-(2'-methoxybenzyl)-D-myo-inositol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O-tetrahydropyranyl-4,5-O-di(4'-methoxybenzyl)-6-O-(2'-methoxybenzyl)-D-myo-inositol

There total 10 articles about 1-O-tetrahydropyranyl-4,5-O-di(4'-methoxybenzyl)-6-O-(2'-methoxybenzyl)-D-myo-inositol 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: 75.0%

1-O-tetrahydropyranyl-3-O-benzoyl-4,5-O-di(4'-methoxybenzyl)-6-O-(2'-methoxybenzyl)-D-myo-inositol (741256-71-3) → 1-O-tetrahydropyranyl-4,5-O-di(4'-methoxybenzyl)-6-O-(2'-methoxybenzyl)-D-myo-inositol (741256-72-4)

Guidance literature:

With methanol; potassium carbonate; Heating;

DOI:10.1248/cpb.52.727

Reference yield:

(3aR,5S,6S,6aR)-6-(4-methoxybenzyloxy)-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxole-5-carbaldehyde (82529-87-1) → 1-O-tetrahydropyranyl-4,5-O-di(4'-methoxybenzyl)-6-O-(2'-methoxybenzyl)-D-myo-inositol (741256-72-4)

Guidance literature:

Multi-step reaction with 10 steps

1.1: copper iodide; dimethyl sulfide / tetrahydrofuran / 0.08 h / -40 °C

1.2: 75 percent / CH₂Cl₂ / 3 h / 20 °C

2.1: NaH / dimethylformamide / 2 h / ice bath cooling

2.2: 98 percent / dimethylformamide / 20 °C

3.1: 78 percent / aq. H₂SO₄ / tetrahydrofuran / 30 h / 60 °C

4.1: n-BuLi / diethyl ether / 1.5 h / 20 °C

4.2: 75 percent / diethyl ether; tetrahydrofuran / 20 °C

5.1: 84 percent / benzylidene-bis(tricyclohexylphosphine)-dichlororuthenium / CH₂Cl₂ / 3 h / 20 °C

6.1: 72 percent / 4-dimethylaminopyridine; pyridine / 4 h / 20 °C

7.1: 57 percent / p-TsOH / diethyl ether / 240 h / 20 °C

8.1: 80 percent / quinuclidine; 4-methylmorpholine N-oxide; aq. OsO₄ / CH₂Cl₂ / 48 h / 20 °C

9.1: 72 percent / pyridinium 4-toluenesulfonate / CH₂Cl₂ / 9 h / 20 °C

10.1: 75 percent / K₂CO₃; MeOH / Heating

With Quinuclidine; pyridine; methanol; dmap; copper(l) iodide; osmium(VIII) oxide; Grubbs catalyst first generation; n-butyllithium; dimethylsulfide; sulfuric acid; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.52.727

Reference yield:

1,2-O-isopropylidene-3-O-(4'-methoxybenzyl)-5-C-vinyl-β-L-ido-pentafuranose (741256-59-7) → 1-O-tetrahydropyranyl-4,5-O-di(4'-methoxybenzyl)-6-O-(2'-methoxybenzyl)-D-myo-inositol (741256-72-4)

Guidance literature:

Multi-step reaction with 9 steps

1.1: NaH / dimethylformamide / 2 h / ice bath cooling

1.2: 98 percent / dimethylformamide / 20 °C

2.1: 78 percent / aq. H₂SO₄ / tetrahydrofuran / 30 h / 60 °C

3.1: n-BuLi / diethyl ether / 1.5 h / 20 °C

3.2: 75 percent / diethyl ether; tetrahydrofuran / 20 °C

4.1: 84 percent / benzylidene-bis(tricyclohexylphosphine)-dichlororuthenium / CH₂Cl₂ / 3 h / 20 °C

5.1: 72 percent / 4-dimethylaminopyridine; pyridine / 4 h / 20 °C

6.1: 57 percent / p-TsOH / diethyl ether / 240 h / 20 °C

7.1: 80 percent / quinuclidine; 4-methylmorpholine N-oxide; aq. OsO₄ / CH₂Cl₂ / 48 h / 20 °C

8.1: 72 percent / pyridinium 4-toluenesulfonate / CH₂Cl₂ / 9 h / 20 °C

9.1: 75 percent / K₂CO₃; MeOH / Heating

With Quinuclidine; pyridine; methanol; dmap; osmium(VIII) oxide; Grubbs catalyst first generation; n-butyllithium; sulfuric acid; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.52.727

upstream raw materials:

1-O-tetrahydropyranyl-3-O-benzoyl-4,5-O-di(4'-methoxybenzyl)-6-O-(2'-methoxybenzyl)-D-myo-inositol

(3aR,5S,6S,6aR)-6-(4-methoxybenzyloxy)-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxole-5-carbaldehyde

1,2-O-isopropylidene-3-O-(4'-methoxybenzyl)-5-C-vinyl-β-L-ido-pentafuranose

(+)-3-O-(2'-methoxybenzyl)-5-O-(4'-methoxybenzyl)-conduritol B

Downstream raw materials:

1-O-tetrahydropyranyl-2,3-O-dibenzyl-4,5-O-di(4'-methoxybenzyl)-6-O-(2'-methoxybenzyl)-D-myo-inositol

D-2,3-di-O-benzyl-myo-inositol

2,3-O-dibenzyl-4,5-O-di(4'-methoxybenzyl)-6-O-(2'-methoxybenzyl)-D-myo-inositol