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

Base Information

• Chemical Name: 1,2-O-dibenzyl-3,4,5,6-O-tetra-(4'-methoxybenzyl)-D-myo-inositol
• CAS No.: 741256-65-5
• Molecular Formula: C₅₂H₅₆O₁₀
• Molecular Weight: 841.011
• Mol file: 741256-65-5.mol

Synonyms:1,2-O-dibenzyl-3,4,5,6-O-tetra-(4'-methoxybenzyl)-D-myo-inositol

Chemical Property of 1,2-O-dibenzyl-3,4,5,6-O-tetra-(4'-methoxybenzyl)-D-myo-inositol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2-O-dibenzyl-3,4,5,6-O-tetra-(4'-methoxybenzyl)-D-myo-inositol

There total 7 articles about 1,2-O-dibenzyl-3,4,5,6-O-tetra-(4'-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: 93.0%

benzyl bromide (100-39-0) + 3,4,5,6-O-tetra-(4'-methoxybenzyl)-D-myo-inositol (742097-82-1) → 1,2-O-dibenzyl-3,4,5,6-O-tetra-(4'-methoxybenzyl)-D-myo-inositol (741256-65-5)

Guidance literature:

3,4,5,6-O-tetra-(4'-methoxybenzyl)-D-myo-inositol; With sodium hydride; In N,N-dimethyl-formamide; for 2h; ice bath cooling;

benzyl bromide; In N,N-dimethyl-formamide; at 20 ℃;

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) → 1,2-O-dibenzyl-3,4,5,6-O-tetra-(4'-methoxybenzyl)-D-myo-inositol (741256-65-5)

Guidance literature:

Multi-step reaction with 8 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: 50 percent / aq. H₂SO₄ / tetrahydrofuran / 40 h / 40 °C

4.1: n-BuLi / diethyl ether / 2 h / 20 °C

4.2: 70 percent / diethyl ether; tetrahydrofuran / 20 °C

5.1: 87 percent / benzylidene-bis(tricyclohexylphosphine)-dichlororuthenium / CH₂Cl₂ / 3 h / 20 °C

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

6.2: 100 percent / dimethylformamide / 20 °C

7.1: 80 percent / quinuclidine; 4-methylmorpholine N-oxide; aq. OsO₄ / CH₂Cl₂ / 96 h / 20 °C

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

8.2: 93 percent / dimethylformamide / 20 °C

With Quinuclidine; copper(l) iodide; osmium(VIII) oxide; Grubbs catalyst first generation; n-butyllithium; dimethylsulfide; sulfuric acid; sodium hydride; 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) → 1,2-O-dibenzyl-3,4,5,6-O-tetra-(4'-methoxybenzyl)-D-myo-inositol (741256-65-5)

Guidance literature:

Multi-step reaction with 7 steps

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

1.2: 98 percent / dimethylformamide / 20 °C

2.1: 50 percent / aq. H₂SO₄ / tetrahydrofuran / 40 h / 40 °C

3.1: n-BuLi / diethyl ether / 2 h / 20 °C

3.2: 70 percent / diethyl ether; tetrahydrofuran / 20 °C

4.1: 87 percent / benzylidene-bis(tricyclohexylphosphine)-dichlororuthenium / CH₂Cl₂ / 3 h / 20 °C

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

5.2: 100 percent / dimethylformamide / 20 °C

6.1: 80 percent / quinuclidine; 4-methylmorpholine N-oxide; aq. OsO₄ / CH₂Cl₂ / 96 h / 20 °C

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

7.2: 93 percent / dimethylformamide / 20 °C

With Quinuclidine; osmium(VIII) oxide; Grubbs catalyst first generation; n-butyllithium; sulfuric acid; sodium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.52.727

upstream raw materials:

benzyl bromide

3,4,5,6-O-tetra-(4'-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

Downstream raw materials:

D-1,2-di-O-benzyl-myo-inositol