D-myo-Inositol, 1-O-(4-methoxyphenyl)methyl-2,4,6-tris-O-(phenylmethyl)-, 3-(1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo2.2.1heptane-1-carboxylate

Base Information

• Chemical Name: D-myo-Inositol, 1-O-(4-methoxyphenyl)methyl-2,4,6-tris-O-(phenylmethyl)-, 3-(1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo2.2.1heptane-1-carboxylate
• CAS No.: 226889-58-3
• Molecular Formula: C45H50 O10
• Molecular Weight: 750.886
• Mol file: 226889-58-3.mol

Synonyms:D-myo-Inositol, 1-O-(4-methoxyphenyl)methyl-2,4,6-tris-O-(phenylmethyl)-, 3-(1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo2.2.1heptane-1-carboxylate

Chemical Property of D-myo-Inositol, 1-O-(4-methoxyphenyl)methyl-2,4,6-tris-O-(phenylmethyl)-, 3-(1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo2.2.1heptane-1-carboxylate

Chemical Property:

• PSA: 118.98000
• LogP: 6.74480

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-2,4,6-tris-O-(phenylmethyl)-, 3-(1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo2.2.1heptane-1-carboxylate

There total 7 articles about D-myo-Inositol, 1-O-(4-methoxyphenyl)methyl-2,4,6-tris-O-(phenylmethyl)-, 3-(1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo2.2.1heptane-1-carboxylate 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: 49.0%

(1S)-(-)-camphanic chloride (39637-74-6) + 2,4,6-tri-O-benzyl-1-O-(4'-methoxybenzyl)-myo-inositol (211371-78-7) → 1D-2,4,6-tri-O-benzyl-3-O-<(1'S)-camphanoyl>-1-O-(4'-methoxybenzyl)-myo-inositol (226889-58-3,226889-60-7)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1039/b913399b

Reference yield: 24.0%

(1S)-(-)-camphanic chloride (39637-74-6) + 2,4,6-tri-O-benzyl-1-O-(4'-methoxybenzyl)-myo-inositol (211371-78-7) → 1D-2,4,6-tri-O-benzyl-3-O-<(1'S)-camphanoyl>-1-O-(4'-methoxybenzyl)-myo-inositol (226889-58-3,226889-60-7) + 1D-2,4,6-tri-O-benzyl-1-O-<(1'S)-camphanoyl>-3-O-(4'-methoxybenzyl)-myo-inositol (226889-60-7)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 0 ℃; for 24h;

Reference yield:

benzyl bromide (100-39-0) → 1D-2,4,6-tri-O-benzyl-3-O-<(1'S)-camphanoyl>-1-O-(4'-methoxybenzyl)-myo-inositol (226889-58-3,226889-60-7)

Guidance literature:

Multi-step reaction with 5 steps

1: NaH / dimethylformamide / 0 - 20 °C

2: CH₂Cl₂; hexane / 0 - 20 °C

3: 89 percent / NaH, tetrabutylammonium iodide / dimethylformamide / 1.) r.t., 2 h, 2.) r.t., 20 h

4: 92 percent / HCl, H₂O / CHCl₃; methanol / 10 h / 25 °C

5: 24 percent / pyridine, DMAP / CH₂Cl₂ / 24 h / 0 °C

With pyridine; hydrogenchloride; dmap; water; tetra-(n-butyl)ammonium iodide; sodium hydride; In methanol; hexane; dichloromethane; chloroform; N,N-dimethyl-formamide;

upstream raw materials:

(1S)-(-)-camphanic chloride

2,4,6-tri-O-benzyl-1-O-(4'-methoxybenzyl)-myo-inositol

benzyl bromide

(±)-2,4,6-tri-O-benzyl-1,5-O-ethyldiene myo-inositol

Downstream raw materials:

1D-2,4,6-tri-O-benzyl-1-O-(4'-methoxybenzyl)-myo-inositol

(+)-2,3,4,5,6-pentakis-O-benzyl myo-inositol

1D-2,4,6-tri-O-benzyl-myo-inositol 3,5-bis(dibenzyl phosphate)

1D-2,4,6-tri-O-benzyl-1-O-(4'-methoxybenzyl)-myo-inositol 3,5-bis(dibenzyl phosphate)