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

Base Information

• Chemical Name: 1,2-O-isopropylidene-3-O-(4'-methoxybenzyl)-5-O-(2'-methoxybenzyl)-5-C-vinyl-β-L-ido-pentafuranose
• CAS No.: 741256-75-7
• Molecular Formula: C₂₆H₃₂O₇
• Molecular Weight: 456.536
• Mol file: 741256-75-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about 1,2-O-isopropylidene-3-O-(4'-methoxybenzyl)-5-O-(2'-methoxybenzyl)-5-C-vinyl-β-L-ido-pentafuranose 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: 98.0%

o-Methoxybenzyl chloride (7035-02-1) + 1,2-O-isopropylidene-3-O-(4'-methoxybenzyl)-5-C-vinyl-β-L-ido-pentafuranose (741256-59-7) → 1,2-O-isopropylidene-3-O-(4'-methoxybenzyl)-5-O-(2'-methoxybenzyl)-5-C-vinyl-β-L-ido-pentafuranose (741256-75-7)

Guidance literature:

1,2-O-isopropylidene-3-O-(4'-methoxybenzyl)-5-C-vinyl-β-L-ido-pentafuranose; With sodium hydride; In N,N-dimethyl-formamide; for 2h; ice bath cooling;

o-Methoxybenzyl chloride; 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-isopropylidene-3-O-(4'-methoxybenzyl)-5-O-(2'-methoxybenzyl)-5-C-vinyl-β-L-ido-pentafuranose (741256-75-7)

Guidance literature:

Multi-step reaction with 2 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

With copper(l) iodide; dimethylsulfide; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1248/cpb.52.727

Reference yield: 78.0%

1,2-O-isopropylidene-3-O-(4'-methoxybenzyl)-5-O-(2'-methoxybenzyl)-5-C-vinyl-β-L-ido-pentafuranose (741256-75-7) → 3-O-(4'-methoxybenzyl)-5-O-(2-methoxybenzyl)-5-C-vinyl-L-ido-pentafuranose

Guidance literature:

With sulfuric acid; In tetrahydrofuran; at 60 ℃; for 30h;

DOI:10.1248/cpb.52.727

upstream raw materials:

o-Methoxybenzyl chloride

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

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

Downstream raw materials:

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

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

(3S,4R,5R,6S)-3-(2'-methoxybenzyloxy)-5-(4'-methoxybenzyloxy)-4,6-dihydro-octa-1,7-diene

(+)-3-O-benzoyl-4-O-(4'-methoxybenzyl)-6-O-(2'-methoxybenzyl)-conduritol B