3,4,3',4'-tetra-O-benzyl-6,6'-O-(o-xylylene)-di-α-D-fructofuranose 1,2':2,1'-dianhydride

Base Information

• Chemical Name: 3,4,3',4'-tetra-O-benzyl-6,6'-O-(o-xylylene)-di-α-D-fructofuranose 1,2':2,1'-dianhydride
• CAS No.: 511544-01-7
• Molecular Formula: C₄₈H₅₀O₁₀
• Molecular Weight: 786.919
• Mol file: 511544-01-7.mol

Synonyms:3,4,3',4'-tetra-O-benzyl-6,6'-O-(o-xylylene)-di-α-D-fructofuranose 1,2':2,1'-dianhydride

Chemical Property of 3,4,3',4'-tetra-O-benzyl-6,6'-O-(o-xylylene)-di-α-D-fructofuranose 1,2':2,1'-dianhydride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4,3',4'-tetra-O-benzyl-6,6'-O-(o-xylylene)-di-α-D-fructofuranose 1,2':2,1'-dianhydride

There total 8 articles about 3,4,3',4'-tetra-O-benzyl-6,6'-O-(o-xylylene)-di-α-D-fructofuranose 1,2':2,1'-dianhydride 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: 79.0%

1,2-bis[(3,4-di-O-benzyl-1,2-O-isopropylidene-β-D-fructofuranose-6-O-yl)methyl]benzene (511544-00-6) → C96H100O20 + 3,4,3',4'-tetra-O-benzyl-6,6'-O-(o-xylylene)-di-β-D-fructofuranose 1,2':2,1'-dianhydride (511544-02-8) + 3,4,3',4'-tetra-O-benzyl-6,6'-O-(o-xylylene)-di-α-D-fructofuranose 1,2':2,1'-dianhydride (511544-01-7)

Guidance literature:

With trifluorormethanesulfonic acid; In dichloromethane; at -78 - 20 ℃;

DOI:10.1021/jo052184b

Reference yield:

1,2-bis[(3,4-di-O-benzyl-1,2-O-isopropylidene-β-D-fructofuranose-6-O-yl)methyl]benzene (511544-00-6) → 3,4,3',4'-tetra-O-benzyl-6,6'-O-(o-xylylene)-di-β-D-fructofuranose 1,2':2,1'-dianhydride (511544-02-8) + 3,4,3',4'-tetra-O-benzyl-6,6'-O-(o-xylylene)-di-α-D-fructofuranose 1,2':2,1'-dianhydride (511544-01-7)

Guidance literature:

With trifluorormethanesulfonic acid; In dichloromethane; at -78 - 20 ℃; for 2h;

DOI:10.1021/ol034022c

Reference yield:

benzyl bromide (100-39-0) → 3,4,3',4'-tetra-O-benzyl-6,6'-O-(o-xylylene)-di-α-D-fructofuranose 1,2':2,1'-dianhydride (511544-01-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / NaH / dimethylformamide / 4 h / 20 °C

2: 90 percent / TBAF / tetrahydrofuran / 3 h / 0 °C

3: 72 percent / NaH / dimethylformamide / 1 h / 20 °C

4: trifluoromethanesulfonic acid / CH₂Cl₂ / 2 h / -78 - 20 °C

With trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol034022c

upstream raw materials:

1,2-bis[(3,4-di-O-benzyl-1,2-O-isopropylidene-β-D-fructofuranose-6-O-yl)methyl]benzene

benzyl bromide

1,2-O-Isopropylidene-β-D-fructofuranose

α,α'-dibromo-o-xylene