3,4-di-O-benzyl-6-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-β-D-fructofuranose

Base Information

• Chemical Name: 3,4-di-O-benzyl-6-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-β-D-fructofuranose
• CAS No.: 511543-92-3
• Molecular Formula: C₂₉H₄₂O₆Si
• Molecular Weight: 514.734
• Mol file: 511543-92-3.mol

Synonyms:3,4-di-O-benzyl-6-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-β-D-fructofuranose

Chemical Property of 3,4-di-O-benzyl-6-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-β-D-fructofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4-di-O-benzyl-6-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-β-D-fructofuranose

There total 4 articles about 3,4-di-O-benzyl-6-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-β-D-fructofuranose 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: 95.0%

benzyl bromide (100-39-0) + 6-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-β-D-fructofuranose (511543-91-2) → 3,4-di-O-benzyl-6-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-β-D-fructofuranose (511543-92-3)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 5h;

DOI:10.1021/jo052184b

Reference yield:

1,2-O-Isopropylidene-β-D-fructofuranose (76549-76-3) → 3,4-di-O-benzyl-6-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-β-D-fructofuranose (511543-92-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / imidazole / dimethylformamide / 16 h / 20 °C

2: 95 percent / NaH / dimethylformamide / 5 h / 20 °C

With 1H-imidazole; sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1021/jo052184b

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 3,4-di-O-benzyl-6-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-β-D-fructofuranose (511543-92-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / imidazole / dimethylformamide

2: 91 percent / NaH / dimethylformamide / 4 h / 20 °C

With 1H-imidazole; sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1021/ol034022c

upstream raw materials:

benzyl bromide

6-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-β-D-fructofuranose

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

tert-butyldimethylsilyl chloride

Downstream raw materials:

2,3-di-O-benzyl-1,2-O-isopropylidene-β-D-fructofuranose

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

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

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