1,2-O-Isopropylidene-3-O-(p-phenylbenzyl)-4,5-O-<(1'R)-trans-3'-phenyl-2'-propen-1'-yl>-β-D-fructopyranose

Base Information

• Chemical Name: 1,2-O-Isopropylidene-3-O-(p-phenylbenzyl)-4,5-O-<(1'R)-trans-3'-phenyl-2'-propen-1'-yl>-β-D-fructopyranose
• CAS No.: 167482-46-4
• Molecular Formula: C₃₁H₃₂O₆
• Molecular Weight: 500.591
• Mol file: 167482-46-4.mol

Synonyms:1,2-O-Isopropylidene-3-O-(p-phenylbenzyl)-4,5-O-<(1'R)-trans-3'-phenyl-2'-propen-1'-yl>-β-D-fructopyranose

Chemical Property of 1,2-O-Isopropylidene-3-O-(p-phenylbenzyl)-4,5-O-<(1'R)-trans-3'-phenyl-2'-propen-1'-yl>-β-D-fructopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2-O-Isopropylidene-3-O-(p-phenylbenzyl)-4,5-O-<(1'R)-trans-3'-phenyl-2'-propen-1'-yl>-β-D-fructopyranose

There total 5 articles about 1,2-O-Isopropylidene-3-O-(p-phenylbenzyl)-4,5-O-<(1'R)-trans-3'-phenyl-2'-propen-1'-yl>-β-D-fructopyranose 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: 35.0%

trans-cinnamaldehyde diethylacetal (25226-98-6) + 1,2-O-Isopropylidene-3-O-(p-phenylbenzyl)-β-D-fructopyranose (167482-35-1) → 1,2-O-Isopropylidene-3-O-(p-phenylbenzyl)-4,5-O-<(1'R)-trans-3'-phenyl-2'-propen-1'-yl>-β-D-fructopyranose (167482-46-4) + 1,2-O-Isopropylidene-3-O-(p-phenylbenzyl)-4,5-O-<(1'S)-trans-3'-phenyl-2'-propen-1'-yl>-β-D-fructopyranose

Guidance literature:

With pyridinium p-toluenesulfonate; In benzene; for 24h; Heating;

DOI:10.1021/jo00108a018

Reference yield:

1,2;4,5-di-O-isopropylidene-β-D-(-)-fructopyranose (25018-67-1) → 1,2-O-Isopropylidene-3-O-(p-phenylbenzyl)-4,5-O-<(1'R)-trans-3'-phenyl-2'-propen-1'-yl>-β-D-fructopyranose (167482-46-4)

Guidance literature:

Multi-step reaction with 3 steps

1: NaH / dimethylformamide / 1.) r.t., 0.5 h, 2.) r.t., 1 h

2: 80percent aq. AcOH / 12 h / Ambient temperature

3: 55 percent / pyridinium tosylate / benzene / 24 h / Heating

With pyridinium p-toluenesulfonate; sodium hydride; acetic acid; In N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo00108a018

Reference yield:

(E)-3-phenylpropenal (14371-10-9) → 1,2-O-Isopropylidene-3-O-(p-phenylbenzyl)-4,5-O-<(1'R)-trans-3'-phenyl-2'-propen-1'-yl>-β-D-fructopyranose (167482-46-4)

Guidance literature:

Multi-step reaction with 2 steps

1: NH₄NO₃ / ethanol / Ambient temperature

2: 55 percent / pyridinium tosylate / benzene / 24 h / Heating

With ammonium nitrate; pyridinium p-toluenesulfonate; In ethanol; benzene;

DOI:10.1021/jo00108a018

upstream raw materials:

trans-cinnamaldehyde diethylacetal

1,2-O-Isopropylidene-3-O-(p-phenylbenzyl)-β-D-fructopyranose

(E)-3-phenylpropenal

1,2;4,5-di-O-isopropylidene-β-D-(-)-fructopyranose

Downstream raw materials:

(1S,2S)-trans-1-(hydroxymethyl)-2-phenylcyclopropane

(1R,2R)-1-hydroxymethyl-2-phenylcyclopropane