3,5-O-benzylidene-D-glycero-D-ido-heptono-1,4-lactone

Base Information

• Chemical Name: 3,5-O-benzylidene-D-glycero-D-ido-heptono-1,4-lactone
• CAS No.: 151795-03-8
• Molecular Formula: C₁₄H₁₆O₇
• Molecular Weight: 296.277
• Mol file: 151795-03-8.mol

Synonyms:

Chemical Property of 3,5-O-benzylidene-D-glycero-D-ido-heptono-1,4-lactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,5-O-benzylidene-D-glycero-D-ido-heptono-1,4-lactone

There total 8 articles about 3,5-O-benzylidene-D-glycero-D-ido-heptono-1,4-lactone 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%

3,5-O-benzylidene-6,7-O-isopropylidene-D-glycero-D-ido-heptono-1,4-lactone (151795-02-7) → 3,5-O-benzylidene-D-glycero-D-ido-heptono-1,4-lactone (151795-03-8)

Guidance literature:

With acetic acid; for 22h; Ambient temperature;

DOI:10.1016/S0957-4166(00)80363-8

Reference yield:

4,6-O-benzylidene-D-glucose (3006-41-5,20771-09-9,25152-90-3,97232-16-1,104022-77-7,113566-67-9,113566-68-0) → 3,5-O-benzylidene-D-glycero-D-ido-heptono-1,4-lactone (151795-03-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) NaHCO₃, 2.) H₂O, 3.) AcOH

2: 95 percent / 80percent aq. AcOH / 24 h / Ambient temperature

3: 91 percent / 37percent aq. HCl / 2 h / Ambient temperature

4: 100 percent / p-TsOH*H₂O, dimethoxypropane / acetone / 0.17 h / Ambient temperature

5: 71 percent / pyridine / CH₂Cl₂ / 0.25 h / -30 °C

6: 58 percent / CF₃COONa / dimethylformamide / 72 h / 60 °C

7: 79 percent / 80percent aq. AcOH / 22 h / Ambient temperature

With pyridine; hydrogenchloride; dimethoxypropane; water; sodium 2,2,2-trifluoroacetate; sodium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; In dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0957-4166(00)80363-8

Reference yield:

benzaldehyde (100-52-7) → 3,5-O-benzylidene-D-glycero-D-ido-heptono-1,4-lactone (151795-03-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 91 percent / 37percent aq. HCl / 2 h / Ambient temperature

2: 100 percent / p-TsOH*H₂O, dimethoxypropane / acetone / 0.17 h / Ambient temperature

3: 71 percent / pyridine / CH₂Cl₂ / 0.25 h / -30 °C

4: 58 percent / CF₃COONa / dimethylformamide / 72 h / 60 °C

5: 79 percent / 80percent aq. AcOH / 22 h / Ambient temperature

With pyridine; hydrogenchloride; dimethoxypropane; sodium 2,2,2-trifluoroacetate; toluene-4-sulfonic acid; acetic acid; In dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0957-4166(00)80363-8

upstream raw materials:

3,5-O-benzylidene-6,7-O-isopropylidene-D-glycero-D-ido-heptono-1,4-lactone

4,6-O-benzylidene-D-glucose

benzaldehyde

3,5(R)-O-benzylidene-6,7-O-isopropylidene-2-O-trifluoromethanesulphonyl-D-glycero-D-gulo-heptono-1,4-lactone