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

Base Information

• Chemical Name: 3,5(R)-O-benzylidene-6,7-O-isopropylidene-2-O-trifluoromethanesulphonyl-D-glycero-D-gulo-heptono-1,4-lactone
• CAS No.: 151795-01-6
• Molecular Formula: C₁₈H₁₉F₃O₉S
• Molecular Weight: 468.405
• Mol file: 151795-01-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about 3,5(R)-O-benzylidene-6,7-O-isopropylidene-2-O-trifluoromethanesulphonyl-D-glycero-D-gulo-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: 71.0%

trifluoromethylsulfonic anhydride (358-23-6) + 3,5(R)-O-benzylidene-6,7-O-isopropylidene-D-glycero-D-gulo-heptono-1,4-lactone (151795-00-5) → 3,5(R)-O-benzylidene-6,7-O-isopropylidene-2-O-trifluoromethanesulphonyl-D-glycero-D-gulo-heptono-1,4-lactone (151795-01-6)

Guidance literature:

With pyridine; In dichloromethane; at -30 ℃; for 0.25h;

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(R)-O-benzylidene-6,7-O-isopropylidene-2-O-trifluoromethanesulphonyl-D-glycero-D-gulo-heptono-1,4-lactone (151795-01-6)

Guidance literature:

Multi-step reaction with 5 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

With pyridine; hydrogenchloride; dimethoxypropane; water; sodium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; In dichloromethane; acetone;

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

Reference yield:

benzaldehyde (100-52-7) → 3,5(R)-O-benzylidene-6,7-O-isopropylidene-2-O-trifluoromethanesulphonyl-D-glycero-D-gulo-heptono-1,4-lactone (151795-01-6)

Guidance literature:

Multi-step reaction with 3 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

With pyridine; hydrogenchloride; dimethoxypropane; toluene-4-sulfonic acid; In dichloromethane; acetone;

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

upstream raw materials:

trifluoromethylsulfonic anhydride

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

4,6-O-benzylidene-D-glucose

benzaldehyde

Downstream raw materials:

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

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