146918-99-2

Basic information

• Product Name: 3,4-O-(R)-benzylidene-2-deoxy-D-erythro-ribono-1,5-lactone
• Synonyms: 3,4-O-(R)-benzylidene-2-deoxy-D-erythro-ribono-1,5-lactone
• CAS NO: 146918-99-2
• Molecular Weight: 220.225
• Mol File: 146918-99-2.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 3,4-O-(R)-benzylidene-2-deoxy-D-erythro-ribono-1,5-lactone(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-O-(R)-benzylidene-2-deoxy-D-erythro-ribono-1,5-lactone(146918-99-2)
• EPA Substance Registry System: 3,4-O-(R)-benzylidene-2-deoxy-D-erythro-ribono-1,5-lactone(146918-99-2)

Safety Data

• Hazardous Substances Data: 146918-99-2(Hazardous Substances Data)

Upstream product

• 104945-87-1 3,4-O-(R)-benzylidene-2-O-trifluoromethylsulphonyl-D-ribono-1,5-lactone 
• 102790-69-2 Acetic acid (2R,3aR,7R,7aR)-6-oxo-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester 
• 20603-45-6 3,4-O-Benzylidene-D-(+)-ribonic acid δ-lactone 
• 100-52-7 benzaldehyde 
• 34371-14-7 2-deoxy-D-ribonolactone 
• 452-51-7 D-2-deoxyribose 
• 5336-08-3 D-Ribono-1,4-lactone 

Downstream Products

• 149142-33-6 5-O-trityl-2-deoxy-D-erythro-pentono-1,5-lactone 
• 73968-62-4 (5S)-5-[(trityloxy)methyl]tetrahydro-2-furanone 
• 76236-32-3 2,3-dideoxy-5-O-(triphenylmethyl)-D-glycero-pent-2-enono-1,4-lactone 
• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 
• 34371-14-7 2-deoxy-D-ribonolactone 

Relevant articles and documents

Benzylidene Acetals of the D-Ribonolactones: a Structural Reassessment

The product of the reaction of D-ribono-1,4-lactone with benzaldehyde and concentrated HCl has been shown, by X-ray crystallography of its acetate, to be 3,4-O-(R)-benzylidene-D-ribono-1,5-lactone and not the 3,5-acetal as previously suggested; with ZnCl2 as catalyst the products are 2,3-O-(R)- and -(S)-benzylidene-D-ribono-1,4-lactone, the former preponderating.

Chiral synthesis of (S)-(+)-γ-hydroxymethyl-γ-butyrolactone

S-(+)-γ-hydroxymethyl-γ-butyrolactone has been synthesized from D- ribonolactone as chiral template.

A PRACTICAL SYNTHESIS OF 2-DEOXY ALDONOLACTONES VIA A SmI2-MEDIATED α-DEOXYGENATION REACTION

A one-step deoxygenation of 2-hydroxylactones or their acetates is possible using samarium diiodide as an electron-transfer reagent in conjunction with a proton source.