134877-40-0

Basic information

• Product Name: 3,4-O-BENZYLIDENE-D-RIBO-1,5-LACTONE
• Synonyms: 3,4-O-BENZYLIDENE-D-RIBO-1,5-LACTONE;3,4-O-BENZYLIDENE-D-RIBONO-1,5-LACTONE
• CAS NO: 134877-40-0
• Molecular Formula: C₁₂H₁₂O₅
• Molecular Weight: 236.22
• Mol File: 134877-40-0.mol

Chemical Properties

• Boiling Point: 471.9±45.0 °C(Predicted)
• Appearance: /
• Density: 1.377±0.06 g/cm3(Predicted)
• PKA: 11.95±0.40(Predicted)
• CAS DataBase Reference: 3,4-O-BENZYLIDENE-D-RIBO-1,5-LACTONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-O-BENZYLIDENE-D-RIBO-1,5-LACTONE(134877-40-0)
• EPA Substance Registry System: 3,4-O-BENZYLIDENE-D-RIBO-1,5-LACTONE(134877-40-0)

Safety Data

• Hazardous Substances Data: 134877-40-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3,4-O-Benzylidene-D-ribo-1,5-lactone is used as a precursor in organic synthesis for the preparation of various compounds and pharmaceuticals. Its versatile reactivity allows for the creation of diverse chemical products, making it an essential component in the development of new organic molecules.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 3,4-O-Benzylidene-D-ribo-1,5-lactone is utilized as a key intermediate in the synthesis of medicinal compounds. Its unique structural features and reactivity contribute to the production of innovative drugs with potential therapeutic applications.
Used in Carbohydrate Chemistry Research:
3,4-O-Benzylidene-D-ribo-1,5-lactone serves as a valuable subject in the study of carbohydrate chemistry, providing insights into the properties and reactions of sugar-derived compounds. Its use in research helps advance the understanding of carbohydrate structures and their role in biological systems.
Used as a Chiral Auxiliary in Asymmetric Synthesis:
In the field of asymmetric synthesis, 3,4-O-Benzylidene-D-ribo-1,5-lactone is employed as a chiral auxiliary. Its stereochemistry aids in the selective formation of enantiomerically pure compounds, which is crucial for the development of enantioselective synthetic methods and the production of chiral molecules with specific biological activities.

Upstream product

• 473596-05-3 3,4-O-benzylidene-2-O-tert-butyldimethylsilyl-D-ribono-1,5-lactone 
• 100-52-7 benzaldehyde 
• 5336-08-3 D-Ribono-1,4-lactone 
• 2782-09-4 (4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-dihydro-furan-2-one 

Downstream Products

• 134790-11-7 ((3aR,7R,7aS)-6-Oxo-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl)-carbamic acid benzyl ester 
• 134877-41-1 2-Azido-2-deoxy-3,4-O-benzylidene-1,5-D-ribonolactone 
• 134790-12-8 (5S)-(5-hydroxymethyl-2-oxo-2,5-dihydrofuran-3-yl)carbamic acid benzyl ester 
• 147410-09-1 2-Amino-2-deoxy-3,4-O-benzylidene-1,5-D-ribonolactone 
• 97551-67-2 (3S,5S)-3-benzyloxycarbonylamino-5-hydroxy-γ-lactone 
• 848893-30-1 carbonic acid allyl ester 4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-oxo-tetrahydro-furan-3-yl ester 
• 848893-32-3 3-O-allyl-2-O-tert-butyldimethylsilyl-5-O-tert-butyldiphenylsilyl-D-ribitol 
• 848893-31-2 3-O-allyl-2-O-tert-butyldimethylsilyl-5-O-tert-butyldiphenylsilyl-D-ribono-1,4-lactone 
• 848893-29-8 2-O-tert-butyldimethylsilyl-5-O-tert-butyldiphenylsilyl-D-ribono-1,4-lactone 
• 848893-26-5 3,4-O-benzylidene-1-O-tert-butyldimethylsilyl-D-ribitol 
• 165876-63-1 Acetic acid (3aR,7R,7aR)-6-oxo-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester 
• 138760-69-7 3,4-O-Benzylidene-D-erythro-pentulosono-1,5-lactone hydrate 
• 104945-87-1 Trifluoro-methanesulfonic acid (3aR,7R,7aR)-6-oxo-2-phenyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yl ester 
• 848984-76-9 3,4-O-benzylidene-D-ribitol 

Relevant articles and documents

Synthesis of differentially protected ribitol derivatives from 3,4-O-benzylidene-D-ribono-1,5-lactone

Several differentially protected ribitol derivatives were synthesised using 3,4-O-benzylidene-d-ribono-1,5-lactone as versatile starting compounds for oligosaccharide synthesis. The obtained ribitol derivatives allow the regiospecific coupling of glycosyl

Efficient and chemoselective cleavage of TBS ethers by a sub-stoichiometric amount of decaborane

TBS ethers od aliphatic alcohols in THF-MeOH (or methanol) were deprotected chemoselectively to the corresponding alcohols using a sub-stoichiometric amount of decaborane at rt under nitrogen in high yields.

An efficient and concise entry to (-)-4,5-dihydroxy-d-threo-l norvaline. Formal synthesis of clavalanine

The title amino acid (2) has been synthesized for the first time in a seven-step sequence from D-ribonolactone, in 20% overall yield. Since the N-carbamoyl derivative of (2) in its y-lactone form has been used to prepare clavalanine, a formal total synthe

Synthesis of D-erythroascorbic acid from D-glucose

Reaction of a 4:1 mixture of D-ribono- and D-arabinono-1,4-lactones with benzaldehyde and hydrochloric acid gave 59percent crystalline 3,4-O-benzylidene-D-ribono-1,5-lactone.This acetal was oxidized with manganese dioxide in acetone to its 2-keto-derivative (6) in 76percent yield.Acid-catalyzed methanolysis of 6 gave a syrupy mixture of products, which upon tautomerization in hot methanolic sodium acetate followed by removal of sodium ions gave 78percent D-erythroascorbic acid (7).The overall yield of 7 starting from D-glucose was 20percent.