81668-63-5

Basic information

• Product Name: α-(4',6'-Di-O-acetyl-2',3'-dideoxy-α-D-erythro-hex-2'-enopyranosyl)acetophenone
• Synonyms: α-(4',6'-Di-O-acetyl-2',3'-dideoxy-α-D-erythro-hex-2'-enopyranosyl)acetophenone
• CAS NO: 81668-63-5
• Molecular Weight: 332.353
• Mol File: 81668-63-5.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: α-(4',6'-Di-O-acetyl-2',3'-dideoxy-α-D-erythro-hex-2'-enopyranosyl)acetophenone(CAS DataBase Reference)
• NIST Chemistry Reference: α-(4',6'-Di-O-acetyl-2',3'-dideoxy-α-D-erythro-hex-2'-enopyranosyl)acetophenone(81668-63-5)
• EPA Substance Registry System: α-(4',6'-Di-O-acetyl-2',3'-dideoxy-α-D-erythro-hex-2'-enopyranosyl)acetophenone(81668-63-5)

Safety Data

• Hazardous Substances Data: 81668-63-5(Hazardous Substances Data)

Upstream product

• 13735-81-4 1-styrenyloxytrimethylsilane 
• 74892-46-9 Triacetyl-D-pseudoglucal 
• 69247-19-4 isopropyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 
• 65914-22-9 1,4,6-Tri-O-acetyl-α,β-D-erythro-hex-2-enopyranose (Pseudo-C-glucal triacetate) 
• 81668-62-4 α-(4',6'-Di-O-acetyl-2',3'-dideoxy-β-D-erythro-hex-2'-enopyranosyl)acetophenone 
• 136787-38-7 styryl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 
• 3323-72-6 ethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside 
• 2873-29-2 D-glucal triacetate 
• 52485-06-0 3,4,6-tri-O-acetyl-D-glucal 
• 37160-45-5 bis(2-oxo-2-phenyl-ethyl)mercury 
• 111425-49-1 phenyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-α-D-erythro-hex-2-enopyranoside 

Downstream Products

• 115093-67-9 Acetic acid (2S,6S)-6-(2-oxo-2-phenyl-ethyl)-3,6-dihydro-2H-pyran-2-ylmethyl ester 
• 115093-75-9 Acetic acid (2S,6R)-6-(2-oxo-2-phenyl-ethyl)-5,6-dihydro-2H-pyran-2-ylmethyl ester 

Relevant articles and documents

Insight into the Ferrier Rearrangement by Combining Flash Chemistry and Superacids

The transformation of glycals into 2,3-unsaturated glycosyl derivatives, reported by Ferrier in 1962, is supposed to involve an α,β unsaturated glycosyl cation, an elusive ionic species that has still to be observed experimentally. Herein, while combination of TfOH and flow conditions failed to observe this ionic species, its extended lifetime in superacid solutions allowed its characterization by NMR-based structural analysis supported by DFT calculations. This allyloxycarbenium ion was further exploited in the Ferrier rearrangement to afford unsaturated nitrogen-containing C-aryl glycosides and C-alkyl glycosides under superacid and flow conditions, respectively.

Yb(OTf)3-catalyzed C-glycosylation: Highly stereoselective synthesis of C-pseudoglycals

A variety of functionalized C-pseudoglycals (pseudoglycal C-glycosides or C-hex-2-enopyranosides) have been obtained in excellent yields and stereoselectivity from the Yb(OTf)3-catalyzed reaction of tri-O-acetyl glucal with silylated nucleophil

Stereocontrolled Routes to Functionalized C-Glycopyranosides

4,6-O-Ethylidene-D-glucopyranose (1) reacts with an acid-washed, stabilized Wittig reagent to give the trans-oct-2-enoate 2 in excellent yield.Cyclization is effected by treatment with dilute base, and after 1 h, a 1:1 mixture of anomers exists which is the optimum concentration of the α-D form.Continuing base treatment for 5 h leads to the β-D anomer exclusively. α-D-C-Glycopyranosides can be obtained as predominant products by Lewis acid catalyzed condensation of acetylated glycals with siloxyalkenes, and anomerization to the β-D forms can be effected with potassium tert-butoxide.For a given pair of these anomers, 1H or 13C NMR pa rameters can be used for assigning configuration α or β.