81668-62-4

Basic information

• Product Name: 6,8-di-O-acetyl-3,7-anhydro-2,4,5-trideoxy-1-phenyloct-4-enose
• CAS NO: 81668-62-4
• Molecular Formula: C₁₈H₂₀O₆
• Molecular Weight: 332.3478
• Mol File: 81668-62-4.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 451°C at 760 mmHg
• Flash Point: 197.7°C
• Density: 1.22g/cm³
• Vapor Pressure: 2.51E-08mmHg at 25°C
• Refractive Index: 1.541
• CAS DataBase Reference: 6,8-di-O-acetyl-3,7-anhydro-2,4,5-trideoxy-1-phenyloct-4-enose(CAS DataBase Reference)
• NIST Chemistry Reference: 6,8-di-O-acetyl-3,7-anhydro-2,4,5-trideoxy-1-phenyloct-4-enose(81668-62-4)
• EPA Substance Registry System: 6,8-di-O-acetyl-3,7-anhydro-2,4,5-trideoxy-1-phenyloct-4-enose(81668-62-4)

Safety Data

• Hazardous Substances Data: 81668-62-4(Hazardous Substances Data)

Upstream product

• 13735-81-4 1-styrenyloxytrimethylsilane 
• 74892-46-9 Triacetyl-D-pseudoglucal 
• 2873-29-2 D-glucal triacetate 
• 98-86-2 acetophenone 
• 111425-49-1 phenyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-α-D-erythro-hex-2-enopyranoside 
• 37160-45-5 bis(2-oxo-2-phenyl-ethyl)mercury 
• 52485-06-0 3,4,6-tri-O-acetyl-D-glucal 
• 3323-72-6 ethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside 
• 136787-38-7 styryl 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) 
• 69247-19-4 isopropyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 

Downstream Products

• 81668-63-5 α-(4',6'-Di-O-acetyl-2',3'-dideoxy-α-D-erythro-hex-2'-enopyranosyl)acetophenone 
• 115182-04-2 Acetic acid (2S,6R)-6-(2-oxo-2-phenyl-ethyl)-3,6-dihydro-2H-pyran-2-ylmethyl ester 
• 115182-11-1 Acetic acid (2S,6S)-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.

One-pot Mukaiyama type carbon-Ferrier rearrangement of glycals: Application in the synthesis of chromanone 3-C-glycosides

One-pot carbon-Ferrier rearrangement of glycals with unactivated aryl methyl ketones has been developed under mild Silyl triflate catalysis. Keto methyl group of various aryl methyl ketones without being converted into silyl enol ether could directly attack anomeric position of glycals to form keto functionalized C-glycosides in moderate to good yields with high α-selectivity. The versatility of this method has been extended to the synthesis of a small library of chromanone 3-C-glycosides.

Syntheses and reactions of saturated and 2,3-unsaturated vinyl and 1'-substituted-vinyl glycosides

Reaction of tetra-O-acetyl-α-D-glucopyranosyl bromide with bis(acylmethyl)mercurys [Hg(CH2COR)2] afforded acetylated vinyl [by use of bis(formylmethyl)mercury] or 1'-substituted-vinyl β-D-glucopyranosides 11-13 in high yields. When used together with phenyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-α-D-erythro-hex-2-enopyranoside, these reagents gave analogous vinyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranosides 20-23 which, on treatment with Lewis acids, isomerised to the corresponding C-glycosyl compounds, i.e., (4,6-di-O-acetyl-2,3-dideoxy-D-ertyrho-hex-2-enopyranosyl)acetaldehyd e (24,25) or the corresponding glycosylated methyl ketones 26, 27. A new route to C-3-branched glycals involves treatment of the above thioglycoside or the unsaturated vinyl glycosides with bis(benzoylmethyl)-mercury. Reaction of tetra-O-acetyl-α-D-glucopyranosyl bromide with bis(acylmethyl)mercurys [Hg (CH2COR)2] afforded acetylated vinyl [by use of bis(formylmethyl)mercury] or 1′-substituted-vinyl β-D-glucopyranosides 11-13 in high yields. When used together with phenyl 4 ,6-di-O-acetyl-2,3-dideoxy -1-thio-α-D-erythro -hex-2-enopyranoside, these reagents gave analogous vinyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranosides 20-23 which, on treatment with Lewis acids, isomerised to the corresponding C-glycosyl compounds, i.e., (4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranosyl) acetaldehyde (24,25) or the corresponding glycosylated methyl ketones 26, 27. A new route to C-3-branched glycals involves treatment of the above thioglycoside or the unsaturated vinyl glycosides with bis(benzoylmethyl)-mercury.