89872-84-4

Upstream product

• 89889-10-1 Methyl 4,6-O-Benzylidene-3-O-(tert-butyldimethylsilyl)-2-deoxy-2-C-((hydroxymethyl)methylene)-α-D-arabino-hexopyranoside 
• 112711-35-0 methyl 3-O-[(1,1-dimethylethyl)dimethylsilyl]-4,6-O-[(R)-phenylmethylene]-α-D-glucopyranoside 
• 78342-32-2 Methyl 4,6-O-benzylidene-3-O-(t-butyldimethylsilyl)-α-D-ribo-hexopyranosid-2-uloside 
• 78329-22-3 Methyl 4,6-O-Benzylidene-3-O-(tert-butyldimethylsilyl)-2-deoxy-2-C-((E)-carbethoxymethylene)-α-D-arabino-hexopyranoside 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 110889-22-0 Benzoic acid (4aR,6S,8R,8aS)-7-[1-ethoxycarbonyl-meth-(E)-ylidene]-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 

Downstream Products

• 89872-85-5 Methyl 4,6-O-Benzylidene-2-deoxy-2-C-((hydroxymethyl)methylene)-α-D-arabino-hexopyranoside acetonide 
• 89872-85-5 methyl 4,6-O-benzylidene-2-C-<(E)-2-hydroxyethylidene>-3,2¹-O-isopropylidene-α-D-arabino-hexopyranoside 

Relevant academic research and scientific papers

SYTHESIS OF METHYL 4-DEOXY-3-C--α-D-xylo-HEXOPYRANOSIDE AND METHYL 2,21-ANHYDRO-3-C--α-D-GLUCOPYRANOSIDE DERIVATIVES

The title branched-chain sugars possessing a new type of two-carbon branch were synthesised from D-glucose.These compounds are important intermediates for a total synthesis of the nucleoside antibiotics, amipurimycin and miharamycin.

Out-of-Ring Claisen Rearrangement are Highly Stereoselective in Pyranoses: Routes to gem-Dialkylated Sugars

The Claisen rearrangement has been evaluated as a means for stereoselective creation of functionalized geminal substituents at C-2 and C-3 of hexopyrano systems.C-2 and C-3 keto sugars react with Wittig reagents to give α,β-unsaturated esters, one geometric isomer being obtained in each case.Reduction of the ester and trans vinylation with ethyl vinyl ether leads to allyl vinyl ethers wich are thermolysed in refluxing benzonitrile.The oxy-Cope rearrengement proceeds with complete stereoselectivity, the folding pattern being always from the β-face of the pyranose ring.Thus, the acetaldehyde moiety ends up axially oriented at C-2 and equatorially oriented at C-3.These stereochemical results are not affected by neighboring oxygen substituents nor by the presence or absence of an anomeric alkoxyl functionality.