158157-93-8

Upstream product

• 79-37-8 oxalyl dichloride 
• 935-04-6 benzyl vinyl ether 

Downstream Products

• 179924-43-7 methyl trans-4-benzyloxy-2-oxo-3-butenoate 
• 179924-50-6 (R)-1-phenyl-2-(α,α-diphenylbenzyloxy)ethyl-3,4-di-O-benzyl-2-deoxy-6-O-(α,α-diphenylbenzyl)-L-glucoside 
• 179924-49-3 (R)-1-phenyl-2-(α,α-diphenylbenzyloxy)ethyl-3-O-benzyl-2-deoxy-6-O-(α,α-diphenylbenzyl)-L-glucoside 
• 179924-47-1 (2S,3R,4S,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-((R)-2-benzyloxy-1-phenyl-ethoxy)-tetrahydro-pyran 
• 179924-48-2 (R)-2-hydroxy-1-phenylethyl-3-O-benzyl-2-deoxy-L-glucoside 
• 256397-88-3 (1'R,4S,6S)-4-benzyloxy-2,3-dihydro-2-hydroxymethyl-6-(2-hydroxy-1-phenylethoxy)-4H-pyran 
• 207557-97-9 (4S,6S)-4-Benzyloxy-6-((R)-butoxycarbonyl-phenyl-methoxy)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester 
• 154581-21-2 (E)-3-benzyloxypropenoyl chloride 

Relevant academic research and scientific papers

Improved synthesis of (E)-3-alkoxy- and (E)-3-phenoxyacryloyl chlorides

A one-step preparation of (E)-3-alkoxy- and (E)-3-phenoxyacryloyl chlorides by reaction of vinyl ethers and oxalyl chloride with subsequent decarbonylation is presented.

An improved dienophile-induced access to enantiopure 2,4-dideoxysugar lactones via hetero Diels-Alder reaction: Synthesis of the (+)-lactone moiety of compactin

Polystereocontrolled access to 4-type heterocycloadducts was consistently improved by using a new 4-oxy-substituted 1-oxabutadiene, methyl (E)-tert-butoxymethylenepyruvate (1c). Obtained in both enantiomeric forms with high diastereomerical purity, these adducts led to diprotected 2,4- dideoxyglucose 10 and -gluconolactone 12 in both L and D series in high yields. Epimerization of (-)-12 via intramolecular Mitsunobu inversion gave a straightforward access to the lactone moiety (+)-16 of compactin.

Chiral enol ethers in carbohydrate chemistry: De novo synthesis of protected L-2-deoxy hexoses

(3,4,6)Tri- and (3,4)-di-O-benzyl-2-deoxy-L-glucose 8 and 12 have been de novo synthesized in a convergent seven-step sequence involving asymmetric endo heterocycloaddition of the new heterodiene, methyl (E)-benzyloxymethylene pyruvate 2b with the O-vinyl mandelic ester (R)-(-)-3.