35903-48-1

Upstream product

• 61262-92-8 γ-acetyl-γ-butyrolactone 
• 56452-73-4 (S)-5-((S)-1-hydroxyethyl)dihydrofuran-2(3H)-one 
• 258874-00-9 2,3,6-tri-deoxy-4,5-O-isopropylidene-L-threo-hexane aldehyde 
• 56-86-0 L-glutamic acid 
• 54848-33-8 (S)-tetrahydro-5-oxo-2-furancarbonyl chloride 
• 89158-13-4 (S)-(-)-γ-diazoacetyl-γ-butyrolacetone 
• 21461-84-7 (2S)-tetrahydro-5-oxofuran-2-carboxylic acid 
• 439914-97-3 3-[5-(bis-ethylsulfanyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-arcylic acid ethyl ester 
• 439914-98-4 3-(2,2,5-trimethyl-[1,3]dioxolan-4-yl)-propionic acid ethyl ester 

Downstream Products

• 33985-37-4 2,3,6-trideoxy-D-erythrose (2,4-dinitrophenyl)hydrazone 
• 35775-20-3 (4S,5S)-2,3,6-trideoxy-L-threo-hexose(2,4-dinitrophenyl)hydrazone 

Relevant academic research and scientific papers

Efficient Synthesis of the Hexasaccharide Fragment of Landomycin A: Using Phenyl 2,3-O-Thionocarbonyl-1-thioglycosides as 2-Deoxy-β-glycoside Precursors

(Equation Presented) The β-p-methoxyphenol hexadeoxysaccharide fragment of landomycin A was synthesized in a total of 33 steps and 0.5% overall yield starting from D-mannose and D-xylose, featuring the use of phenyl 2,3-O-thionocarbonyl-1-thioglycosides a

SYNTHESIS OF D-AMICETOSE AND L-RHODINOSE FROM L-GLUTAMIC ACID

L-Glutamic acid has been converted into a separable mixture of D-amicetono- and L-rhodinono-γ-lactones by a sequence involving transformation into (S)-γ-carboxy-γ-butyrolactone (2), conversion of 2 into the corresponding methyl ketone by the diazoketone route, and selective reduction with zinc borohydride or boranemethyl sulfide.Reduction of the two lactones with di-isobutylaluminium hydride gave the corresponding deoxy sugars.In spite of some improvements in the preparation of 2, the optical yield of this step was only ca. 80percent, but one crystallisation from chloroform raised the optical purity to 96percent.The subsequent steps produced a loss in optical purity of only 4percent.