27518-97-4

Usage

InChI:InChI=1/C6H12O3/c1-5(8)6(9)3-2-4-7/h4-6,8-9H,2-3H2,1H3/t5-,6+/m1/s1

Upstream product

• 61262-92-8 γ-acetyl-γ-butyrolactone 
• 89195-92-6 (5S,1'R)-4,5-dihydro-5-(1'-hydroxy)ethyl-2-(3H)-furanone 
• 21461-84-7 (2S)-tetrahydro-5-oxofuran-2-carboxylic acid 
• 56-86-0 L-glutamic acid 
• 89158-13-4 (S)-(-)-γ-diazoacetyl-γ-butyrolacetone 
• 54848-33-8 (S)-tetrahydro-5-oxo-2-furancarbonyl chloride 

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

Cytosine-type nucleosides from marine-derived Streptomyces rochei 06CM016

Rocheicoside A (3), a nucleoside analog possessing a novel 5-(hydroxymethyl)-5-methylimidazolidin-4-one substructure, was isolated from marine-derived actinomycete Streptomyces rochei 06CM016, together with a new (4) and three known compounds. Structures of the new metabolites were elucidated by one-dimensional (1H and 13C) and 2D NMR (COSY, HMQC and HMBC) and HR-TOF-MS analyses. All the metabolites exhibited significant antimicrobial activity. A plausible mechanism was proposed for compound 3's formation from amicetin.

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.