188983-56-4

Upstream product

• 188983-45-1 Benzyloxy-acetic acid (R)-2-benzyloxy-2-[(2R,3S)-3-benzyloxy-4-oxo-1-((R)-1-phenyl-ethyl)-azetidin-2-yl]-ethyl ester 
• 188983-39-3 (R)-2-Benzyloxy-3-[(E)-(R)-1-phenyl-ethylimino]-propan-1-ol 
• 19810-31-2 Benzyloxyacetyl chloride 
• 188983-51-9 (3S,4R)-3-Benzyloxy-4-((R)-1-benzyloxy-2-hydroxy-ethyl)-1-((R)-1-phenyl-ethyl)-azetidin-2-one 

Relevant academic research and scientific papers

Glycono-1,3-lactams, Xylo Series: Stereoselective Access by Cycloaddition, Exploratory Transformations, and Discovery of a New, Highly Selective Inhibitor of Glucoamylases

Cycloaddition of chiral imines 4-7, derived from 2-O-benzylglyceraldehyde, with α-alkoxy ketenes 1-3 furnished 3-amino-3-deoxy-glycono-1,3-lactams 8-15 (50-78 percent) with 2,3-cis configuration in diastereomeric ratios of 87 : 13 to > 95 : 5.From these O,N-deprotected β-lactams 16-18 were prepared.Reduction of the xylono-1,3-lactam 18 using monochloroalane (ClAlH2) produced the corresponding azetidine 19, while reduction of 14 with LiAlH4 gave the aminotetrol derivative 20.Treatment of the β-lactam triol 21 with NaIO4 led to the 3,4-dihydro-2H-1,4-oxazine-3-one 22, via cleavage of the C2-C3 bond and recyclization.The 1,3-imino-xylitol 19 exhibited highly selective inhibition of the two gluco-amylases tested (IC50 values of 31 and 4 (M)).