191997-66-7

Upstream product

• 186581-53-3 diazomethane 
• 1054651-79-4 (S)-Benzyloxycarbonylamino-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-acetic acid 
• 67-56-1 methanol 
• 213973-69-4 [(R)-1-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-allyl]-carbamic acid benzyl ester 
• 149-73-5 trimethyl orthoformate 
• 1055036-91-3 (R)-2-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-but-3-enoic acid 
• 213973-68-3 (S)-2-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-but-3-en-1-ol 
• 100-51-6 benzyl alcohol 
• 501-53-1 benzyl chloroformate 
• 161614-79-5 (Z)-N-(5-deoxy-2,3-O-isopropylidene-1-O-methyl-β-D-ribo-1,4-furanose-5-ylidene)benzylamine N-oxide 
• 161614-80-8 N-Benzyl-N-[(S)-furan-2-yl-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-methyl]-hydroxylamine 
• 191997-65-6 [(S)-Furan-2-yl-((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-methyl]-carbamic acid benzyl ester 

Relevant academic research and scientific papers

Synthesis of thymine polyoxin c by using l-threonine aldolase-catalyzed aldol reaction

Thymine polyoxin C (2), a common partial structure of polyoxin H (3) and J (4) having anti-fungal activity, was formally synthesized from D-ribose in good overall yield by using L-threonine aldolase-catalyzed reaction as a key step, which affords novel β-hydroxy-α-L-amino acids from glycine and aldehydes in an aqueous medium.

Stereoselective Addition of 2-Furyllithium and 2-Thiazolyllithium to Sugar Nitrones. Synthesis of Carbon-Linked Glycoglycines

A route to epimeric carbon-linked glycoglycines that exploits the stereoselective addition of 2-lithiofuran and 2-lithiothiazole to sugar nitrones has been described. The reaction occurs with opposite diastereofacial selectivity depending on whether the free nitrone or the diethyl aluminum chloride precomplexed derivative is employed. The resulting furyl or thiazolyl hydroxylamines are dehydroxylated to amines by the action of titanium(III) chloride. From these compounds the amino acids are revealed by the oxidative cleavage of the furan ring or by the conversion of the thiazole into the formyl group and oxidation to carboxylic acid. Compounds have been prepared wherein the α-amino acid moiety is installed at C-4 and C-1 of furanoses (ribo, manno, xylo, and lyxo) and at C-5 and C-1 of a pyranose (galacto).

Applications of Sugar Nitrones in Synthesis: The Total Synthesis of (+)-Polyoxin J

A convergent synthesis of the peptidyl nucleoside antibiotic (inhibitor of chitin biosynthesis) polyoxin J (2) by coupling of 5-O-carbamoyl polyoxamic acid (3) and thymine polyoxin C (4) is described. These compounds were prepared by chain elongation and