157831-29-3

Upstream product

• 60933-68-8 3,4,6-tri-O-benzyl-β-D-arabinofuranoside 
• 157831-25-9 (2R,3R,4R,5S)-1,3,4-Tris-benzyloxy-5-(4-methoxy-benzylamino)-hept-6-en-2-ol 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 560130-10-1 (2R,3S,4R)-1,3,4-tribenzyloxy-5-(4-methoxyphenyl)methylamino-6-hepten-2-ol 
• 157831-24-8 ((3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-(4-methoxy-benzyl)-amine 
• 157831-26-0 (3S,4R,5S)-3,4-dibenzyloxy-1-(4-methoxyphenylmethyl)-5-vinylpyrrolidin-2-one 
• 157831-27-1 (3S,4R,5S)-3,4-dibenzyloxy-5-hydroxymethyl-1-(4-methoxyphenyl)methyl-pyrrolidin-2-one 
• 157831-28-2 (3S,4R,5S)-3,4-dibenzyloxy-5-hydroxymethyl-pyrrolidin-2-one 
• 560130-12-3 (3S,4R,5S)-3,4-dibenzyloxy-5-(t-butyldimethylsiloxy)methyl-pyrrolidin-2-one 

Downstream Products

• 560130-14-5 diethyl (3R,4R,5S)-2-[3,4-dibenzyloxy-5-(t-butyldimethylsiloxy)methylpyrrolidin-2-ylidene]malonate 
• 157831-30-6 diethyl (3R,4R,5S)-2-(3,4-dibenzyloxy-5-hydroxymethylpyrrolidin-2-ylidene)malonate 
• 157831-31-7 diethyl (3R,4R,5S)-2-[3,4-dibenzyloxy-5-(methanesulfonyloxy)methylpyrrolidin-2-ylidene]malonate 
• 560130-36-1 (2S,3R,4R)-3,4-Bis-benzyloxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-[5-oxo-2-phenyl-oxazol-(4E)-ylidene]-pyrrolidine-1-carboxylic acid allyl ester 
• 161150-49-8 (3R,4R,5S)-2-[(E)-1-benzoylamino-1-[N-(1-methylethyl)carbamoyl]methylidene]-3,4-dibenzyloxy-1-(2-propenyloxy)carbonyl-5-(t-butyldimethylsiloxy)methylpyrrolidine 
• 161275-47-4 (3R,4R,5S)-2-[(Z)-1-benzoylamino-1-[N-(1-methylethyl)carbamoyl]methylidene]-3,4-dibenzyloxy-1-(2-propenyloxy)carbonyl-5-(t-butyldimethylsiloxy)methylpyrrolidine 
• 161150-51-2 (3R,4R,5S)-2-[(E)-1-benzoylamino-1-[N-(1-methylethyl)carbamoyl]methylidene]-3,4-dibenzyloxy-1-(2-propenyloxy)carbonyl-5-methanesulfonyloxymethylpyrrolidine 
• 560130-29-2 4-[(3R,4R,5S)-3,4-dibenzyloxy-5-(methanesulfonyloxy)methylpyrrolidin-2-ylidene]-2-phenyl-4H-oxazol-5-one 
• 560130-26-9 (3R,4R,5S)-2-[1-benzoylamino-1-[N-(1-methylethyl)carbamoyl]methylidene]-3,4-dibenzyloxy-5-methanesulfonyloxymethylpyrrolidine 

Relevant academic research and scientific papers

Synthetic studies of carzinophilin. Part 2: Synthesis of 3,4-dibenzyloxy-2-methylidene-1-azabicyclo[3.1.0]hexane systems corresponding to the C1-C17 fragment of carzinophilin

A model compound bearing the C1-C17 fragment of carzinophilin was synthesized. The synthesis involved coupling reaction of a cyclic thioimidate with the 4H-oxazol-5-one derivative, ring-opening of the 4H-oxazol-5-one to furnish a dehydropeptide system, elaboration of the C1-C6 enolamide, and construction of the aziridine ring as key steps.

A Stereoselective Synthesis of a Novel Model Compound of Carzinophilin Carrying the C6-C13 Unit with Correct Stereochemistry

The title synthesis was achieved by featuring stereocontrolled elaboration of the functionalized pyrrolidine-2-thione from 2,3,5-tri-O-benzyl-β-D-arabinofuranose and base-induced construction of an aziridine ring from the 5-mesyloxymethylpyrrolidine.