140193-76-6

Basic information

• Product Name: 5-(N-benzylamino)-6,7-O-isopropylidene-2,3,5-trideoxy-D-ribo-hept-2-enonic acid 1,4-lactone
• Synonyms: 5-(N-benzylamino)-6,7-O-isopropylidene-2,3,5-trideoxy-D-ribo-hept-2-enonic acid 1,4-lactone
• CAS NO: 140193-76-6
• Molecular Weight: 303.358
• Mol File: 140193-76-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 5-(N-benzylamino)-6,7-O-isopropylidene-2,3,5-trideoxy-D-ribo-hept-2-enonic acid 1,4-lactone(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(N-benzylamino)-6,7-O-isopropylidene-2,3,5-trideoxy-D-ribo-hept-2-enonic acid 1,4-lactone(140193-76-6)
• EPA Substance Registry System: 5-(N-benzylamino)-6,7-O-isopropylidene-2,3,5-trideoxy-D-ribo-hept-2-enonic acid 1,4-lactone(140193-76-6)

Safety Data

• Hazardous Substances Data: 140193-76-6(Hazardous Substances Data)

Upstream product

• 100777-91-1 (2S)-2,3-O-isopropylideneglyceraldehyde N-benzylimine 
• 121896-38-6 2-tert-butyldimethylsilyloxyfuran 
• 100-46-9 benzylamine 
• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 61550-02-5 (furan-2-yloxy)-trimethylsilane 
• 131319-74-9 (R)-2,3-di-O-isoproylideneglyceraldehyde N-benzylimine 

Downstream Products

• 227095-33-2 (3R,5S,6S)-3-benzyl-5-<(tert-butyldimethylsilyl)oxy>-6-formylpiperidin-2-one 
• 227095-32-1 (3R,5S,6S,4'S)-3-benzyl-5-<(tert-butyldimethylsilyl)oxy>-6-(2,2-dimethyldioxolan-4-yl)piperidin-2-one 
• 140193-70-0 1-O-trimethylsilyl-5-(N-benzyl-N-benzoxycarbonylamino)-2,3;6,7-di-O-isopropylidene-D-glycero-D-allo-heptofuranose 
• 140193-69-7 5-(N-benzyl-N-benzoxycarbonylamino)-2,3;5,6-di-O-isopropylidene-5-deoxy-D-glycero-D-allo-heptono-1,4-lactone 
• 208649-02-9 (2S,3S)-3-hydroxypipecolic acid 
• 676144-83-5 (1R,2S,3S,4S,5S)-4-tert-butoxycarbonylamino-2,5-bis(tert-butyldimethylsilanyloxy)-3-triethylsilanyloxycyclohexanecarboxylic acid 
• 676144-84-6 (1S,2S,3S,4S,5S)-[3,6-bis(tert-butyldimethylsilanyloxy)-4-hydroxymethyl-2-triethylsilanyloxycyclohexyl]carbamic acid tert-butyl ester 
• 676144-78-8 (1'S,5S,6S)-1-benzyl-6-(1,2-bis(triethylsilanyloxy)ethyl)-5-(tert-butyldimethylsilanyloxy)piperidin-2-one 
• 676144-80-2 (1S,4R,5S,6S,7S)-2-benzyl-5,7-bis(tert-butyldimethylsilanyloxy)-6-triethylsilanyloxy-2-azabicyclo[2.2.2]octan-3-one 
• 676144-79-9 (2S,2'S,3'S)-[1-benzyl-3-(tert-butyldimethylsilanyloxy)-6-oxopiperidin-2-yl]triethylsilanyloxyacetaldehyde 
• 676144-76-6 (4'S,5S,6S)-1-benzyl-5-(tert-butyldimethylsilanyloxy)-6-(2,2-dimethyl-[1,3]dioxolan-4-yl)piperidin-2-one 
• 676144-77-7 (1'S,5S,6S)-1-benzyl-5-(tert-butyldimethylsilanyloxy)-6-(1,2-dihydroxyethyl)piperidin-2-one 
• 676144-75-5 (4'S,5S,6S)-1-benzyl-6-(2,2-dimethyl-[1,3]dioxolan-4-yl)-5-hydroxypiperidin-2-one 

Relevant articles and documents

A formal synthesis of thymine polyoxin C

A convergent stereoselective synthesis of thymine polyoxin C 1 has been conducted utilizing the benzylimine of D-glyceraldehyde acetonide 7 as a chiral controller and 2-trimethylsilyloxy furan 8 as a four-carbon synthon. In the presence of catalytic BF3·OEt2, 8 has been found to add to 7 with a moderately high level of stereoselectivity. Intermediate 4-(aminoalkyl)-2-butenolide 6 proved to be an ideal candidate for elaboration to 3.

Diastereoselective synthesis of a novel lactam peptidomimetic exploiting vinylogous Mannich addition of 2-silyloxyfuran reagents

The total synthesis of a potential inhibitor of HIV-protease-the chiral nonracemic six-membered hydroxy lactam 6-has been accomplished, that involves, as key reaction, the highly diastereoselective vinylogous Mannich addition of furan-based silyloxy diene 7 to glyceraldeyde imine 8.

Total synthesis of 1,5-dideoxy-1,5-iminoalditols

Enantiomerically pure 1,5-dideoxy-1,5-imino-D-glycero-D-allo-heptitol (10) has been synthesized in ca. 9% overall yield by utilizing 2,3-O-isopropylidene-D-glyceraldehyde-N-benzylimine (1) as a chiral source and 2-(trimethylsiloxy)furan (2) as a homologative reactant. The opening move was the preparation of properly protected seven-carbon butenolide 4, followed by diastereoselective anti, cis-dihydroxylation of the lactone double bond and furanose-to-azapyranose ring expansion. This generated a piperidine intermediate 7, the stereochemistry of which was secured by a single crystal X-ray analysis of its diacetate 9.