445469-16-9

Basic information

• Product Name: (1'S,2'R,5R)-1-benzyl-5-[1-(tert-butyldimethylsilanyloxy)-2,3-dihydroxypropyl]pyrrolidin-2-one
• Synonyms: (1'S,2'R,5R)-1-benzyl-5-[1-(tert-butyldimethylsilanyloxy)-2,3-dihydroxypropyl]pyrrolidin-2-one
• CAS NO: 445469-16-9
• Molecular Weight: 379.572
• Mol File: 445469-16-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1'S,2'R,5R)-1-benzyl-5-[1-(tert-butyldimethylsilanyloxy)-2,3-dihydroxypropyl]pyrrolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (1'S,2'R,5R)-1-benzyl-5-[1-(tert-butyldimethylsilanyloxy)-2,3-dihydroxypropyl]pyrrolidin-2-one(445469-16-9)
• EPA Substance Registry System: (1'S,2'R,5R)-1-benzyl-5-[1-(tert-butyldimethylsilanyloxy)-2,3-dihydroxypropyl]pyrrolidin-2-one(445469-16-9)

Safety Data

• Hazardous Substances Data: 445469-16-9(Hazardous Substances Data)

Upstream product

• 872174-12-4 (1'S,4''R,5R)-5-[(tert-butyldimethylsilanyloxy)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methyl]pyrrolidin-2-one 
• 190430-55-8 (1'S,2R,4R)-2-[(tert-butyldimethylsilanyloxy)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methyl]-5-oxopyrrolidine-1-carboxylic acid tert-butyl ester 
• 141293-21-2 (1'S,4''R,5R)-1-(tert-butoxycarbonyl)-5-[(2,2-dimethyl-1,3-dioxolan-4-yl)hydroxymethyl]pyrrolidin-2-one 
• 141293-15-4 (1'S,2R,4''R)-2-[(2,2-dimethyl-[1,3]dioxolan-4-yl)hydroxymethyl]-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylic acid tert-butyl ester 
• 445469-15-8 (1'S,4R,5R)-1-benzyl-5-[(tert-butyldimethylsilanyloxy)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methyl]pyrrolidin-2-one 

Downstream Products

• 445469-26-1 (1'S,2'R,5R)-1-benzyl-5-[1-(tert-butyldimethylsilanyloxy)-2,3-bis-(triethylsilanyloxy)propyl]pyrrolidin-2-one 
• 445469-27-2 (2S,2'R,3S)-3-(1-benzyl-5-oxopyrrolidin-2-yl)-3-(tert-butyldimethylsilanyloxy)-2-(triethylsilanyloxy)propionaldehyde 
• 445469-18-1 (1R,4S,5S,6S)-2-benzyl-5,6-bis-(tert-butyldimethylsilanyloxy)-2-azabicyclo[2.2.1]-heptan-3-one 
• 872174-13-5 (1R,4S,5R,6S)-2-benzyl-5,6-bis-(tert-butyldimethylsilanyloxy)-2-azabicyclo[2.2.1]-heptan-3-one 
• 305384-32-1 (1S,2S,3R,5R)-3-amino-5-(hydroxymethyl)cyclopentane-1,2-diol 
• 85026-59-1 (-)-(1R,2R,3S,4R)-4-amino-2,3-dihydroxy-1-(hydroxymethyl)cyclopentane 
• 445469-17-0 (2S,2'R)-(1-benzyl-5-oxopyrrolidin-2-yl)-(tert-butyldimethylsilanyloxy)acetaldehyde 

Relevant articles and documents

Variable strategy toward carbasugars and relatives. 4. Viable access to (4a-carbapentofuranosyl)amines, (5a-carbahexopyranosyl)amines, and amino acids thereof

A chiral, divergent synthesis of two carbafuranosylamines, 1 and 2, two carbapyranosylamines, 3 and 4, two carbafuranosylamino acids, 5 and 6, and two carbapyranosylamino acids, 7 and 8, has been achieved. Highlights of the procedure include the following: a diastereoselective crossed vinylogous Mukaiyama aldol coupling between N-(tert-butoxycarbonyl)-2-[(tert-butyldimethylsilyl)-oxy]pyrrole (TBSOP, 9) and 2,3-O-isopropylidene-D-glyceraldehyde (10) for the assembly of the target compound carbon backbone; a high-yielding silylative cycloaldolization that gives the cyclopentanoid and cyclohexanoid motifs; and a reductive or hydrolytic breakage of the lactam C(O)-N link to liberate the carbasugar and install the desired pseudo-anomeric amine and the hydroxymethyl or carboxyl functionalities. The sequences leading to trans-configured carbafuranosyl compounds 1 and 5 and carbapyranosyl compounds 3 and 7 were 12- and 13-step processes, with overall yields of 34%, 35%, 17%, and 16%. Cis-configured isomers 2, 4, 6, and 8 were obtained only in minor yields.