434308-98-2

Basic information

• Product Name: (1'S,2'R)-2,6-dimethoxy-4-[2'-dibenzylamino-1'-(tert-butyldimethylsilanyloxy)-4'-hydroxybutyl]pyrimidine
• Synonyms: (1'S,2'R)-2,6-dimethoxy-4-[2'-dibenzylamino-1'-(tert-butyldimethylsilanyloxy)-4'-hydroxybutyl]pyrimidine
• CAS NO: 434308-98-2
• Molecular Weight: 537.775
• Mol File: 434308-98-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (1'S,2'R)-2,6-dimethoxy-4-[2'-dibenzylamino-1'-(tert-butyldimethylsilanyloxy)-4'-hydroxybutyl]pyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: (1'S,2'R)-2,6-dimethoxy-4-[2'-dibenzylamino-1'-(tert-butyldimethylsilanyloxy)-4'-hydroxybutyl]pyrimidine(434308-98-2)
• EPA Substance Registry System: (1'S,2'R)-2,6-dimethoxy-4-[2'-dibenzylamino-1'-(tert-butyldimethylsilanyloxy)-4'-hydroxybutyl]pyrimidine(434308-98-2)

Safety Data

• Hazardous Substances Data: 434308-98-2(Hazardous Substances Data)

Upstream product

• 60186-89-2 4-bromo-2,6-dimethoxy-pyrimidine 
• 100-39-0 benzyl bromide 
• 434308-74-4 (1'S,2'R)-2,6-dimethoxy-4-(2'-dibenzylamino-1'-hydroxy-4'-trityloxybutyl)pyrimidine 
• 434308-72-2 (R)-2,6-dimethoxy-4-(2'-dibenzylamino-4'-trityloxybutanoyl)pyrimidine 
• 434308-70-0 (3R)-3-dibenzylamino-2-hydroxy-2-(2,6-dimethoxypyrimidin-4-yl)tetrahydrofuran 
• 434308-68-6 (R)-2-dibenzylamino-4-hydroxybutyric acid lactone 
• 434308-76-6 (1'S,2'R)-2,6-dimethoxy-4-[2'-dibenzylamino-1'-(tert-butyldimethylsilanyloxy)-4'-trityloxybutyl]pyrimidine 

Downstream Products

• 265652-18-4 cylindrospermopsin 
• 434309-02-1 (3R,4aS,7R,8S)-8-(4-Bromo-benzyloxymethyl)-3-[(S)-(tert-butyl-dimethyl-silanyloxy)-(2,6-dimethoxy-pyrimidin-4-yl)-methyl]-7-methyl-hexahydro-pyrido[1,2-c]pyrimidine-1,6-dione 
• 434309-04-3 (3R,4aS,6S,7R,8S)-8-(4-Bromo-benzyloxymethyl)-3-[(S)-(tert-butyl-dimethyl-silanyloxy)-(2,6-dimethoxy-pyrimidin-4-yl)-methyl]-6-hydroxy-7-methyl-octahydro-pyrido[1,2-c]pyrimidin-1-one 
• 434308-80-2 C₃₄H₅₃BrN₄O₇Si 

Relevant articles and documents

Total synthesis of (-)-7-epicylindrospermopsin, a toxic metabolite of the freshwater cyanobacterium Aphanizomenon ovalisporum, and assignment of its absolute configuration

(Chemical Equation Presented) The Z and E nitrones 38 and 39 from condensation of aldehyde 20 with hydroxylamine 36 underwent intramolecular dipolar cycloaddition to give the substituted 1-aza-7-oxobicyclo[2.2.1] heptanes 40 and 41 in a ratio of 2:1, respectively. Reductive N-O bond cleavage of 40 followed by carbonylation gave cyclic urea 47 in which inversion of the secondary alcohol was effected via an oxidation-reduction sequence. After conversion of the p-bromobenzyl ether 50 to azide 54, activation of the cyclic urea as its O-methylisourea and reduction of the azide led to spontaneous cyclization to afford the tricyclic nucleus 59 of cylindrospermopsin. Global deprotection, including hydrolysis of the 2,4-dimethyoxypyrimidine appendage to a uracil, and then monosulfation of the resultant diol 60 afforded a substance identical with natural (-)-7-epicylindrospermopsin (1). The asymmetric synthesis of (-)-7-epicylindrospermopsin defines its absolute configuration as 7S,8R,10S,12S,13R,14S.