121687-51-2

Upstream product

• 693-03-8 n-butyl magnesium bromide 
• 99315-76-1 (5S)-5-(tert-butyldiphenylsiloxymethyl)-2(5H)-furanone 
• 109-72-8 n-butyllithium 
• 5336-08-3 D-Ribono-1,4-lactone 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 99315-75-0 (-)-5-O-(diphenyl-t-butylsilyl)-2,3-O-(thiocarbonyl)-D-ribono-1,4-lactone 
• 92512-33-9 (3R,4S,5R)-5-((tert-butyldiphenylsilyloxy)methyl)-3,4-dihydroxydihydrofuran-2(3H)-one 
• 130222-84-3 5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone 
• 30725-00-9 2,3-O-isopropylidene-D-ribonic-γ-lactone 

Downstream Products

• 121687-62-5 3-C-butyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-D-erythro-pentofuranose 
• 121687-70-5 1-<3-C-butyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-β-D-erythro-pentofuranosyl>thymine 
• 121709-61-3 1-<3-C-butyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-α-D-erythro-pentofuranosyl>thymine 
• 121687-55-6 1-O-acetyl-3-C-butyl-5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-α,β-D-erythro-pentofuranose 

Relevant academic research and scientific papers

Amino acids, XV: Synthesis of enantiopure DAVA-derivatives (5-amino-4-hydroxypentanoic acids) from (S)-glutamic acid

Starting from (S)-glutamic acid the readily available hydroxymethyl lactone 1 is protected as the TBDPS ether 2. Alkylation of the lithium enolate of 2 provides the lactones 3a,b with high diastereomeric excess. On the other hand 1,4 addition of Gilman cuprates to 10 furnishes the alcohols 12a,b after deprotection. Transformation of 4,12 via the mesylates 5,13 and the azides 6,14 affords the Boc protected amines 7,15 after catalytic hydrogenation in the presence of Boc2O. After treatment of 7,15 with methanolic HCl the rings of the crystalline hydrochlorides 8,16 are opened to the DAVA-derivatives (δ-aminovaleric acid derivatives) 9,17.

A synthetic route to 3-C-alkyl (or 3-C-phenyl-) 2,3-dideoxy-D-erythro- pentono-1,4-lactones: Intermediates in the synthesis of 2(3H)-furanones

A series of 3-C-alkyl- (and 3-C-phenyl-) 2,3-dideoxy-D-erythro-pentono- 1,4-lactones, compounds which are important in the synthesis of modified nucleosides and antibiotic sugars, were synthesized from D-ribonolactone. By a route that proceeded via 5-O-pr

Synthesis and evaluation of a series of 1-(3-alkyl-2,3-dideoxy-alpha,beta-D-erythro-pentofuranosyl)thymines.

A series of 1-(3-alkyl-2,3-dideoxy-alpha,beta-D-erythro-pentofuranosyl)thymines (3'-alkyl-3'-deoxythymidines) has been prepared from 5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-D-glycero-pent-2- enono-1,4-lactone ((S)-5-[(tert-butyldiphenylsilyl)oxymethyl]-2(5H)- furanone) by Michael addition of the appropriate organocopper reagent, followed by reduction of the lactone, acetylation of the resulting hemiacetal, and trimethylsilyl triflate-catalyzed coupling with 2,4-di-O-(trimethylsilyl)thymine. The protected nucleosides were desilylated by using tetrabutylammonium fluoride to give anomeric mixtures of the free nucleosides. The unsubstituted 2',3'-dideoxynucleoside analog was similarly prepared from 5-O-(tert-butyldiphenylsilyl)-2,3-dideoxy-D-glycero-pentono- 1,4-lactone ((S)5-[(tert-butyldiphenylsilyl)-oxymethyl]-dihydro-2(3H)-fu r anone).