92512-33-9Relevant academic research and scientific papers
High-Yielding Diastereoselective syn-Dihydroxylation of Protected HBO: An Access to D-(+)-Ribono-1,4-lactone and 5-O-Protected Analogues
Moreaux, Maxime,Bonneau, Guillaume,Peru, Aurélien,Brunissen, Fanny,Janvier, Marine,Haudrechy, Arnaud,Allais, Florent
supporting information, p. 1600 - 1604 (2019/01/14)
A diastereoselective chemoenzymatic synthetic pathway to D-(+)-ribono-1,4-lactone, a versatile chiral sugar derivative widely used for the synthesis of various natural products, has been designed from cellulose-based levoglucosenone (LGO). This route involves a sustainable Baeyer-Villiger oxidation of LGO to produce enantiopure (S)-γ-hydroxymethyl-α,β-butenolide (HBO) that is further functionalized with various protecting groups to provide 5-O-protected γ-hydroxymethyl-α,β-butenolides. The latter then undergo a diastereoselective and high-yielding syn-dihydroxylation of the α,β-unsaturated lactone moiety followed by a deprotection step to give D-(+)-ribono-1,4-lactone. Through this 4-step synthetic route from LGO, D-(+)-ribono-1,4-lactone is obtained with d.r. varying from 82:18 to 97:3 and in overall yields between 32 and 41 % depending on the protecting group used. Moreover, valuable synthetic intermediates 5-O-tert-butyldimethylsilyl-, 5-O-tert-butyldiphenylsilyl- as well as 5-O-benzyl-ribono-1,4-lactones are obtained in 3 steps from LGO in 58, 61 and 40 %, respectively.
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
Raveendranath,Blazis,Agyei-Aye,Hebbler,Gentile,Hawkins,Johnson,Baker
, p. 207 - 223 (2007/10/02)
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
Chiral Bicycles from Ribonolactone
Mann, John,Thomas, Alison
, p. 737 - 738 (2007/10/02)
The preparation of the chiral butenolide (4b) is described, together with its use in annulation reactions yielding stereochemically defined bicyclo, , and ring systems; the synthetic utility of these species is indicated.
A Convenient Procedure for the Deoxygenation and Homologation of D-Ribose Derivatives
Attwood, Stephen V.,Barrett, Anthony G.M.
, p. 1315 - 1322 (2007/10/02)
5-O-Acetyl- and 5-O-diphenyl-t-butylsilyl-2,3-di-O-acetyl-D-ribonolactones were converted into the corresponding 3-deoxy-2-O-acetyl-D-arabinolactone derivatives (9a) and (9b) by sequential reaction with 1,8-diazabicycloundec-7-ene and hydrogen over
