114743-85-0Relevant articles and documents
A two-step preparation of a new C4 chiral building block derivative of D-erythronic acid
De Souza,Da Silva,Ferreira
, p. 1339 - 1340 (1998)
1,2;3,4-Di-O-isopropylidene-D-erythronic acid (2,2,2′,2′-Tetramethyl-[R,R-(4,4′-bi-1,3-dioxolan)]-5-one) 4, a new C4 chiral building block derivative of D-erythronic acid was prepared in two steps from D-glucono-δ-lactone.
Highly Stereoselective Synthesis of β-Glycosides of 3-Deoxy-2-Hexulosonates
Vlahov, Ioncho R.,Vlahova, Petinka I.,Schmidt, Richard R.
, p. 293 - 296 (1993)
ε-Hydroxy (Z)-enol ethers 6 and 12 were readily prepared from D-glucono-1,5-lactone by ring openning, 2-O-alkylation with triflate 3, and Z-specific β-elimination.Cyclization of 6 and 12 induced by PhSeBF4 or by PhSeOTf provided exclusivaly β-connected di
A concise synthesis of (+)-botryolide-E and its C-7 epimer
Liu, Xiaojing,Chen, Ruijiao,Duan, Feixia,Jia, Junhao,Zhou, Yuqin,Chen, Xiaochuan
, p. 3947 - 3950 (2017)
The first synthesis of (+)-botryolide-E and its C-7 epimer has been achieved in 8 steps from D-Glucono-δ-lactone, and their antibiotic activities were also investigated preliminarily.
A new method for the synthesis of 2,3-Aziridino-2,3-Didoxyhexonamides and their conversion into 3-Amino-2,3-Dideoxyhexonic acids
J?rgensen, Christel,Pedersen, Christian,S?tofte, Inger
, p. 325 - 328 (1998)
Two new 2,3-aziridino-2,3-dideoxyhexonamides 3 and 11 were prepared by a three-step procedure from commercially available D-glucono-1,5-1actone and D- gulono-1,4-1actone, respectively. The lactones were converted into methyl 3,4:5,6-diO-isopropylidene-2-O
Total Synthesis of Anti-Influenza Agents Zanamivir and Zanaphosphor via Asymmetric Aza-Henry Reaction
Lin, Long-Zhi,Fang, Jim-Min
, p. 4400 - 4403 (2016)
The potent anti-influenza agents, zanamivir and its phosphonate congener, are synthesized by using a nitro group as the latent amino group at C4 for asymmetric aza-Henry reaction with a chiral sulfinylimine, which is derived from inexpensive d-glucono-?-lactone to establish the essential nitrogen-containing substituent at C5. This method provides an efficient way to construct the densely substituted dihydropyran core of zanamivir and zanaphosphor without using the hazardous azide reagent.
Anticancer and antileishmanial in vitro activity of gold(I) complexes with 1,3,4-oxadiazole-2(3H)-thione ligands derived from δ-D-gluconolactone
Espinosa, Andrés Villase?or,Costa, Danilo de Souza,Tunes, Luiza Guimar?es,Monte-Neto, Rubens L. do,Grazul, Richard Michael,de Almeida, Mauro Vieira,Silva, Heveline
, p. 41 - 50 (2021)
Four gold(I) complexes conceived as anticancer agents were synthesized by reacting [Au(PEt3)Cl] and [Au(PPh3)Cl] with ligands derived from δ-d-gluconolactone. The ligands’ structure was designed to combine desired biological properti
Stereoselective Synthesis of the C1-C9 and C11-C25 Fragments of Amphidinolides C, C2, C3, and F
Akwaboah, Daniel C.,Wu, Dimao,Forsyth, Craig J.
supporting information, p. 1180 - 1183 (2017/03/14)
An efficient synthesis of the C1-C9 and the C11-C25 fragments of amphidinolides C, C2, C3, and F from a common intermediate is reported. The construction of the C1-C9 fragment involves an intramolecular hetero-Michael cyclization to form the 3,5-disubstituted trans-tetrahydrofuran moiety. The approach to prepare the C11-C25 fragment utilizes a highly stereoselective aerobic cobalt-catalyzed alkenol cyclization and a chelated Mukaiyama aldol reaction to form the C13-C14 bond and to concomitantly install the C13 hydroxyl group.
A chiron approach to the total synthesis of (-)-juglomycin A, (+)-kalafungin, (+)-frenolicin B, and (+)-deoxyfrenolicin
Fernandes, Rodney A.,Chavan, Vijay P.,Mulay, Sandip V.,Manchoju, Amarender
, p. 10455 - 10460 (2013/01/15)
A general, efficient, and common strategy for the synthesis of (-)-juglomycin A, (+)-kalafungin, (+)-frenolicin B, and (+)-deoxyfrenolicin is reported here. The strategy involves the synthesis of a key building block alkyne from a cheap chiral pool material, d-glucono-δ-lactone, Doetz benzannulation, oxa-Pictet-Spengler reaction, and H2SO 4-mediated epimerization.
A convenient synthesis of hexulosonic acids by IBX mediated oxidation of D-glucono-1,5-lactone derivatives
Kolender, Adriana A.,Puenzo, Sol C. Parajon,Varela, Oscar
scheme or table, p. 237 - 244 (2011/06/10)
The oxidation of the free hydroxyl group of methyl 3,4:5,6-di-O- isopropylidene-D-gluconate 2 or its 2,3:5,6-di-O-isopropylidene analogue 3, the products of acetonation of D-glucono-1,5-lactone 1, has been attempted by alternative procedures. The oxidation of OH-2 in 2, or OH-4 in 3, with o-iodoxybenzoic acid (IBX) took place to afford the respective 2-keto 4 and 4-keto 7 derivatives in almost quantitative yields. In contrast, the oxidations with pyridinium dichromate were unsuccessful, and those using dimethylsulfoxide?acetic anhydride afforded low yields of 4 or 7. Selective removal of the isopropylidene groups in 4 or 7 with 88% aqueous acetic acid afforded, respectively, the methyl esters 5 or 8; whereas treatment with aqueous trifluoroacetic acid led to the free hexulosonic acids 6 or 9. The tautomeric preferences for the oxidation products 4 and 7, and their derivatives, have been established by 13C NMR spectroscopy. ARKAT-USA, Inc.
Carbohydrate-based synthetic approach to control toxicity profiles of folate-drug conjugates
Vlahov, Iontcho R.,Santhapuram, Hari Krishna R.,You, Fei,Wang, Yu,Kleindl, Paul J.,Hahn, Spencer J.,Vaughn, Jeremy F.,Reno, Daniel S.,Leamon, Christopher P.
supporting information; experimental part, p. 3685 - 3691 (2010/08/22)
Figure presented To better regulate the biodistribution of the vinblastine-folate conjugate, EC145, a new folate-spacer that incorporates 1-amino-1-deoxy-d-glucitol-γ-glutamate subunits into a peptidic backbone, was synthesized. Synthesis of Fmoc-3,4;5,6-di-O-isopropylidene-1-amino-1-deoxy- d-glucitol-γ-glutamate 20, suitable for Fmoc-strategy solid-phase peptide synthesis (SPPS), was achieved in four steps from δ-gluconolactone. Addition of alternating glutamic acid and 20 moieties onto a cysteine-loaded resin, followed by the addition of folate, deprotection, and cleavage, resulted in the isolation of the new folate-spacer: Pte-γGlu-(Glu(1-amino-1-deoxy- d-glucitol)-Glu)2-Glu(1-amino-1-deoxy-d-glucitol)-Cys-OH (21). The addition of 21 to an appropriately modified desacetylvinblastine hydrazide (DAVLBH) resulted in a conjugate (25) with an improved therapeutic index. Treatment of 25 with DTT in neutral buffer at room temperature demonstrated that free DAVLBH would be released under the reductive environment of the internalized endosome.
