- A two-step preparation of a new C4 chiral building block derivative of D-erythronic acid
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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.
- De Souza,Da Silva,Ferreira
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- Highly Stereoselective Synthesis of β-Glycosides of 3-Deoxy-2-Hexulosonates
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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
- Vlahov, Ioncho R.,Vlahova, Petinka I.,Schmidt, Richard R.
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- A concise synthesis of (+)-botryolide-E and its C-7 epimer
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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.
- Liu, Xiaojing,Chen, Ruijiao,Duan, Feixia,Jia, Junhao,Zhou, Yuqin,Chen, Xiaochuan
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- A new method for the synthesis of 2,3-Aziridino-2,3-Didoxyhexonamides and their conversion into 3-Amino-2,3-Dideoxyhexonic acids
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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
- J?rgensen, Christel,Pedersen, Christian,S?tofte, Inger
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- Total Synthesis of Anti-Influenza Agents Zanamivir and Zanaphosphor via Asymmetric Aza-Henry Reaction
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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.
- Lin, Long-Zhi,Fang, Jim-Min
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- Anticancer and antileishmanial in vitro activity of gold(I) complexes with 1,3,4-oxadiazole-2(3H)-thione ligands derived from δ-D-gluconolactone
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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
- 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
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- Stereoselective Synthesis of the C1-C9 and C11-C25 Fragments of Amphidinolides C, C2, C3, and F
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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.
- Akwaboah, Daniel C.,Wu, Dimao,Forsyth, Craig J.
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supporting information
p. 1180 - 1183
(2017/03/14)
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- A chiron approach to the total synthesis of (-)-juglomycin A, (+)-kalafungin, (+)-frenolicin B, and (+)-deoxyfrenolicin
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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.
- Fernandes, Rodney A.,Chavan, Vijay P.,Mulay, Sandip V.,Manchoju, Amarender
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p. 10455 - 10460
(2013/01/15)
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- A convenient synthesis of hexulosonic acids by IBX mediated oxidation of D-glucono-1,5-lactone derivatives
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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.
- Kolender, Adriana A.,Puenzo, Sol C. Parajon,Varela, Oscar
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scheme or table
p. 237 - 244
(2011/06/10)
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- Total synthesis of (-)-codonopsinol and (+)-2-epi codonopsinol via acid catalyzed amido cyclisation
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A short and stereoselective synthesis of (-)-codonopsinol 5 and its C-2 epimer 6 were accomplished from commercially available starting material d-1,5-gluconolactone, using acid mediated amido cyclisation as the key step. The inhibitory activitiy of these
- Jagadeesh,Reddy, J. Santhosh,Venkateswara Rao,Swarnalatha, J. Lakshmi
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experimental part
p. 1202 - 1207
(2010/03/30)
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- Carbohydrate-based synthetic approach to control toxicity profiles of folate-drug conjugates
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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.
- 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.
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supporting information; experimental part
p. 3685 - 3691
(2010/08/22)
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- Total synthesis of 8-methoxygoniodiol related compounds via chiron approach
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The stereoselective synthesis of 8-methoxygoniodiol related compounds was accomplished by using readily available δ-gluconolactone as a chiral source. The stereoselective addition of an aryl Grignard reagent on an aldehyde, stereoselective reduction of a keto group and regioselective opening of a chiral epoxide by ethyl propiolate are the key steps involved in this synthesis.
- Yadav, Jhillu Singh,Madhava Rao, Batta,Sanjeeva Rao, Kodepelly
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experimental part
p. 1725 - 1730
(2009/12/24)
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- Total synthesis of 8-methoxygoniodiol via chiron approach
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A stereoselective synthesis of 8-methoxygoniodiol is accomplished using readily available δ-gluconolactone as a chiral source. The stereoselective addition of aryl Grignard reagent on aldehyde and regioselective opening of chiral epoxide by ethyl propiola
- Yadav,Madhava Rao,Sanjeevarao,Subba Reddy
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scheme or table
p. 1039 - 1041
(2009/04/06)
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- Isolation synthesis and glycosidase inhibition profile of 3-epi-casuarine
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3-epi-Casuarine, the first naturally occurring stereoisomer of casuarine, was isolated from Myrtus communis L. The glycosidase inhibition profile and NMR spectra of 3-epi-casuarine are compared with those of casuarine; the change in configuration at one of the six stereogenic centres causes a dramatic change in the conformation of the bicyclic system. The key step in the 6% overall yield synthesis of 3-epi-casuarine from d-gluconolactone is the efficient cyclization of a completely unprotected pentahydroxyaminomesylate to the pyrrolizidine nucleus. A low yield synthesis of casuarine is also reported.
- Ameijde, Jeroen Van,Horne, Graeme,Wormald, Mark R.,Dwek, Raymond A.,Nash, Robert J.,Jones, Paul Wyn,Evinson, Emma L.,Fleet, George W.J.
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p. 2702 - 2712
(2007/10/03)
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- SYNTHESIS OF POLYHYDROXYLATED ALKALOIDS
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A process for the production of a polyhydroxylated bicyclic (e.g. pyrrolizidine such as casuarine (10), indolizidine or quinolizidine) alkaloid comprises the cyclisation of a pyrrolidine or piperidine intermediate having three or more free hydroxyl groups
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Page/Page column 27-28; 34-35
(2010/02/15)
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- Convenient enantiopure synthesis of (2S,3R)-2-O-benzyl-3,4-O- isopropylidene-D-erythritol from D-(+)-glucono-δ-lactone: A potential C4 chiral building block
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A new convenient synthesis of (2S,3R)-2-O-benzyl-3,4-O-isopropylidene-D- erythritol has been achieved starting from extremely cheap and commercially available D-(+)-glucono-δ-lactone. It involves two carbon excisions using ozonolysis. The inbuilt stereoch
- Vijayasaradhi, Sivalenka,Beedimane, Manjunath Narayana,Aidhen, Indrapal Singh
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p. 2267 - 2269
(2007/10/03)
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- Synthesis of a New Stable Conformationally Constrained 2,7-Anhydrosialic Acid Derivative
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A stereoseletive synthesis of 2,7-anhydrosialic acid derivative 18 was achieved from D-glucono-δ-lactone. A highly syn-selective addition of Grignard reagent to the N-benzylimine 8 served as a key step.
- Liu, Ke-Gang,Zhou, Hai-Bin,Wu, Yu-Lin,Yao, Zhu-Jun
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p. 9528 - 9531
(2007/10/03)
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- Complex tetrahydrofurans from carbohydrate lactones: THF amino acids as building blocks for unnatural biopolymers
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The multi-gram syntheses of two epimeric six-carbon tetrahydrofurancarboxylates based upon a D-arabinofuranose template are described. An approach to 3-O-benzyl protected derivatives is also detailed. Introduction of nitrogen at C-6 of these scaffolds leads to the generation of building blocks suitable for the generation of oligomers which possess well defined secondary structures. Radical bromination facilitates introduction of nitrogen at C-2, to afford anomeric α-amino acid derivatives which are elaborated to two unnatural diastereomers of the potent herbicidal natural product hydantocidin. X-Ray crystal structures of N-methyl-2-azido-2-deoxy-α-D-arabino-hex-2-ulofuranosonamide and N-dodecyl-2-azido-2-deoxy-β-D-arabino-hex-2-ulofuranosonamide are also disclosed.
- Long, Daniel D.,Smith, Martin D.,Martin, Angeles,Wheatley, Joseph R.,Watkin, David G.,Mueller, Mattaius,Fleet, George W. J.
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p. 1982 - 1998
(2007/10/03)
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- Radical homologation of D-gluconic acid: Highly diastereoselective synthesis of D-gluco-KDO derivatives
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D-glucono 1,5-lactone was converted to O-protected D-gluconic acids. The latter were transformed to gluco-KDO derivatives using Barton ester-based radical chemistry with high diastereoselectivity.
- Barton, Derek H.R,De Almeida, Mauro V,Liu, Wansheng,Shinada, Tetsuro,Jaszberenyi, Joseph Cs,Dos Santos, Hélio F,Le Hyaric, Mireille
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p. 8767 - 8771
(2007/10/03)
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- Reactivity and crystal structure of 1,2:3,4:5,6-Tri-O-isopropylidene-D-gluconolactone
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1,2:3,4,5,6-Tri-O-isopropylidene-D-gluconate (1) undergoes the β-elimination reaction in the presence of LDA to afford 3-deoxy-1,2:5,6-di-O-isopropylidene-D-erythro-hex-3-enolactone (6). Attempts to prepare the phosphonate 4 by reaction of 1 with dimethyl
- Jarosz,Ciunik
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p. 1182 - 1190
(2007/10/03)
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- Highly stereoselective synthesis of α-glycosides of neuraminic acid analogues
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ε-Hydroxy enol ether 6 was readily prepared from D-gluconolactone via ester formation and selective di-O-isopropylidenation, 2-O-alkylation with triflate 1, selective 5,6-de-O-isopropylidenation and 6-O-silylation, azide introduction, and subsequent E-spe
- Vlahov,Vlahova,Schmidt
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p. 7503 - 7506
(2007/10/02)
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- The chemistry of D-gluconic acid derivatives. Part 1. Synthesis of 3,4;5,6-di-O-isopropylidene-D-glucitol and 2,3;4,5-di-O-isopropylidene-aldehydo-D-arabinose from D-glucono-1,5-lactone
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Acid-catalysed isopropylidenation of D-glucono-1,5-lactone with 2,2-dimethoxypropane yields methyl 3,4;5,6-di-O-isopropylidene-D-gluconate.Convenient syntheses of the title compounds from this ester by reduction and oxidation sequences, together with the
- Regeling, Henk,Rouville, Egbert de,Chittenden, Gordon J. F.
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p. 461 - 464
(2007/10/02)
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