The chemistry of L-ascorbic and D-isoascorbic acids. 1. The preparation of chiral butanetriols and -tetrols

Abushanab, Elie; Vemishetti, Purushotham; Leiby, Robert W.; Singh, Harpreet; Mikkilineni, Amarendra B.; Wu, David C. J.; Racha, Saibaba; Panzica, Raymond P.

doi:10.1021/jo00246a037

Cited by 166 publications

(71 citation statements)

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“…Oxidative cleavage of the ene-diol double bond of this starting material, followed by esterification of the ensuing carboxylate to the corresponding ethyl -erythronate 7, had already been described by Abushanab and co-workers, [12] and Demuynck and coworkers. [13] O-Benzylation of 7 (BnBr/Ag 2 O/KI/4Å MS/ toluene) gave 8 (83%), which was quantitatively reduced (DIBAH/toluene at Ϫ78°C) to aldehyde 9, a compound that readily condenses with water to afford the hydrated form of the aldehyde.…”

Section: Arabinose Series 3 and Ribose Seriesmentioning

confidence: 65%

Synthesis of Imidazolo-Piperidinopentoses as Nagstatine Analogues

et al. 2001

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The syntheses of the four imidazolo-piperidino-pentoses 3−6, which belong to the D-series, and of their L-enantiomers, ent-3 to ent-6, are reported. Ascorbic acid and isoascorbic acid were converted over several steps into the L-threo/ L-erythro-and the D-erythro/D-threo-configured aldotetroses, respectively, which are the key building blocks for the eight target imidazolo-pentoses cited above. Nucleophilic addition of a metallated imidazole to any one of these four aldotetroses gave the corresponding two diastereomeric adducts, intramolecular cyclisation of which provided the expected bicyclic target molecules, with some protection and deprotection steps being unavoidable prerequisites. The structures and configurations of all eight piperidinoses in Scheme 1 were determined unambiguously, by a combination of 1 H/ 13 C NMR spectroscopy, circular dichroism (CD)

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Section: Arabinose Series 3 and Ribose Seriesmentioning

confidence: 65%

Synthesis of Imidazolo-Piperidinopentoses as Nagstatine Analogues

et al. 2001

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“…The protected (2S,3S)-1-deoxy-1-iodobutanethreitol (19) was obtained from (S)-2-(benzyloxy)-2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethanol (17) according to the procedure of Abushanab and coworkers. [12] Compound 17, was in itself derived from -ascorbic acid (16).…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Glycosidase Inhibitory Activities of Pyrrolidines and Piperidines with N‐(Polyhydroxyalkyl) Side Chains

et al. 2007

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Amidification of L‐proline (3) with (+)‐(R,R)‐6 and (–)‐(S,S)‐tartaric anhydride diacetate (7) gave N‐substituted L‐proline derivatives 8a,b, respectively. Acids 8a,b were transformed into diesters 9a,b with MeOH/HCl. Similar reactions with methyl (2S,4R)‐4 and (2R,4S)‐4‐acetoxypipecolate (5) led to bicyclic lactams 14a,b and 15a. Compounds 8a,b were converted into N‐(trihydroxybutyl)pyrrolidine derivatives 8c,d, 10a,b and 11a,b. Methyl (2S,4R)‐20a and (2R,4S)‐4‐acetoxy‐N‐[(2S,3S)‐1,2,3‐trihydroxybutyl]pipecolate (20b) were obtained by displacement of (–)‐(2S,2S)‐2‐O‐benzyl‐3,4‐O‐isopropylidene‐1‐deoxy‐1‐iodothreitol (19) by 4 and 5. Compounds 20a,b were converted into (2S,4R,2′S,2′S)‐21a and(2R,4S,2′S,3′S)‐4‐hydroxy‐2‐hydromethyl‐N‐(2‐benzyloxy‐3,4‐isopropylidenedioxy)piperidine (21b) and finally into unprotected pentols 22a,b. Nonprotected (2S,2′S,3′S)‐11a and (2S,2′R,3′R)‐N‐(1,2,3‐trihydroxybutyl)prolinol (11b), as well as 22a,b, did not inhibit any of the 13 glycosidases assayed. However, a triacetoxy derivative, (2S,3S)‐2,3‐diacetoxy‐4‐[(2R,4S)‐4‐acetoxy‐2‐(methoxycarbonyl)piperidin‐1‐yl]‐4‐oxobutanoic acid (13b) is an inhibitor (IC50 = 157 μM) of α‐L‐fucosidase from bovine kidney.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

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“…5 Mesylation and subsequent reduction with NaBH 4 converted acetonide 2 to a selectively mesylated diol. Sequential treatment of NaH with the mesylate and addition of PhMgBr to the resulting oxirane in the presence of CuI produced the known alcohol 3 in 80% overall yield.…”

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confidence: 99%