Unusual ring contraction by substitution of 4-O-activated-pentono-1,5-lactams with cyanide. Stereospecific synthesis of 6-amino-1,4,5,6-tetradeoxy-1,4-imino-hexitols

Godskesen, Michael Anders; Lundt, Inge; Søtofte, Inger

doi:10.1016/s0957-4166(99)00536-4

Cited by 10 publications

(2 citation statements)

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“…The alkene 13 a ent - 10 was prepared using a route that was analogous to an established 18 synthesis of 10 ( Scheme 4 ). Thus, treatment of the lactone 5 (derived from lyxose 19 ) with concentrated hydrochloric acid in acetone gave the corresponding acetonide 20 6 . Treatment of 6 with iodine and triphenylphosphine gave the corresponding iodolactone 7 , which was followed by reductive ring-opening to give the carboxylic acid ent - 8 (whose enantiomer had been used to prepare 18 10 ).…”

Section: Resultsmentioning

confidence: 99%

Evaluation of fluoropyruvate as nucleophile in reactions catalysed by N-acetyl neuraminic acid lyase variants: scope, limitations and stereoselectivity

et al. 2016

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Section: Resultsmentioning

confidence: 99%

Evaluation of fluoropyruvate as nucleophile in reactions catalysed by N-acetyl neuraminic acid lyase variants: scope, limitations and stereoselectivity

et al. 2016

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“…For the diacetonide 8b, it was found that acetic acid/H 2 O (9 : 1) could selectively deprotect the hydroxyl groups in C4 and C5. 20 Hence, 2,3-O-isopropylidene D-lyxonolactone 9 was formed with 70% yield with this strategy.…”

Section: Synthesis Of L-ribose From D-lyxosementioning

confidence: 93%

A heterogeneous Pd–Bi/C catalyst in the synthesis of l-lyxose and l-ribose from naturally occurring d-sugars

2011

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A critical step in the synthesis of the rare sugars, L-lyxose and L-ribose, from the corresponding D-sugars is the oxidation to the lactone. Instead of conventional oxidizing agents like bromine or pyridinium dichromate, it was found that a heterogeneous catalyst, Pd-Bi/C, could be used for the direct oxidation with molecular oxygen. The composition of the catalyst was optimized and the best results were obtained with 5 : 1 atomic ratio of Pd : Bi. The overall yields of the five-step procedure to L-ribose and L-lyxose were 47% and 50%, respectively. The synthetic procedure is advantageous from the viewpoint of overall yield, reduced number of steps, and mild reaction conditions. Furthermore, the heterogeneous oxidation catalyst can be easily separated from the reaction mixture and reused with no loss of activity.

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Nojirimycin

2005

Synthesis of Naturally Occurring Nitrogen Heterocycles From Carbohydrates

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Unusual ring contraction by substitution of 4-O-activated-pentono-1,5-lactams with cyanide. Stereospecific synthesis of 6-amino-1,4,5,6-tetradeoxy-1,4-imino-hexitols

Cited by 10 publications

References 10 publications

Evaluation of fluoropyruvate as nucleophile in reactions catalysed by N-acetyl neuraminic acid lyase variants: scope, limitations and stereoselectivity

Evaluation of fluoropyruvate as nucleophile in reactions catalysed by N-acetyl neuraminic acid lyase variants: scope, limitations and stereoselectivity

A heterogeneous Pd–Bi/C catalyst in the synthesis of l-lyxose and l-ribose from naturally occurring d-sugars

Nojirimycin

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