Short and Convergent Synthesis of (1→3)-C-Linked Imino Disaccharides (Aza-C-disaccharides)

Zhu, Yugen; Vogel, Pierre

doi:10.1021/jo981781d

Cited by 26 publications

(7 citation statements)

References 23 publications

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“…[5][6][7] Recently we disclosed an efficient and versatile approach to the syntheses of (1?3)-C-disaccharides and (1?3)-C-linked imino disaccharides 5 based on the cross-aldolisation of the aldehydes 3 with the nucleophile 1,4-adducts 2 of isolevoglucosenone 1 (Scheme 1). 8,9 We report here that (1?4)-and (1?2)-Cdisaccharides can be prepared starting from 1 and levoglucosenone 17 with 3, respectively.Adduct 6 of benzyl alcohol with isolevoglucosenone was enolized, without elimination of benzylate anion, on treatment with LiHMDS in 95+5 THF-HMPA at 278 °C (Scheme 2). 9 Quenching of the corresponding lithium enolate with 2-[bis(trifluoromethylsulfonyl)amino]-5-chloropyridine provided the enol triflate 7 in 87% yield.…”

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confidence: 86%

Convergent synthesis of (1→2)- and (1→4)-C-linked imino disaccharides†

Zhu¹,

Vogel²

1999

Chem. Commun.

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A convergent synthesis of (1?2)-and (1?4)-C-linked imino disaccharides was achieved by applying Nozaki-Kishi coupling of a hydroxyproline-derived carbaldehyde with isolevoglucosenone or levoglucosenone derived enol triflates.Carbohydrate mimetics are potentially useful tools to study cellular interactions, 1 the biosynthesis of glycoproteins, the metabolism of glycoconjugates, 2 and the mechanisms of digestion. 3 Inhibitors of the enzymes involved in these processes such as the glycosidases and the glycosyltransferases are potential anti-cancer, antiviral, and antidiabetic agents, as well as insect antifeedant agents. 4 Disaccharide mimetics such as Cdisaccharides and dideoxyiminoalditol C-linked to monosaccharides have emerged as a new class of specific glycosidase inhibitors and may represent non-hydrolyzable epitopes. [5][6][7] Recently we disclosed an efficient and versatile approach to the syntheses of (1?3)-C-disaccharides and (1?3)-C-linked imino disaccharides 5 based on the cross-aldolisation of the aldehydes 3 with the nucleophile 1,4-adducts 2 of isolevoglucosenone 1 (Scheme 1). 8,9 We report here that (1?4)-and (1?2)-Cdisaccharides can be prepared starting from 1 and levoglucosenone 17 with 3, respectively.Adduct 6 of benzyl alcohol with isolevoglucosenone was enolized, without elimination of benzylate anion, on treatment with LiHMDS in 95+5 THF-HMPA at 278 °C (Scheme 2). 9 Quenching of the corresponding lithium enolate with 2-[bis(trifluoromethylsulfonyl)amino]-5-chloropyridine provided the enol triflate 7 in 87% yield. 10 Nozaki-Kishi coupling of 7 and aldehyde 8 led to allylic alcohols 9 and 10 isolated in 62 and 17% yield, respectively. 11,12 ‡ Interestingly, the reaction was accelerated by ultrasound and O 2 . Under N 2 atmosphere, ultrasound shortened the reaction time from 30 to 2 h. While in the presence of a catalytic amount of O 2 (5 mol% with respect to CrCl 2 , concentration of O 2 lower than 10%), the reaction time was reduced further to less than 1 h. Moreover, O 2 suppressed the formation of 11, resulting from H 2 O quenching of the alkenylchromium species, from 36 to less than 10%.

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confidence: 86%

Convergent synthesis of (1→2)- and (1→4)-C-linked imino disaccharides†

Zhu¹,

Vogel²

1999

Chem. Commun.

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“…100 Isolevoglucosenone (187) adds benzyl alcohol to give 190 101. The enolates of ketone 190 do not induce b-elimination at low temperature.…”

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Synthesis of Aza-C-disaccharides (Dideoxyimino-alditols C-Linked to Monosaccharides) and Analogues

Robina¹,

Vogel²

2005

Synthesis

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The first aza-C-disaccharide (D-azaMan-b-CH 2 -(1→6)-D-Man-a-OMe) that mimicks a-D-Manp-(1→6)-a-D-ManOMe was made in 1994 by Johnson and coworkers. Several synthetic approaches to these disaccharide mimetics have been proposed. These are reviewed and compared. Several strategies rely on C-C bond forming reactions such as the Miyaura-Suzuki cross-coupling, the SmI 2 Barbier reaction, the addition of acetylides to aldonolactones, the cross-aldol reaction or the Michael addition of 7-oxabicyclo[2.2.1]heptanone derivatives ('naked sugars'), with subsequent formation of the iminoalditol moieties. Other approaches use nitrogen-containing systems such as sugar-derived nitrones or iminoaldoses that are coupled by either Wittig olefinations, cross-aldol reactions or Takai-Oshima-Nozaki-Kishi reactions. When available, the conformational analysis of the aza-C-disaccharides, as well as their inhibitory activities toward glycosidases, will be summarized.

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“…Conjugated addition of PhSH to 17 (Et 3 N as catalyst) afforded (À)-18 quantitatively. The high exo stereoselectivity of this addition was expected for both kinetic and thermodynamic reasons (steric factor) [17]. The 2-(phenylthio) substituent was introduced to insure stereoselective b-C-glycosidation (see below).…”

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New Nonhydrolyzable Mimetics of Sialyl Lewis X and Their Binding Affinity to P‐Selectin

Carrel

Giraud

Spertini

et al. 2004

Helvetica Chimica Acta

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Wittig olefination of (2S,3R,5S,6R)‐5‐(acetyloxy)‐tetrahydro‐6‐[(methoxymethoxy)methyl]‐3‐(phenylthio)‐ 2H‐pyran‐2‐acetaldehyde ((+)‐10) with {2‐[(2S,3R,4R,5R,6S)‐tetrahydro‐3,4,5‐tris(methoxymethoxy)‐6‐methyl‐ 2H‐pyran‐2‐yl]ethyl}triphenylphosphonium iodide ((−)‐11) gave a (Z)‐alkene derivative (+)‐12 that was converted into (αR,2R,3S,4R,5R,6S)‐tetrahydro‐α,3‐dihydroxy‐2‐(hydroxymethyl)‐5‐(phenylthio)‐6‐{(2Z)‐4‐[(2S,3S,4R,5S,6S)‐tetrahydro‐3,4,5‐trihydroxy‐6‐methyl‐2H‐pyran‐2‐yl]but‐2‐enyl}2H‐pyran‐4‐acetic acid (8), (αR,2R,3S,4R,6S)‐tetrahydro‐α,3‐dihydroxy‐2‐(hydroxymethyl)‐6‐{4‐[(2S,3S,4R,5S,6S)‐tetrahydro‐3,4,5‐trihydroxy‐6‐methyl‐2H‐pyran‐2‐yl]butyl}‐2H‐pyran‐4‐acetic acid (9), and simpler analogues without the hydroxyacetic side chain such as (2S,3S,4R,5S,6S)‐tetrahydro‐6‐methyl‐2‐{(2Z)‐4‐[(2S,3R,5S,6R)‐tetrahydro‐5‐hydroxy‐6‐(hydroxymethyl)‐3‐(phenylthio)‐2H‐pyran‐2‐yl]but‐2‐enyl}‐2H‐pyran‐3,4,5‐triol (30), (2S,3S,4R,5S,6S)‐tetrahydro‐6‐methyl‐2‐{[(2S,5S,6R)‐tetrahydro‐5‐hydroxy‐6‐(hydroxymethyl)‐2H‐pyran‐2‐yl]butyl}‐2H‐pyran‐3,4,5‐ triol ((−)‐41) and (2S,3S,4R,5S,6S)‐tetrahydro‐6‐methyl‐2‐{(2Z/E))‐4‐[(2R,5S,6R)‐tetrahydro‐5‐hydroxy‐6‐(hydroxymethyl)‐2H‐pyran‐2‐yl]but‐2‐enyl}‐2H‐pyran‐3,4,5‐triol (43). The key intermediates (+)‐10 and (−)‐11 were derived from isolevoglucosenone and from L‐fucose, respectively. The following IC50 values were measured in a ELISA test for the affinities of sialyl Lewis x tetrasaccharide, 8, 9, 30, (−)‐41, and 43 toward P‐selectin: 0.7, 2.5–2.8, 7.3–8.0, 5.3–5.9, 5.0–5.2, and 3.4–4.1 mM, respectively.

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Short and Convergent Synthesis of (1→3)-C-Linked Imino Disaccharides (Aza-C-disaccharides)

Cited by 26 publications

References 23 publications

Convergent synthesis of (1→2)- and (1→4)-C-linked imino disaccharides†

Convergent synthesis of (1→2)- and (1→4)-C-linked imino disaccharides†

Synthesis of Aza-C-disaccharides (Dideoxyimino-alditols C-Linked to Monosaccharides) and Analogues

New Nonhydrolyzable Mimetics of Sialyl Lewis X and Their Binding Affinity to P‐Selectin

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