Practical synthesis of latent disarmed S-2-(2-propylthio)benzyl glycosides for interrupted Pummerer reaction mediated glycosylation

Xu, Yang; Zhang, Qian; Xiao, Ying; Wu, Pinru; Chen, Wei; Song, Zejin; Xiao, Xiong; Meng, Lingkui; Zeng, Jing; Wan, Qian

doi:10.1016/j.tetlet.2017.05.014

Cited by 7 publications

(3 citation statements)

References 39 publications

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“…Mp 152-154 °C (Lit. 37 Hz, 1 H, H-1), 6.28 (dd, J 3,4 = 10.3 Hz, J 4,5 = 10.2 Hz, 1 H, H-4), 6.07 (dd, J 2,3 = 3.3 Hz, 1 H, H-3), 5.91 (dd, 1 H, H-2), 4.70 (dd, part A of ABX, J 5,6a = 2.5 Hz, J 6a,6b = 12.4 Hz, 1 H, H-6a), 4.57 (ddd, J 5,6b = 3.8 Hz, 1 H, H-5), 4.50 (dd, part B of ABX, 1 H, H-6b). 13 The 1 H and 13 C NMR spectra were in accordance with the literature.…”

Section: 2346-penta-o-benzoyl--d-mannopyranose (4)mentioning

confidence: 99%

C-5 Epimerisation of d-Mannopyranosyl Fluorides: The Influence of Anomeric Configuration on Radical Reactivity

Ferro,

See,

Pierens

et al. 2023

Synthesis

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The fluorine-directing effect has so far been exploited to provide short and efficient synthetic routes to rare L-ido sugars. However, the importance of anomeric configuration to its success has remained experimentally unverified. We now report on the synthesis of α- and β-configured per-O-benzoylated mannopyranosyl fluorides and initially show that their reactivity towards photo-bromination is strongly dependent on the anomeric configuration. The stereochemical basis of the fluorine-directing effect is then validated by revealing the striking difference in stereoselectivity observed for the free radical reductions of the isolated 5-C-bromo sugars. This work importantly provides a synthetic route to a donor-functionalised derivative of L-gulose and reveals new insights into the behaviour of glycosyl radicals.

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Section: 2346-penta-o-benzoyl--d-mannopyranose (4)mentioning

confidence: 99%

C-5 Epimerisation of d-Mannopyranosyl Fluorides: The Influence of Anomeric Configuration on Radical Reactivity

Ferro,

See,

Pierens

et al. 2023

Synthesis

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“…Consequently, stable 2-(isopropylthio)benzyl chloride (PTB-Cl) was used instead of PTB-I in the coupling reactions without affecting the efficiency, which allowed gram-scale synthesis to be achieved (Scheme 9). 23 Another approach to SPTB glycoside synthesis is via the direct reaction of peracylated glycosides 6B with 2-(isopropylthio)benzyl thiol (PTB-SH) in the presence of BF 3 •Et 2 O (Scheme 10). This protocol also offered various SPTB glycosides in good yields.…”

Section: Account Syn Lettmentioning

confidence: 99%

“…Although α/β-mixtures were obtained in several cases, these mixtures did not affect the subsequent glycosylation reactions. 23…”

Section: Account Syn Lettmentioning

confidence: 99%

Interrupted Pummerer Reaction in Latent/Active Glycosylation

Meng

Zeng

Wan

2017

Synlett

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A latent/active glycosylation strategy is efficient for rapid assembly of oligosaccharides. We recently developed novel OPTB/OPSB and SPTB/SPSB glycosides as two pairs of latent/active glycosyl donors. The active OPSB and SPSB glycosyl donors are efficiently activated by Tf2O via an interrupted Pummerer reaction mechanism. In this account, the design, developments, mechanism studies and applications of these new glycosylation methodologies are described.1 Introduction2 Conceiving Ideas3 Synthesis of OPSB and SPSB Glycosides4 Substrate Scope5 Application in the Synthesis of Natural Products6 Conclusion

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Glycosyl Sulfoxides in Glycosylation Reactions

et al. 2018

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Carbohydrate chemistry has benefited a lot from the intrinsic reactivity of sulfoxide since it was introduced in glycosylation reactions by Kahne in 1989. Since then, extensive studies have been explored by employing sulfoxide as glycosyl donors and activation reagents in construction of glycosidic bonds. As glycosyl donors, the sulfinyl groups could locate either directly or remotely at anomeric position. This chapter focuses on the establishment and development of sulfoxides as glycosyl donors in glycosylation reactions, with an emphasis on their applications and postulated mechanisms.

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Practical synthesis of latent disarmed S-2-(2-propylthio)benzyl glycosides for interrupted Pummerer reaction mediated glycosylation

Cited by 7 publications

References 39 publications

C-5 Epimerisation of d-Mannopyranosyl Fluorides: The Influence of Anomeric Configuration on Radical Reactivity

C-5 Epimerisation of d-Mannopyranosyl Fluorides: The Influence of Anomeric Configuration on Radical Reactivity

Interrupted Pummerer Reaction in Latent/Active Glycosylation

Glycosyl Sulfoxides in Glycosylation Reactions

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