Validation and Application of an Innovative Protective Group Concept: Enhancing Substrate Reactivity in Glycosylations by Disrupting Intermolecular Interactions

被引：0

作者：

Yano, Kumpei ^{[1
]}

Yoshimoto, Takuya ^{[1
]}

Tsutsui, Masato ^{[1
]}

Manabe, Yoshiyuki ^{[1
,2
]}

Fukase, Koichi ^{[1
,2
,3
,4
]}

机构：

[1] Osaka Univ, Grad Sch Sci, Dept Chem, 1-1 Machikaneyama, Toyonaka, Osaka 5600043, Japan

[2] Osaka Univ, Forefront Res Ctr, 1-1 Machikaneyama, Toyonaka, Osaka 5600043, Japan

[3] Osaka Univ, Ctr Adv Modal, 1-1 Yamadaoka, Osaka, Suita 5650871, Japan

[4] Osaka Univ, DDS, 1-1 Yamadaoka, Suita, Osaka 5650871, Japan

来源：

SYNLETT | 2024年 / 35卷 / 11期

基金：

日本学术振兴会;

关键词：

protecting groups; intermolecular interactions; glycan synthesis; 6-sulfo sialyl Lewis X; sialic acid; SIALYL-LEWIS-X; L-SELECTIN LIGAND; CHEMICAL-SYNTHESIS; CHEMOENZYMATIC SYNTHESIS; CARBOHYDRATE-CHEMISTRY; GLYCANS; ACID; TETRASACCHARIDE; BINDING; OLIGOSACCHARIDES;

D O I：

10.1055/a-2269-7680

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have established an innovative protective approach that disrupts intermolecular interactions to enhance substrate reactivity. Specifically, diacetylimide protection of acetamide prevents the formation of hydrogen bonds, while the incorporation of tert-butyl groups on the aromatic protecting group disrupts pi-stacking interactions, both of which culminate in heightened reactivity in glycosylations. We explored the synergistic implementation of these protective measures and applied them to the synthesis of 6-sulfo sialyl Lewis X.

引用

页码：1253 / 1258

页数：6