α-半乳糖神经酰胺及其C-6修饰类似物的高效合成
Efficient synthesis of α-galactosylceramide and its C-6 modified analogs.
作者信息
Li Huiting, Mao Hongzhao, Chen Chao, Xu Ying, Meng Shuai, Sun Tiantian, Zong Chengli
机构信息
Key Laboratory of Tropical Biological Resources of Ministry of Education, School of Pharmaceutical Sciences, College of Marine Science, Hainan University, Haikou, China.
Anyikang Co., LTD., Shanghai, China.
出版信息
Front Chem. 2022 Nov 25;10:1039731. doi: 10.3389/fchem.2022.1039731. eCollection 2022.
The synthesis of α-galactosylceramide (KRN7000) and its C-6 modified analogs remains a challenge due to the difficult α-1,2--glycosidic bond. A non-participating benzyl (Bn) protecting group has been commonly used to favor the α-glycosylation product. Here, we report the α-selective glycosylation by using a bulky 4,6-O-di--butylsilylene (DTBS) galactosyl donor, regardless of the 2-benzoyl (Bz) participating group. Compared with Bn, Bz groups can be selectively removed in basic conditions without impacting the C-6 azide modification. The azide has the potential for clicking with alkyne or being easily transformed to other functional groups.
由于α-1,2-糖苷键合成困难，α-半乳糖神经酰胺（KRN7000）及其C-6修饰类似物的合成仍然是一个挑战。一种非参与性苄基（Bn）保护基团通常被用于促进α-糖基化产物的生成。在此，我们报道了使用一种庞大的4,6-O-二叔丁基硅亚烷基（DTBS）半乳糖基供体进行α-选择性糖基化反应，而无需考虑2-苯甲酰基（Bz）参与基团。与Bn相比，Bz基团可以在碱性条件下被选择性去除，而不会影响C-6叠氮化物修饰。叠氮化物具有与炔烃发生点击反应的潜力，或者可以很容易地转化为其他官能团。
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