A concise and practical stereoselective synthesis of ipragliflozin L-proline

• Shuai Ma,
• Zhenren Liu,
• Jing Pan,
• Shunli Zhang and
• Weicheng Zhou

Beilstein J. Org. Chem. 2017, 13, 1064–1070, doi:10.3762/bjoc.13.105

• yield was 52% in three steps and the product purity was excellent. Two key diastereomers were prepared with efficient and direct access to the α-C-arylglucoside. Keywords: arylzinc derivative; β-C-arylglucoside; diastereomer impurity; ipragliflozin L-proline; stereoselective synthesis; Introduction

• , raising the reaction temperature up to −20 °C [11]. However, the yield was not obviously improved. SGLT-2 inhibitors have the common pharmacophore of β-C-arylglucoside, and the synthesis of β-C-arylglucoside including the usage of arylzinc [12], arylalane [13], and anomeric stannane [14] were applied to

• was developed. The route initiated from compound 4a and pivaloyl-protected glycosyl bromide 2b, the β-C-arylglucoside 5 was obtained with high stereoselectivity in one step after a halogen–lithium exchange/transmetalation/coupling sequence. Cryogenic temperatures and catalysts were not required. The