Recently, we reported the promising activity of a novel class of sulfoquinovosyl-diacylglycerols named Sulfavants as molecular vaccine adjuvants. Herein, we describe a modified and improved chemical synthesis of the lead product Sulfavant A (1), with the aim to produce from milligrams to 10 g of the pure compound that is necessary for the preclinical development. Starting from the versatile synthesis based on the trichloroacetimidate methodology, up-scaled preparation of Sulfavant A (1) was achieved in 11 steps by elimination and modification of those reactions that negatively affected the overall yield by the previous procedure. The novel strategy gave 17% overall yield of the target compound 1 and also paved the way for the gram-scale preparation of a wide range of other charged and neutral glycoglycerolipids.

中文翻译：

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短克级合成硫磺剂A

最近，我们报道了一种新型新型磺基喹喔基-二酰基甘油，名为分子硫酸盐佐剂，作为分子疫苗佐剂。在本文中，我们描述了一种改良和改进的主产物磺胺类药物A（1）的化学合成方法，旨在产生从毫克到10 g的纯化合物，这对于临床前开发是必需的。从基于三氯乙亚氨酸盐方法学的通用合成开始，通过消除和修饰那些对先前过程不利地影响总收率的反应，可以在11个步骤中大规模制备Sulfavant A（1）。新策略使目标化合物1的总收率达到17％ 并为克级制备多种其他带电和中性的甘油脂铺平了道路。