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.

Short Gram-Scale Synthesis of Sulfavant A / Ziaco, Marcello; Fioretto, Laura; Nuzzo, Genoveffa; Fontana, Angelo; Manzo, Emiliano. - In: ORGANIC PROCESS RESEARCH & DEVELOPMENT. - ISSN 1083-6160. - 24:11(2020), pp. 2728-2733. [10.1021/acs.oprd.0c00393]

Short Gram-Scale Synthesis of Sulfavant A

Marcello Ziaco;Laura Fioretto;Angelo Fontana
;
Emiliano Manzo
2020

Abstract

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.
2020
Short Gram-Scale Synthesis of Sulfavant A / Ziaco, Marcello; Fioretto, Laura; Nuzzo, Genoveffa; Fontana, Angelo; Manzo, Emiliano. - In: ORGANIC PROCESS RESEARCH & DEVELOPMENT. - ISSN 1083-6160. - 24:11(2020), pp. 2728-2733. [10.1021/acs.oprd.0c00393]
File in questo prodotto:
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11588/902328
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 8
  • ???jsp.display-item.citation.isi??? 7
social impact