140186-66-9

Upstream product

• 4099-85-8 ((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 16205-59-7 2,3,5-tri-O-benzoyl-1-bromo-α-D-erythro-pentofuranose 
• 676618-04-5 2-(β-D-ribofuranosylmercapto)pyridine 
• 96689-78-0 2-pyridyl 2,3,5-tri-O-benzyl-1-thio-β-D-ribofuranoside 
• 140186-54-5 C₃₁H₂₅NO₇S 

Relevant academic research and scientific papers

α-selective ribofuranosylation of alcohols with ribofuranosyl iodides and triphenylphosphine oxide

Ribofuranosylation of a variety of alcohols with ribofuranosyl iodides in the presence of a base and triphenylphosphine oxide afforded the corresponding α-ribofuranosides with diastereoselectivities ≥ 99:1. This reaction can be carried out under mildly basic conditions and is thus compatible with acid-sensitive functional groups.

Stereoselective synthesis of α-linked 2-deoxysaccharides and furanosaccharides by the use of 2-deoxy 2-pyridyl-1-thio pyrano- and furanosides as donors and methyl iodide as an activator

A practical and highly stereoselective glycosidation methodology is described, where anomeric mixture of 2-deoxy 2-pyridyl-1-thiopyranoside donors (1-3,27) have been coupled with several sugar alcohols (4-8,29,31) on activation by methyl iodide to obtain axially linked 2-deoxysaccharides (9-17,30,32,33). Application of this method for the synthesis of disaccharide fragment 28 of avermectin is also described. Utility of this method is also shown by use of 2-pyridyl-1-thiofuranosides (34-36) as donors to prepare α-linked furanosides (42-51).