3716-14-1

Upstream product

• 1871-57-4 2-chloromethyl-3-chloroprop-1-ene 
• 108-95-2 phenol 
• 548482-49-1 5-methylene-1,3,2-dioxathiane 2-oxide 

Downstream Products

• 16440-42-9 α,α'-Bis--isobuten 
• 90860-09-6 2,2-di(phenoxymethyl)oxirane 

Relevant academic research and scientific papers

Easy access to derivatives of 2-(hydroxymethyl)propane-1,2,3-triol (isoerythritol) with up to four separately addressable functionalities

5-Methylene-2-oxo[1,3,2]dioxathiane (2) was obtained in 91% yield from 2-methylenepropane-1,3-diol (1) and thionyl chloride. The cyclic sulfite 2 reacts with a variety of nucleophiles to give formally monosubstituted products 3 of the diol 1 in 62-77% yield. Oxidation of 2 with RuCl3/NaIO4 yields the diprotected tetraol 5-(hydroxymethyl)-2,2-dioxo[1,3,2]-dioxathian-5-ol (7) in 86% yield, which can be used to easily access tetrafunctional derivatives of 2-(hydroxymethyl)propane-1,2,3-triol (isoerythritol); for example, acetylation with acetic anhydride furnishes in 96% yield the primary acetate 11, which reacts with potassium cyanide and sodium azide to give the 2-cyano- and 2-(azidomethyl)propane-1,2,3-triol monoacetates 12a,b (78 and 82% yield, respectively). Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.