158227-67-9

Upstream product

• 58479-61-1 tert-butylchlorodiphenylsilane 
• 130222-84-3 5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone 
• 174590-91-1 8-O-(tert-butyldiphenylsilyl)-1,2,3-trideoxy-5,6-O-isopropylidene-α,β-D-ribo-oct-1-en-4-ulofuranose 

Relevant academic research and scientific papers

Highly regio- and diastereoselective, acidic clay supported intramolecular nitrile oxide-alkene cycloaddition on d-ribose derived nitriles: An efficient synthetic route to isoxazoline fused five and six membered carbocycles

An efficient synthetic route to isoxazoline fused carbocycles from carbohydrate scaffolds that comprise of free hydroxyl group(s) is described with high regio- and stereoselectivity. Montmorillonite K-10/chloramine T oxidation and in situ intramolecular nitrile oxide-alkene cycloaddition (INOC) of d-ribose derived oximes have been developed for the diversity oriented synthesis of isoxazoline fused five and six membered carbocycles.

Enantiospecific synthesis of (-)-5-epi-shikimic acid and (-)-shikimic acid

Diastereoselective reaction of 2,3-O-isopropylidene-D-ribose with allylmagnesium chloride gave a 5 : 1 mixture of triols 4 and 5, which were then converted to nitrones 8 and 9. Intramolecular nitrone cycloaddition gave the isoxazolidines 10 and 11, which on acetylation gave the corresponding acetates 12 and 13 which were separated by repeated crystallisation. The major adduct 12 was converted to (-)-5-epi-shikimic acid 2. Reaction of the ribonolactone derivative 20 with allylmagnesium chloride gave the hemiacetal 21. Reduction of compound 21 with DIBAL afforded exclusively the diol 22, which was desilylated to give the triol 5. Similar chemistry to that employed for the synthesis of (-)-5-epi-shikimic acid 2 with the diol 5 resulted in the synthesis of (-)-shikimic acid 1.

Diastereoselective reduction of hemiacetals derived from 2,3-o-isopropylidene derivatives of carbohydrate lactones

Reactions of organomagnesium and/or organolithium reagents with 2,3-O-isopropylidene-D-erythronolactone and 5-O-tertbutyldiphenylsilyl-2,3-O-isopropylidene-D-ribonolactone gave good yields of the corresponding hemiacetals which, by choice of hydride reage

Enantiospecific synthesis of (-)-5-epi-shikimic acid and a new route to (-)-shikimic acid

(-)-Shikimic acid (1) and (-)-5-epi-shikimic acid (2) have each been prepared enantiospecifically and with high diastereoselectivity from D-ribose.