(±)-1,2:4,5-Di-O-isopropylidene-myo-inositol

ChemInform Abstract: The “Other” Inositols and Their Phosphates: Synthesis, Biology, and Medicine (with Recent Advances in myo‐Inositol Chemistry)

“…One procedure [19] was used in an earlier study,w here all the compounds in the crude mixture were isolated and used. [26] These compounds include three main benzoylated isopropylidene and di-O-isopropylidene-protected compounds that were used to provide an inexpensive route to racemic conduritol B, C, and Fd erivatives,t hus making it ag ood method to synthesize all the nonchiral inositols.T he benzoyl groups were changed to benzyl groups because of the formation of insoluble benzoylated intermediates.F rom an economic standpoint, the synthesis made use of the organicsolvent-soluble benzoylated derivatives,which usually go into the waste solvent. Theh ighly insoluble 3,6-di-O-benzoyl-1,2:4,5-di-O-isopropylidene-myo-inositol derivative was ap recursor to conduritol C. cis-Inositol cannot be obtained from conduritol derivatives and needed as eparate starting material for its synthesis.T his is an economical method to synthesize some of the meso-inositols from the benzoylated isopropylidene intermediates once the derivatives are isolated from the crude mixture.…”

Synthetic studies on pterin glycosides: the first synthesis of 2′-O-(α-d-glucopyranosyl)biopterin

“…L-Rhamnose, which served as the starting material to obtain the key intermediate 5-deoxy-3-O-PMB-L-arabinose (19), was subjected to glycosidation with allyl alcohol in the presence of hydrochloric acid, followed by acetalization with 2,2-dimethoxypropane, providing allyl 2,3-O-isopropylidene-α-L-rhamnopyranoside (13) 19 (80%) along with the corresponding β-anomer (8%) (Scheme 3). Treatment of 13 with p-methoxybenzyl chloride and sodium hydride in DMF gave the 4-O-PMB derivative 14, which was then converted into the 1-propenyl glycoside 15 with potassium tert-butoxide in DMSO.…”

“…Namely, treatment of 16 with ethanethiol in the presence of p-toluenesulfonic acid in acetic acid gave the dithioacetal 17, which was then oxidized with m-chloroperbenzoic acid (mCPBA) to the corresponding sulfone 18. Degradation of 18 with dilute aqueous ammonia afforded 5-deoxy-3-O-PMB-L-arbinofuranose (19). The selective oxidation for 2-hydroxy group of 19 with cupric acetate 22 provided the L-erythro-pentos-3-ulose derivative 20.…”

Synthesis of a P-1-tethered photoaffinity label for inositol hexakisphosphate binding proteins

“…The starting material, D,L-l,2:4,5-bis-Oisopropylidene-3-(4-methoxybenzyl)-~y~inositol 1, was obtained by a known procedure (20,21). Hydrolysis of the acetone ketal protecting groups (p-TsOH, acetone-water), gave the 3-PMB protected inositol 2 (equivalent to the 1-PMB in racemic form) in 90% yield.…”