Adamantoyl chloride

The adamantoate ester is formed selectively from a primary hydroxyl group (e.g., from the 5 -OH in a ribonucleoside) by reaction with adamantoyl chloride, Pyr (20°, 16 h). It is cleaved by alkaline hydrolysis (0.25 N NaOH, 20 min), but is stable to milder alkaline hydrolysis (e.g., NH3, MeOH), conditions that cleave an acetate ester. ... 

C11H19O2 828-51-3) see Betamethasone adamantoate 1-adamantoyl chloride (C,H,5C10 2094-72-6) see Rimantadine adenosine cyclic 3, S -(hydrogen phosphate)... 

Both 1-adamantyl chloroformate 209) (114) and 1-adamantoyl chloride 347) (115) have been found to be useful blocking agents in biochemical syntheses. 

Adamantoyl chloride (115) serves as a protecting group for the 5 position of deoxynucleosides (Eq. (83)) 347)- The adamantoyl group may be readily removed by mild base. 

Starting materials for the corresponding adamant-1-yl derivative are lithium bis(trimethylsilyl)-phosphide-2tetrahydrofuran and adamantoyl chloride. ... 

This hindered acid chloride has been suggested also for use in nucleoside synthesis for the protection of the 5 -primary hydroxyl group.5 1-Adamantoyl chloride reacts in benzene-pyridine solution with 2 -desoxy-5-fluorouridine (3) to give a crystalline... 

R = Ac) was converted into (52 R = H) in good yield [52]. The pivaloyl protecting group may be removed by alkaline hydrolysis [52, 109] or with MeNH2 in aqueous or aqueous alcoholic solution [52]. 1-Adamantoyl chloride (53) shows similar selectivity in its reactions with deoxyribonucleosides, and the esters obtained are again comparatively resistant to alkaline hydrolysis [110]. 

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