Chiral glycerol ethers synthesis

Scheme 3. Synthesis of chiral glycerol ethers starting from (D)-mannitol (12).

Alkylations of phenols with epichlorohydrin under PTC conditions and microwave irradiation were described twice in 1998. Subsequently, ring-opening reactions of the epoxide group were also performed using microwaves (Eqs. 20 and 21) [31, 32]. In the first catalytic synthesis of chiral glycerol sulfide ethers was described [31] in the second biologically active amino ethers were prepared [32],... 

The synthesis of chiral acyclic nucleosides 276 utilizes the readily available protected acetoxymethyl ether of glycerol 275, which reacted with silylated nucleobases under phase transfer conditions using dibenzo-18-crown-6 to give N-9 purinyl and N-1 pyrimidinyl acyclonucleosides. Removal of the benzoyl groups by methanolic ammonia gave 277 (88JMC144 89TL6165). 

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