The particular sensitivity of silyl ethers of D-glucal toward two Vilsmeier-Haack reagents POCl3.DMF and (CF3SO2)2O.DMF. Their unique and selective conversion to the corresponding C(6)-O-formates.
The two electrophilic Vilsmeier-Haack reagents POCl3.DMF 2 or (CF3SO2)2O.DMF 3 mediate the one-step and selective conversion of O-triethylsilyl (O-TES), O-tert-butyldimethylsilyl (O-TBDMS), O-tert-butyldiphenylsilyl (O-TBDPS), and O-triisopropylsilyl (O-TIPS) ethers of D-glucal to the corresponding C(6)-O-formates.
Lellouche
J P
JP
Department of Chemistry, Bar-Ilan University, Ramat-Gan 52900, Israel. lellouj@mail.biu.ac.il
Koeller
S
S