A More Convenient and General Procedure for O-Monobenzylation of Diols via Stannylenes: A Critical Reevaluation of the Bu2SnO Method
- 29 May 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 68 (13) , 5426-5428
- https://doi.org/10.1021/jo026794c
Abstract
A more consistent, straightforward, and economical protocol for generation of stannylene species and their reaction with BnBr leading to products of O-monobenzylation of diols has been set. It has shown to be specially indicated for substrates bearing vicinal trans 1,2-diol moieties on cyclohexane backbones, which are more resistant to these transformations. Such protocol has been successfully applied to myo-inositol derivatives and acyclic diols.Keywords
This publication has 18 references indexed in Scilit:
- Chemoenzymatic Synthesis of Neoglycopeptides: Application to an α-Gal-Terminated NeoglycopeptideThe Journal of Organic Chemistry, 2001
- Synthesis, Acid−Base Behavior, and Binding Properties of 6-Modified myo-Inositol 1,4,5-Tris(phosphate)sJournal of Medicinal Chemistry, 1999
- Total Synthesis of (−)-Reserpine Using the Chiron ApproachThe Journal of Organic Chemistry, 1997
- Pentagon IP3: Synthesis of a Ring-Contracted Mimic of a Second MessengerJournal of the American Chemical Society, 1995
- The synthesis and resolution of (±)-1,4-diO-benzyl-2,3-O-isopropylidene-myo-inositolCarbohydrate Research, 1994
- Synthesis and tritium radiolabelling of fluorinated analogues of myo-inositolJournal of the Chemical Society, Perkin Transactions 1, 1992
- An Efficient O-Monoalkylation of Dimethyl l-Tartrate via O-Stannylene Acetal with Alkyl Halides in the Presence of Cesium FluorideChemistry Letters, 1987
- A mild procedure for the regiospecific benzylation and allylation of polyhydroxy-compounds via their stannylene derivatives in non-polar solventsJournal of the Chemical Society, Perkin Transactions 1, 1981
- Complete regiospecificity in the benzylation of a cis-diol by the stannylidene procedureJournal of the Chemical Society, Chemical Communications, 1976
- Preparation and Synthetic Utility of Some Organotin Derivatives of nucleosidesThe Journal of Organic Chemistry, 1974