… of secondary hydroxyl groups in the O-alkylation of carbohydrate-related primary-secondaryvic-glycols. Regioselective 2-O-benzylation of 1, 3: 2, 4-di-O-ethylidene-D- …

EA El'perina, MI Struchkova, MI Serkebaev…

Index: El'perina, E. A.; Struchkova, M. I.; Serkebaev, M. I.; Serebryakov, E. P. Russian Chemical Bulletin, 1993 , vol. 42, # 4 p. 744 - 750 Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1993 , # 4 p. 776 - 781

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Abstract

Abstract Partial O-alkylation of 1, 3: 2, 4-di-O-ethylidene-D-glucitol (1a), 1, 2-O- isopropylidene-3-O-methyl-α-D-glucofuranose (1b), and R-(+)-1-O-benzylglycerol (1c) with benzyl chloride in a KOH/DMSO system results in products of monoalkylation at the secondary (4a–c) and at the primary hydroxyl (2a–c) in ratios of over 95∶ 5 (a),∼ 2∶ 1 (b), and∼ 1∶ 1 (c), whereas (±) propane-1, 2-diol (1d) gives only the product of 1-O- ...