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1-Adamantanol was used in the preparation of 1,3-adamantanediol. It is used in the manufacture of synthetic adamantane derivatives and adapalene.
Koichi Mitsukura; Hiromu Sakamoto; Haruka Kubo; Toyokazu Yoshida; Toru Nagasawa. Bioconversion of 1-adamantanol to 1,3-adamantanediol usingStreptomycessp. SA8 oxidation system. Journal of Bioscience and Bioengineering. 2010, 109 (6), 550-553.
Motowo Yamaguchi; Hiroyuki Kousaka; Shinichi Izawa; Yoshiki Ichii; Takashi Kumano; Dai Masui; Takamichi Yamagishi. Syntheses, characterization, and catalytic ability in alkane oxygenation of chloro(dimethyl sulfoxide)ruthenium(II) complexes with tris(2-pyridylmethyl)amine and its derivatives. Inorganic Chemistry. 2006, 45 (20), 8342-8354.
Carboxyl groups of amino acids have been protected as 1-adamantyl esters via the amino acid tosylate and dimethyl sulfite. The group is readily cleaved with TFA under mild conditions: Synthesis, 1355 (1996). Has also been applied in blocking the ß-carboxyl group of aspartic acid in peptide synthesis; the 1-adamantyl ester is prepared using DCC-DMAP: J. Chem. Soc., Perkin 1, 2129 (1988). See also Appendix 6.
Thiol groups may also be protected by formation of the thioether in TFA. Cleavage is by means of Hg(II) salts: Chem. Pharm. Bull., 26, 1576 (1978).
Reaction with Hydrogen fluoride pyridine complex, L17117, gives 1-fluoroadamantane, a general method for conversion of sec- and tert-alcohols to fluoroalkanes: Org. Synth. Coll., 6, 628 (1988).