3006-56-2Relevant academic research and scientific papers
Synthesis of several optically active O-methyl-inosamines and -inosadiamines from L-quebrachitol
Ogawa, Seiichiro,Isaka, Akihiro
, p. 105 - 123 (2007/10/02)
A series of p-toluenesulfonic and methanesulfonic esters of L-quebrachitol have been prepared starting from the di-O-isopropylidene derivative of the cyclitol.Nucleophilic displacement of these sulfonates with azide ion in 2-methoxyethanol produced the az
Cyclitol Reactions, V. - Synthesis of Enantiomerically Pure Valienamine from Quebrachitol
Paulsen, Hans,Heiker, Fred R.
, p. 2180 - 2203 (2007/10/02)
An enantioselective synthesis of Valienamine (86) from quebrachitol (L-2O-methyl-chiro-inositol) (1) is described.Valienamine (86) is an unsaturated branched-chain aminocyclitol found in the central structural unit of the antidiabetic drug acarbose.Techniques for the introduction of side chains, azido groups, and double bonds into inositol systems are investigated.The methods developed in this connection are applied in the synthesis of valienamine.
Cyclitol Reactions, IV. Synthesis of Enantiomeric Conduritols and Amino-Conduritols
Paulsen, Hans,Roeben, Wolfgang,Heiker, Fred R.
, p. 3242 - 3252 (2007/10/02)
The key-intermediate for all syntheses described in this paper is the 1-O-tosylate 7 of quebrachitol (1).This leads, via 8, to the 1L-conduritol B (5) and, via 13, to the 1L-conduritol F (17).Selective displacement of the equatorial tosyloxy group in comp
