Aminocyclitols. II. Synthesis of thioanalogues of 2,5-dideoxystreptamine
- 1 November 1978
- journal article
- research article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 56 (21) , 2743-2749
- https://doi.org/10.1139/v78-452
Abstract
N,N′-Dibenzoyl-2,5-dideoxystreptamine (8b) reacted with thionyl chloride to form the bisoxazoline 9 and the latter compound was treated with thiobenzoic acid to produce the dithiobenzoate 10a. Removal of the protective groups in 10a afforded (l,3/4,6)-4,6-diamino-1,3-cyclohexanedithiol (1) dihydrochloride. Reaction of 8b with triethyl orthoacetate in the presence of boron trifluoride yielded the monooxazoline 12 which, on reaction with thiobenzoic acid followed by deprotection of the resulting 13a, afforded (d,l)-(13/4,6)-4,6-diamino-3-hydroxycyclohexanethiol (2) dihydrochloride. Similarly, 3-N-benzoyl-1-N-ethoxycarbonyl-2,5-dideoxystreptamine (15) and l-N-benzoyl-3-N-ethoxycarbonyl-2,5-dideoxystreptamine (20) were converted via their respective oxazolines 17a and 22a, to the enantiomeric aminothiols 3 and 4. Protected derivatives of 1–4 are also described.This publication has 0 references indexed in Scilit: