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. 2019 Sep 10;24(18):3288. doi: 10.3390/molecules24183288

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© 2019 by the authors.

Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).

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Scheme 1 — Preparation of tert-butyl-N-{4,6-bis[(1,7-dicarba-closo-dodecaboran-9-ylmethyl)1,7-dicarba-closo-dodecaboran-9-ylthio]-1,3,5-triazin-2-yl}-N-(1′,2′:3′,4′-di-O-isopropylidene-6′-deoxy-α-d-galacto-pyranos-6′-yl)glycinate (7). a) I₂, AlCl₃, CH₂Cl₂, rt, 2 d, 92% [62,63]; b) paraformaldehyde, n-BuLi, tetrahydrofuran (THF), rt, overnight, 89%; c) Br₂, PPh₃, benzene, reflux, 46 h, 95% [64,65,66]; d) from 3—Mg, THF, reflux, 2 h; e) from 1—11 mol% CuI, 4 mol% [PdCl₂(PPh₃)₂], THF, reflux, 2 d, 30% [61,62,63,64,67,68]; f) S₂Cl₂, AlCl₃, CH₂Cl₂, reflux, 4 h, 67% [69]; g) Zn, HCl_conc., glacial acetic acid (HOAc), ethyl acetate, reflux, 4 h, 81% [69]; h) +8, K₂CO₃, MeCN, reflux, 2 d, 79%.