Improved synthesis of dicyclohexylidene protected quebrachitol and its use in the synthesis of l-chiro-inositol derivatives

Orthogonally Protected Cyclohexanehexols by a “One Reaction – One Product” Approach: Efficient Access to Cyclitols and Their Analogs

“…Alkylation of one of the hydroxy groups in 30 with (4‐chloro)benzyl bromide, followed by inversion of the second hydroxy group via its triflate, gave the chiro ‐inositol derivative 32 (Scheme ). A perusal of the earlier reports reveals that much time and effort has been invested in attempts to prepare protected chiro ‐inositol derivatives such as 33 (starting from chiro ‐inositol), with little success 7c,7e…”

2H1C Mimicry: Bioinspired Iron and Zinc Complexes Supported by N,N,O Phenolate Ligands

“…The degradation of the ligand in this manner is somewhat unexpected given the poor leaving group ability generally associated to methyl groups. However, demethylation of protected hydroxyl groups through CÀ Ο bond cleavage has been reported in the presence of strong Lewis acids such as BBr 3 , [43,44] AlCl 3 , [45] and FeCl 3 . [46,47] We hypothesise that reaction of K-Im Ph2 NNO with FeCl 3 initially produces a blue-coloured intermediate diiron(III) complex, [Fe 2 (Im Ph2 NNO) 2 (Cl) 4 ] (A), which contains two ferric ions within the dinuclear, cyclic complex architecture associated to the ligand's μ 2 -coordination mode (Scheme 7).…”

Quebrachitol: Global Status and Basic Research

“…Apart from these, Almeida et al have studied a simple route to synthesize some azido and amino inositol derivatives, starting from QCT [ 58 ]. In order to optimize the procedure and improve the yield, a modified synthesis of 1 l -1,2:3,4-di- O -cyclohexylidene-5- O -methyl-chiro-inositol, which QCT was used as the original material, has been accomplished by Barrs et al [ 59 ].…”