55721-08-9Relevant academic research and scientific papers
Sodium hydride/hexamethylphosphoric triamide: A new and efficient reagent towards the synthesis of protected 1,2- and 5,6-enopyranosides
Khan,Perveen,Ali Shah,Shekhani,Voelter
, p. 896 - 898 (2001)
A new method for the elimination of hydrogen halides and p-toluenesulfonic acid from sugar moieties using sodium hydride (NaH) in hexamethylphosphoric triamide (HMPA) at room temperature is reported. NaH/HMPA has several advantages compared to NaH/DMF: elimination products are produced in high yields even from sterically hindered starting materials, and not only from halides, but also tosylates.
A method for the syntheses of Enopyranosides
Khan, Khalid M.,Perveen, Shahnaz,Al-Qawasmeh, Raed A.S,Shekhani, Mohammed S.,Shah, Syed T. Ali,Voelter, Wolfgang
experimental part, p. 191 - 196 (2010/04/23)
Sodium hydride (NaH) in hexamethylphosphoric triamide (HMPA) has been introduced as an economical and efficient reagent towards the creation of 1, 2- or 5, 6-enopyranosides from the corresponding halogenated or tosylated pyranosides. NaH/HMPA has several advantages compared to NaH/DMF: elimination products are produced in high yields even from sterically-hindered halides as well as tosylates. 2009 Bentham Science Publishers Ltd.
Synthesis and utility of 2-(benzoyloxyimino)-2-deoxy-α-D-lyxo-hexopyranosyl bromide as a novel α-D-talosaminide building block
Kaji, Eisuke,Osa, Yumiko,Takahashi, Keiko,Zen, Shonosuke
, p. 15 - 20 (2007/10/03)
A novel α-D-talosaminyl donor, 2-(benzoyloxyimino)-2-deoxy-α-D-lyxo-hexopyranosyl bromide has been synthesized in a total yield of 32% over 6 steps from D-galactose. The utility of the donor was evaluated for the elaboration of α-D-TalNAc-(1→6)-α-D-Gal, α-D-TalNAc-(1→6)-α-D-Glc, and α-D-TalNAc-(1→3)-L-serine derivatives by a simple 3-step sequence, comprising α-selective glycosylation of appropriately protected acceptors of D-galactose, D-glucose, and L-serine, talo-selective hydroboration of the oxyimino function to an amino group, and N-acetylation.
ALTERNATIVE SYNTHESES AND RELATED N.M.R. STUDIES OF PRECURSORS FOR INTERNAL β-D-GALACTOPYRANOSYL RESIDUES IN OLIGOSACCHARIDES, ALLOWING CHAIN EXTENSION AT O-4
Kovac, Pavol,Taylor, Richard B.
, p. 153 - 174 (2007/10/02)
Crystalline 2,3,6-tri-O-benzoyl-4-O-(bromoacetyl)-α-D-galactopyranosyl chloride (5) was prepared from methyl 2,3,6-tri-O-benzoyl-4-O-(bromoacetyl)-α- or -β-D-galactopyranoside by cleavage with dichloromethyl methyl ether (DCMME) in the presence of zinc ch
