Glucopyranosyl isothiocyanate

T Kinoshita, Y Kasahara, N Nimura. Reversed-phase high-performance liquid chromatographic resolution of non-esterified enantiomeric amino acids by derivatization with 2,3,4,6-tetra-O-acetyl-P-D-glucopyranosyl isothiocyanate and 2,3,4 tri-O-acetyl-a-D-arabinopyranosyl isothiocyanate. J Chromatog 210, 77, 1981. 

Shulman, M.L., Lakhtina, O.E. and Khorlin, A.Y., Specific irreversible inhibition of human and boar 7/-acetyl-/ -D-hexosaminidase by 2-acetamido-2-deoxy-/3-D-glucopyranosyl isothiocyanate. Biochem. Biophys. Res. Commun., 1977, 74, 455. 

Direct and indirect chromatographic methods were developed and compared in systematic examinations for the enantioseparation of P-amino acids direct separation of underivatized analytes involved the use of commercially available Crownpak CR(-I-), teicoplanin, and ristocetin A CSPs [148], while indirect separation was based on precolumn derivatization with 2,3,4,6-tetra-G-acetyl-f)-D-glucopyranosyl isothiocyanate (GITC) or A - a-(2,4-dinitro-5-fluorophenyl)-L-alaninamide (EDAA, Marfey s reagent), with subsequent separation on a nonenantioselective column. 

M. L. Shulman, S. D. Shiyan, and A. Y. Khorlin, Specific irreversible inhibition of sweet-almond p-glucosidase by some p-glycopyranosylepoxyalkanes and p-D-glucopyranosyl isothiocyanate, Biochim. Biophys. Acta, 445 (1976) 169—181. 

To evaluate the enantiomeric purity of (S,S)/(R,R)-statine, racemic mixtures and en-antiomerically enriched samples are analyzed by HPLC after derivatization with 2,3,4,6-tetra-0-acetyl- 3-D-glucopyranosyl isothiocyanate (GITC, 51 Scheme 21 and Table 7).[49 The GITC method also allows the determination of the enantiomeric composition of ethyl esters of statine analogues.[44 491 Another assay to determine the optical purity of statine has been developed, and uses l-G1u-NCA to produce dipeptides with different retention times in HPLC.[18]... 

Isomerization of organic thiocyanates to isothiocyanates is also discussed in other articles.25 29 The first sugar isothiocyanate reported, namely, 2,3,4,6-tetra-O-acetyl-/3- D-glucopyranosyl isothiocyanate (2) was synthesized by Emil Fischer7 in 1914 by treatment of 2,3,4,6-tetra-O-acetyl-a-D-glucopyranosyl bromide (1) with silver thiocyanate in anhydrous xylene. It was also prepared by Muller and Wilhelms8 by thermal isomerization of the corresponding thiocyanate 3, obtained by treatment of 1 with potassium... 

Interestingly, l,3,4,6-tetra-0-acetyl-2-amino-2-deoxy-a-D-glucopyranose hydrobromide (4) reacts with silver thiocyanate31 to give 2-acetamido-3,4,6-tri-0-acetyl-2-deoxy-/3-D-glucopyranosyl isothiocyanate (5), in a reaction which must involve an 0- N acetyl migration. 

D-Glucopyranosyl isothiocyanate 2-acetamido-3,4,6-tri-0-acetyl-2-deoxy- 161 +9.5 CHC13 29... 

Some new 5-(benzylamino)thiatriazoles have been prepared by standard methods.12 5-(Tetra-0-acetyl-/T-D-glucopyranosylamino)-thia-triazole was prepared by the action of HN02 on 4-(tetra-0-acetyl-/3-D-glucopyranosyl)thiosemicarbazide as well as from hydrogen azide and tetra-0-acetyl-/J-D glucopyranosyl isothiocyanate.62 Substituted 5-aminothiatriazoles may be obtained from C-sulfonylthioformamides on reaction with azide ion.63... 

S-1-(1-Napthyl)ethyl isothiocyanate 2,3,4,6-Tetra-0-acetyl-/3-D-glucopyranosyl isothiocyanate 209... 

Toward a complete synthesis of trehazolin (2), 2,3,4,6-tetra-O-benzyl-1 -deoxy-z-D-glucopyranosyl isothiocyanate (7)52 was brought into reaction with the amines 5 and 374 in the presence of triethylamine to afford the x-D-glucopyranosyl thiourea derivatives 375 or 376, respectively (Scheme 46).38 Subsequent treatment with 2-chloro-3-ethylbenzoxazolium tetrafluoroborate and triethylamine afforded the corresponding amino oxazoline derivatives 377 and 378. Finally, hydrogenation over Pd(OH)2 on carbon afforded trehazolin (2). 

The 6 -deoxy-6 -fluoro trehazolin 460 has been synthesized (Scheme 68).120 2,3,4-Tri-0-benzyl-6-deoxy-6-fluoro-a-D-glucopyranosyl isothiocyanate (457) was... 

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