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Tetrahedron Letters
Volume 27, Issue 2, 1986, Pages 155-158

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doi:10.1016/S0040-4039(00)83965-9

Desulfurization of glycosyl isothiocyanates with tributyltin hybride

Zbigniew J. Witezak

Department of Biochemistry, Purdue University West Lafayette, Indiana 47907 U.S.A.

Received 23 October 1985.

Available online 8 March 2001.

Abstract

Desulfurization of glycosyl isothiocyanates with tributyltin hydride in the presence of AIBM led to the formation of 1,5-anhydro-D,-alditols intermediate isocyanides.

References

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The starting 2,3,4-tri- -acetyl-β-g-xylopyranose isothiocyanate ( ) was prepared according to the recent procedure of M.J. Camarasa, P. Fernandez-Resa, M.T. Garcia-Lopez, F.C. De Las Heras, P.P. Mondez-Castrillon and A. San Felix Synthesis 509 (1984) M.p. 72-73°(ether/hexane); [α]₂₀^D–31.2° (c 1.2 CHC1₃); ¹H-NMR (200 MHz), 1.95, 2.02, 2.06 (S 9H, 3x OAc) 5.9 (t, 1H, J_2,3 = J_3,4 = 4Hz, H–3), 4.8(d 1H, J_1,2 = 9Hz H–1), 4.5–4.2 (m, 3H H–1,2,4) 4.07(q 1H, J_5a,5e = 12 Hz, H–5e), 3.4 (q 1H, H–5a); ¹³C-NMR (50.3 MHz); 91.7 (C-1), 69.4 (C–2), 70.9 (C–3), 68.2 (C–4), 62.6 (C–5) and 141.3 (N---C---S). Anal. Calc. for C₁₂H₁₅NO₇S; C, 45.41 ;H,4.36; N,4.41; Found: C, 45.02; H, 4.6; N, 4.69. .

The starting 2,3,4-tri- -acetyl-β-L-arabinose isothiocyanate ( ) was prepared according to the method of K.K. De, G.T. Shiau and R.E. Harmon J. Carbohydr. Nucleos. Nucleot. 2 (1975), p. 171 [α]₂₀^D - 45.5° (c. 1.0 CHCl₃); ¹H-NMR (200 MHz); 1.87, 1.93, 2.00 (s 9H, 3x CH₃CO–) 4.1 (q 1H, J_5a,5e = 12Hz, H–5e, 3.8 q 1H, H–5e), 4.86 (d 1H, J_1,2 = 9 Hz, H–1), 5.16 (q 1H, J_3,4 10Hz,' J_3,4 3.2 Hz, H–3), 5.4 (q 1H, H–2), ¹³C-NMR (50.3 MHz); 93.8 (C–1), 69.3 (C–2), 69.8 (C–3), 69.8 (C–4), 63.6 (C–5), 141.4 (N= =S). . View Record in Scopus | Cited By in Scopus (1)

¹H-NMR (200 MHz); (CDC1₃), 1,87, 1.93, 1.96, (s 9H 3x 0Ac), 2.01 (s 3H NAc), 4.1 – 3.4 broad m (H–2,3,4,5) 4.29 (d, 2H, H–6,6), 4.67 (d 1H, J_1,2 12 Hz H–1), 6.27d (1H, J = 8Hz NH), ¹³C-HMR (50.3 MHz); 102,3 (C–1), 56.0 (C–2), 74.3 (C–3), 70.6 (C–4), 76.1 (C–5), 61.5 (C–6), 164.1 ( =C:), Anal. Calc. for C₁₄H₂₀N₂O₉; C, 46.66; H, 5.59; N, 7.77; Found: C, 46.18; H, 5.67; N, 7.31.

¹H-NMR (60 MHz); (CDC1₃), 1.97, 2.01, 2.09 (s 9H 3x0Ac), 5.1 (t 1H H-3), 4.86 (d 1H, J_1,2 = 9Hz H–1), 4.6−4.2 (m 3H H–1,2,4, 4.1 (q 1H H–5), 3.4 (q IH - H–5). ¹³C-NMR (50.3 MHz); (CDC1₃) 91.7 (C–1), 69.4 (C–2), 70.9 (C–3), 68.3 (C–4), 62.6 (C–5), 164.3 ( =C:); Anal. Calc. for C₁₂H₁₅NO₇; C, 50.52; H, 5.3; N, 4.91; Found: C, 49.96; H, 5.41; N, 4.58.

¹H-NMR (60 MHz); (CDC1₃,) ; 1.86, 1.91, 2.01 (S, 9H 3xOAc), 4.16 (q H–5), 3.86 (q 1H H–5¹), 4.79 (d 1H J_1,2, = 9 Hz, H–1, 5.0 (q 1H H–3), 5.46 (q 1H H–2). ¹³C-NMR (50.3 MHz); (CDC1₃) 93.7 (C–1),'69.1 (C–2), 69.6 (C–3), 69.6 (C–4) 63.5 (C–5), 164.1 ( =C:). Anal. Calc. for C₁₂H₁₅NO₇; C, 50.52; H, 5.3; S, 4.91; Found: C, 50.02; H, 5.01; N, 4.69.

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Tetrahedron Letters
Volume 27, Issue 2, 1986, Pages 155-158

Result list | previous < 9 of 36 > next

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