K. V. Rao et al. / Carbohydrate Research 345 (2010) 2709–2713
2713
preparation the following article was published: Regioselective Reductive
Ring Opening of Benzylidene Acetals Using Triethylsilane and Iodine,
Panchadhayee, R.; Misra, A. K. Synlett 2010, Advanced online publication:
4.59 (q, J = 11.9 Hz, 2H, ArCH2), 4.38 (d, 1H, J = 9.6 Hz, H-1), 3.85–
3.72 (m, 3H, H-5, H-6a,b), 3.59 (m, 1H, H-4), 2.15 (s, 3H, SCH3),
2.09, 2.06 (2s, 6H, 2 ꢂ COCH3). Anal. Calcd for C18H24O7S
(384.12): C, 56.24; H, 6.29. Found: C, 56.26; H, 6.30.
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1.8. Methyl 2,3,6-tri-O-benzyl-1-thio–D
-glucopyranoside (25)27
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dH (300 MHz, CDCl3): 7.39–7.25 (m, 15H, Ar-H), 4.94 (d, 1H,
J = 11.4 Hz, ArCH2), 4.89 (d, 1H, J = 10.2 Hz, ArCH2), 4.81 (d, 1H,
J = 11.7 Hz, ArCH2), 4.72 (d, 1H, J = 10.7 Hz, ArCH2), 4.61 (t, 2H,
J = 10.5 Hz, ArCH2), 4.39 (d, 1H, J = 9.4 Hz, H-1), 3.75 (d, 2H,
J = 4.5 Hz, H-6a,b), 3.64 (t, 1H, J = 9.0 Hz, H-3), 3.56–3.39 (m, 3H,
H-2, H-4, H-5), 2.23 (s, 3H, SCH3).
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(27)
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Mp203 °C;[
a
]D ꢁ11.2 (c1 CHCl3);dH (300 MHz;CDCl3)7.96–7.88
(m, 10H, Ar-H), 7.60 (t, J = 7.3 Hz, 1H, Ar-H), 7.52–7.17 (m, 21H, Ar-H,
H-2 and H-6 of SPh), 6.86 (d, J = 7.9 Hz, 2H, H-3 and H-5 of SPh), 5.72
(t, J = 9.3 Hz, 1H, H-3), 5.69 (t, J = 9.4 Hz, 1H, H-20), 5.32 (t, J = 9.7 Hz,
1H, H-2), 5.13 (dd, J = 2.8 Hz, J = 10.3 Hz, 1H, H-30), 4.83 (d, J = 9.9 Hz,
1H, H-1), 4.72 (d, J = 7.8 Hz, 1H, H-10), 4.61 (d, J = 10.9 Hz, 1H, H-6a),
4.31 (dd, J = 4.9 Hz, J = 11.9 Hz, 1H, H-6b), 4.18 (m, 3H, H-40, ArCH2),
4.06(t, J = 9.2 Hz1H, H-4), 3.85(m, 1H, H-5), 3.46(t, J = 5.7 Hz, 1H, H-
50), 3.04–2.93 (m, 2H, H-60 a,b), 2.39 (br s, 1H, OH), 2.21 (s, 3H, Ph-
CH3); dC (75.47 MHz; CDCl3) 166.2, 165.9, 165.7, 165.6, 138.9,
138.2, 134.4, 133.7, 133.6, 130.3, 130.2, 130.0, 129.8, 129.5, 129.3,
128.9, 128.3, 128.0, 101.9, 86.2, 78.0, 76.8, 75.2, 74.7, 73.7, 73.5,
70.9, 70.5, 67.8, 67.5, 63.1 and 21.7; MALDI-TOF MS calcd m/z
1059.137, found m/z 1098.385 (M+K+), 1082.365 (M+Na+). Com-
pound 27 upon acetylation (Ac2O/pyridine, 18 h, 27 °C) gave the cor-
responding 40-O-acetate for which the H-40 chemical shift was
0
0
observed at dH 5.49 (d, J3 ,4 = 3.2 Hz).
Acknowledgements
Authors sincerely acknowledge NIPER for the award of Fellow-
ships to K.V.R. and P.R.P., and a summer internship to S.A.
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