Volume 19, Issue 2
Natural Products
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ChemInform Abstract: Regioselective One-Pot Approach to Aminodeoxy Sugars via Aminosilanes.

A. MALIK

A. MALIK

H. E. J. Res. Inst. Chem., Univ., Karachi-32, Pakistan

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N. KAZMI

N. KAZMI

H. E. J. Res. Inst. Chem., Univ., Karachi-32, Pakistan

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A. Q. KHAN

A. Q. KHAN

H. E. J. Res. Inst. Chem., Univ., Karachi-32, Pakistan

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Z. AHMAD

Z. AHMAD

H. E. J. Res. Inst. Chem., Univ., Karachi-32, Pakistan

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First published: January 12, 1988

Abstract

The 2,3-anhydro-α-D-allopyranoside (I) is converted to the aminodeoxy- α-D-glucopyranoside derivative (III) by regioselective trans-diaxial cleavage of the epoxide ring with N,N-(diethyl)trimethylsilylamine (II) in the presence of AlCl3.

ChemInform Abstract

The 2,3-anhydro-α-D-allopyranoside (I) is converted to the aminodeoxy- α-D-glucopyranoside derivative (III) by regioselective trans-diaxial cleavage of the epoxide ring with N,N-(diethyl)trimethylsilylamine (II) in the presence of AlCl3. Four further examples of analogous reactions are described in the original paper. (Mechanism).

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