4-O-乙酰基-3-叠氮基-2,3,6-三脱氧-6-碘-α-D-阿拉伯己吡喃糖苷甲酯的合成、晶体结构及高分辨率核磁共振光谱

Synthesis, the crystal structure, and high-resolution NMR spectroscopy of methyl 4-O-acetyl-3-azido-2,3,6-trideoxy-6-iodo-alpha-D-arabino-hexopyranoside.

作者信息

Dabrowska Aleksandra, Konitz Antoni, Smiatacz Zygfryd

机构信息

Department of Chemistry, University of Gdańsk, 18/19 Sobieski Strasse, PL-80-952 Gdańsk, Poland.

出版信息

Carbohydr Res. 2002 Feb 5;337(2):175-81. doi: 10.1016/s0008-6215(01)00302-0.

DOI:10.1016/s0008-6215(01)00302-0

PMID:11814450

Abstract

Selective tosylation followed by acetylation of methyl 3-azido-2,3-dideoxy-alpha-D-arabino-hexopyranoside (1) in pyridine at room temperature affords a mixture of methyl 4-O-acetyl-3-azido-2,3-dideoxy-6-di-O-p-tolylsulfonyl-alpha-D-arabino-hexopyranoside (4) and methyl 3-azido-2,3-dideoxy-4,6-di-O-p-tolylsulfonyl-alpha-D-arabino-hexopyranoside (3). Compound 4 undergoes nucleophilic displacement with sodium iodide in acetic anhydride to give methyl 4-O-acetyl-3-azido-2,3,6-trideoxy-6-iodo-alpha-D-arabino-hexopyranoside (7), whose crystal structure and (1H) and (13)C NMR data are reported. This compound adopts the 4C(1) conformation.

摘要

在室温下，于吡啶中对3-叠氮基-2,3-二脱氧-α-D-阿拉伯己吡喃糖苷（1）进行选择性甲苯磺酰化，随后乙酰化，得到4-O-乙酰基-3-叠氮基-2,3-二脱氧-6-二-O-对甲苯磺酰基-α-D-阿拉伯己吡喃糖苷（4）和3-叠氮基-2,3-二脱氧-4,6-二-O-对甲苯磺酰基-α-D-阿拉伯己吡喃糖苷（3）的混合物。化合物4在乙酸酐中与碘化钠发生亲核取代反应，生成4-O-乙酰基-3-叠氮基-2,3,6-三脱氧-6-碘-α-D-阿拉伯己吡喃糖苷（7），报道了其晶体结构以及（1H）和（13C）核磁共振数据。该化合物呈4C（1）构象。