一些氨基糖在结构上与由6-脱氧-2,3-O-异亚丙基-α-D-吡喃木糖-5-酮糖甲酯和2,3-O-异亚丙基-α-D-呋喃戊二醛-1,4-呋喃糖苷甲酯制备的6-脱氧甘露基里霉素前体相关。

Some amino sugars structurally related to 6-deoxymannojirimycin precursors prepared from methyl 6-deoxy-2,3-O-isopropylidene-alpha-D-lyxo-hexofuranosid-5-ulose and methyl 2,3-O-isopropylidene-alpha-D-lyxo-pentodialdo-1,4-furanoside.

作者信息

Micová Júlia, Steiner Bohumil, Koós Miroslav, Langer Vratislav, Durík Marián, Gyepesová Dalma, Smrcok L'ubomír

机构信息

Institute of Chemistry, Slovak Academy of Sciences, Dúbravská cesta 9, SK-84238 Bratislava, Slovak Republic.

出版信息

Carbohydr Res. 2002 Apr 17;337(8):663-72. doi: 10.1016/s0008-6215(02)00058-7.

DOI:10.1016/s0008-6215(02)00058-7

PMID:11950463

Abstract

Methyl (5S)-5-C-amino-5-cyano-5-deoxy-2,3-O-isopropylidene-alpha-D-lyxofuranoside has been synthesised from methyl 2,3-O-isopropylidene-alpha-D-lyxo-pentodialdo-1,4-furanoside, applying the Strecker synthesis. Analogously, methyl (5S) and (5R)-5-C-amino-5-cyano-5,6-dideoxy-2,3-O-isopropylidene-alpha-D-lyxo-hexofuranosides were prepared from methyl 6-deoxy-2,3-O-isopropylidene-alpha-D-lyxo-hexofuranosid-5-ulose. The 5-S configuration was unambiguously determined by single-crystal X-ray diffraction analysis of corresponding N-acetyl derivatives. Conformations of five-membered rings are discussed. The conversion of N-acetylated amino nitriles to N-acetylamino acid ethyl ester and amide, respectively, is also described.

摘要

(5S)-5-C-氨基-5-氰基-5-脱氧-2,3-O-异亚丙基-α-D-来苏呋喃糖甲苷已由2,3-O-异亚丙基-α-D-来苏戊二醛-1,4-呋喃糖甲苷通过施特雷克合成法合成。类似地，(5S)和(5R)-5-C-氨基-5-氰基-5,6-二脱氧-2,3-O-异亚丙基-α-D-来苏己呋喃糖甲苷由6-脱氧-2,3-O-异亚丙基-α-D-来苏己呋喃糖-5-酮糖甲苷制备。通过相应的N-乙酰基衍生物的单晶X射线衍射分析明确确定了5-S构型。讨论了五元环的构象。还描述了N-乙酰化氨基腈分别转化为N-乙酰基氨基酸乙酯和酰胺的过程。