methyl 2,6-dideoxy-β-D-lyxo-hexopyranoside | 139756-72-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,6-dideoxy-β-D-lyxo-hexopyranoside
• 英文别名: methyl 2,6-dideoxy-β-D-lyxo-pyranoside；1-β-O-methyl-D-digitose；(2R,3R,4R,6R)-6-methoxy-2-methyloxane-3,4-diol
• CAS: 139756-72-2
• 化学式: C₇H₁₄O₄
• 分子量: 162.186
• InChiKey: QNKOVWCOVLYPKR-GBNDHIKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2,6-dideoxy-β-D-lyxo-hexopyranoside 在 吡啶 、 四丁基亚硝酸铵 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 15.5h， 生成 methyl 2,6-dideoxy-β-D-ribo-hexopyranoside
  参考文献：
  名称：

  Binkley, Roger W., Journal of Carbohydrate Chemistry, 1994, vol. 13, # 1, p. 111 - 124

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 2,6-dideoxy-β-D-ribo-hexopyranoside 在 吡啶 、 四丁基亚硝酸铵 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 15.5h， 生成 methyl 2,6-dideoxy-β-D-lyxo-hexopyranoside
  参考文献：
  名称：

  Binkley, Roger W., Journal of Carbohydrate Chemistry, 1994, vol. 13, # 1, p. 111 - 124

  摘要：

  DOI：

文献信息

• UCH9, a New Antitumor Antibiotic Produced byStreptomyces. II. Structure Elucidation of UCH9 by Mass and NMR Spectroscopy.
  作者：RITSUKO KATAHIRA、YOICHI UOSAKI、HARUMI OGAWA、YOSHINORI YAMASHITA、HIROFUMI NAKANO、MAYUMI YOSHIDA

  DOI：10.7164/antibiotics.51.267

  日期：——

  The structure of UCH9, which is a novel antitumor agent, was determined by spectroscopic methods. UCH9 consists of an aglycone and five 2, 6-dideoxy sugars (three D-olivoses, one 4-O-methyl-D-olivose and one D-oliose). Four of the five sugars are sequentially connected through a β1→3 linkage (olivose-1→3-4-O-methyl-olivose-1→3-oliose-1→3-olivose). On the basis of the results of spectroscopic analysis, it was found that UCH9 belongs to the aureolic acid family of antibiotics. The structure of UCH9 is unique in that mono- and tetrasaccharide moieties, and a long hydrophobic side chain (sec-butyl group) are attached to the aglycone, while di- and trisaccharide moieties and a methyl or a hydrogen are attached in the case of the known aureolic acid analogs. It is known that aureolic acid analogs form a dimer in the presence of Mg2+. NMR, FAB-MS and atomic absorption analysis revealed that UCH9 isolated from Streptomyces also forms a dimer, containing one equivalent molar Mg2+

  UCH9的结构是一种新型抗肿瘤剂，通过光谱方法确定。UCH9由一个非糖部分和五种2,6-二脱氧糖组成（包括三个D-橄榄糖、一个4-O-甲基-D-橄榄糖和一个D-橄榄糖）。五种糖中有四种通过β1→3连接依次相连（橄榄糖-1→3-4-O-甲基-橄榄糖-1→3-橄榄糖-1→3-橄榄糖）。根据光谱分析的结果，发现UCH9属于金黄色酸类抗生素。UCH9的结构独特，因为它的非糖部分连接了单糖和四糖基团，以及一个长的疏水性侧链（叔丁基），而已知的金黄色酸类类似物则连接了二糖和三糖基团以及一个甲基或氢。已知金黄色酸类类似物在存在Mg2+的情况下会形成二聚体。NMR、FAB-MS和原子吸收分析显示，从放线菌中分离的UCH9也形成了一个含有一个当量摩尔的Mg2+的二聚体。
• Synthesis of 2,6-dideoxy-4-S-methyl-4-thio-d-ribo-hexopyranose, a component of the esperamicin oligosaccharide
  作者：François-Yves Dupradeau、Jacques Prandi、Jean-Marie Beau

  DOI：10.1016/0040-4020(95)00059-h

  日期：1995.3

  Two synthetic approaches to 2,6-dideoxy-4-S-methyl-4-thio-D-ribo pyranose, a component of the oligosaccharide of esperamicins are described. An asymmetric synthesis, starting from the propargylic alcohol dimer, relies on the Sharpless asymmetric epoxidation and the regioselective opening of epoxy alcohols. The other synthesis is based on stereocontrolled transformations of a readily available sugar precursor, D-galactose.
• Intramolecular reactions of carbohydrate triflates
  作者：Roger W. Binkley

  DOI：10.1021/jo00034a030

  日期：1992.4

  Each of the four possible methyl 2,6-dideoxy-beta-D-hexopyranosides (3-6) was treated with an equivalent amount of triflic anhydride in the presence of 2,6-di-tert-butyl-4-methylpyridine (7). The ribo isomer 3 produced both the 3-O-triflyl (8, 15%) and the 4-O-triflyl (9, 73%) derivatives while the lyxo isomer 4 gave only the 3-O-triflyl compound (11, 84%). Upon heating, the triflate 8 lost the elements of triflic acid to form methyl 2,3,6-trideoxy-beta-D-glycero-hexopyranosid-4-ulose (23, 72%), while 9 experienced ring contraction involving the pyranoid ring oxygen to form methyl 3,5-anhydro-2,6-dideoxy-beta-D-xylo-hexofuranoside (20, 54%). Compound 11 produced methyl 3-C-aldehydo-2,5-dideoxy-beta-D-threo-pentofuranoside (13, 65%). Upon reaction with triflic anhydride, methyl 2,6-dideoxy-beta-D-arabino- and -xylo-hexopyranosides (5 and 6, respectively) generated hydroxy triflates which were not isolated due to their further reaction below room temperature. Compound 5 produced aldehyde 13 (54%) while reaction of 6 gave methyl 3,4-anhydro-2,6-dideoxy-beta-D-lyxo- and -ribo-hexopyranosides [15 (48%) and 16 (24%), respectively]. The mechanisms for these reactions are discussed and the reactivity of the hydroxy triflates is compared to that of related carbohydrate derivatives.
• Binkley, Roger W., Journal of Carbohydrate Chemistry, 1994, vol. 13, # 1, p. 111 - 124
  作者：Binkley, Roger W.

  DOI：——

  日期：——