Methyl 2,6-dideoxy-β-D-arabino-hexopyranoside | 17676-16-3

• 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-arabino-hexopyranoside
• 英文别名: (2R,3S,4R,6R)-6-methoxy-2-methyloxane-3,4-diol
• CAS: 17676-16-3
• 化学式: C₇H₁₄O₄
• 分子量: 162.186
• InChiKey: QNKOVWCOVLYPKR-DBRKOABJSA-N

物化性质

• 熔点：
  84 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  273.7±40.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

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-arabino-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 31.0h， 生成 Methyl 3,4-di-O-benzoyl-2,6-dideoxy-β-D-arabino-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：

  甲基 Β-D-吡喃葡萄糖苷 在 palladium on activated charcoal 吡啶 、 六甲基磷酰三胺 、 N-溴代丁二酰亚胺(NBS) 、 水 、 氢气 、 sodium methylate 、 三乙胺 、 三苯基膦 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 68.58h， 生成 Methyl 2,6-dideoxy-β-D-arabino-hexopyranoside
  参考文献：
  名称：

  Synthesis of methyl 2,6-dideoxy-β-D-arabino-, 3,6-dideoxy-β-D-ribo-, and 4,6-dideoxy-β-D-xylo-hexopyranosides

  摘要：

  DOI：

  10.1007/bf00629918

文献信息

• The preparation of some bromodeoxy- and deoxy-hexoses from bromodeoxyaldonic acids
  作者：Klaus Bock、Inge Lundt、Christian Pedersen

  DOI：10.1016/s0008-6215(00)85607-4

  日期：1981.3

  Abstract The reduction of 2,6-dibromo-2,6-dideoxy- D -mannono- and 2,6-dibromo-2,6-dideoxy- D -glucono-1,4-lactone with sodium borohydride affords 2,6-dibromo-2,6-dideoxy- D -mannose and 2,6-dibromo-2,6-dideoxy- D -glucose, respectively, which may be isolated as their acetates. Similarly, 2-bromo-2,6-dideoxy- L- -glucono-1,4-lactone yields 2-bromo-2,6-dideoxy- L -glucose. Hydrogenolysis of 2,6-dibromo-2

  摘要用硼氢化钠还原2,6-二溴-2,6-二脱氧-D-甘露糖醛和2,6-二溴-2,6-二脱氧-D-葡糖醛-1,4-内酯可得到2,6-二溴-2,6-二脱氧-D-甘露糖和2,6-二溴-2,6-二脱氧-D-葡萄糖，它们可以作为乙酸盐被分离出来。类似地，2-溴-2,6-二脱氧-L-葡萄糖基-1,4-内酯产生2-溴-2,6-二脱氧-L-葡萄糖。2,6-二溴-2,6-二脱氧-D-甘露聚糖-1,4-内酯的氢解反应产生6-溴-2,6-二脱氧-D-阿拉伯糖-己酮-1,4-内酯，随后为2 ，6-二脱氧-D-阿拉伯糖-己烯-1，4-内酯。用双（1,2-二甲基丙基）硼烷还原后者可得到2,6-二脱氧-D-阿拉伯糖基己糖，可将其转化为甲基2,6-二脱氧-3,4-二-O-p-硝基苯甲酰基-D-阿拉伯糖基-己吡喃糖苷。
• 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。
• Syntheses of β-2-deoxy-D-glycosides assisted by glycosidases
  作者：Jean-Michel Petit、Françoise Paquet、Jean-Marie Beau

  DOI：10.1016/0040-4039(91)80769-3

  日期：1991.10

  Enzyme-catalyzed preparation of β-2-deoxy-D-glucosides and galactosides including disaccharides has been achieved using the corresponding glycals as substrates.

  使用相应的糖基作为底物，已经实现了酶催化的β-2-脱氧-D-葡萄糖苷和半乳糖苷（包括二糖）的制备。
• Negative-Ion Mass Spectrometry of Carbohydrates. A Mechanistic Study of the Fragmentation Reactions of Dideoxy Sugars
  作者：Roger W. Binkley、Edith R. Binkley、Shaoming Duan、Michael J. S. Tevesz、Witold Winnik

  DOI：10.1080/07328309608005697

  日期：1996.9

  Hydroxyl group deprotonation of the alpha and beta anomers of methyl 3-O-benzyl-2,6-dideoxy-D-arabino-hexopyranoside (1 and 2) occurs readily in the gas phase to produce the corresponding anions 3 and 4, respectively. Collisionally activated dissociation (CAD) of these anions causes fragmentation reactions that include ring opening, E2 elimination, and decarbonylation. Mechanisms for these reactions are proposed, and these mechanisms are supported by study of partially deuterated analogs of 1 and 2.
• Substrate Flexibility of Vicenisaminyltransferase VinC Involved in the Biosynthesis of Vicenistatin
  作者：Atsushi Minami、Tadashi Eguchi

  DOI：10.1021/ja0685250

  日期：2007.4.1

  A glycosyltransferase VinC is involved in the biosynthesis of antitumor beta-glycoside antibiotic vicenistatin. It catalyzes a glycosyl transfer reaction between dTDP-alpha-D-vicenisamine and vicenilactam. Previous identification of its broad substrate specificity toward various glycosyl acceptors enabled us to explore the potential of VinC for glycodiversification. In vitro study of the substrate specificity toward several dTDP-sugars with vicenilactam established that VinC displayed activities with alpha-anomers of several dTDP-2-deoxy-D-sugars such as mycarose, digitoxose, olivose, and 2-deoxyglucose to afford respective beta-glycosides. Notably, beta-anomers of dTDP-2-deoxy-D-sugars also appeared to be accepted by VinC to form alpha-glycosides. Furthermore, VinC is capable of catalyzing glycosyl transfer reactions from both the alpha-anomer and beta-anomer of dTDP-L-mycarose, respectively, into beta-glycoside and alpha-glycoside. These results indicate that VinC is a unique glycosyltransferase possessing broad substrate specificity. The mechanism of this axially oriented glycosidic bond formation from the equatorially oriented dTDP-sugar might be explained by conformational change of dTDP-sugar to a boat conformation during the glycosyl transfer reaction. To apply these features of VinC for glycodiversification, 22 sets of structurally diverse glycosides were constructed using unnatural glycosyl donors and acceptors.