methyl 3,6-dideoxy-α-D-xylo-hexopyranoside | 6109-60-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,6-dideoxy-α-D-xylo-hexopyranoside
• 英文别名: methyl α-D-xylo-3,6-dideoxy-hexopyranoside；methyl α-abequopyranoside；(2S,3R,5R,6R)-2-methoxy-6-methyloxane-3,5-diol
• CAS: 6109-60-0
• 化学式: C₇H₁₄O₄
• 分子量: 162.186
• InChiKey: DRIBCYZSKHETPK-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 3,6-dideoxy-α-D-xylo-hexopyranoside 生成 3,6-Didesoxy-D-xylo-hexit (1,4-Didesoxy-L-xylo-hexit)
  参考文献：
  名称：

  GAREGG, PER J.;LINDBERG, BENGT;KONRADSSON, PETER;KVARNSTROM, INGEMAR, CARBOHYDR. RES., 176,(1988) N 1, 145-148

  摘要：

  DOI：
• 作为产物：
  描述：

  Α-D-乳酸吡喃糖苷甲酯 在 吡啶 、 sodium hydroxide 、 双氧水 、 三乙基硼氢化锂 作用下， 以 甲醇 为溶剂， 反应 23.0h， 生成 methyl 3,6-dideoxy-α-D-xylo-hexopyranoside
  参考文献：
  名称：

  Reactions of p-toluenesulfonates with lithium triethylborohydride. Visible and hidden rearrangements

  摘要：

  DOI：

  10.1021/jo00350a044

文献信息

• Oligosaccharide recognition by antibodies: Synthesis and evaluation of talose oligosaccharide analogues
  作者：T L Lowary、E Eichler、D R Bundle

  DOI：10.1139/v02-118

  日期：2002.8.1

  A series of monosaccharide (4–6), disaccharide (3,7–12), and trisaccharide (13–15) analogs of the native ligand 2, which fills the binding site of monoclonal antibody Se 155.4, have been synthesized and their bioactivity measured by solid- and solution-phase assays. The syntheses of disaccharide analogs sought to replace galactose by various alkyl groups at the O-2 position of mannose. The activity of one of these O-2 alkyl analogs was 75% of that observed for the trisaccharide and points to only weak net bonding between the solvent exposed galactose residue and the antibody binding site. The synthesis of talose analogs 13 and 14, where the mannose or galactose residues of 2 were replaced by talose produced ligands with activities from one-third to one-half of that seen for the native ligand 2. These activity changes did not exhibit discernable correlations with the ability of talose to disrupt water of solvation.Key words: abequose, 3,6-dideoxy-D-xylo-hexose, talose disaccharide and trisaccharide, antibody oligosaccharide interactions, molecular recognition of carbohydrates, water in antibody complexes, Salmonella LPS, monoclonal antibody Se 155.4, bacterial O-antigen.

  一系列单糖（4-6）、二糖（3、7-12）和三糖（13-15）类似物已经合成，它们是原生配体2的类似物，填充了单克隆抗体Se 155.4的结合位点，并通过固相和溶液相测定了它们的生物活性。二糖类似物的合成旨在将半乳糖替换为甘露糖的O-2位置的各种烷基。其中一种O-2烷基类似物的活性为观察到的三糖活性的75%，表明溶剂暴露的半乳糖残基与抗体结合位点之间只有弱的净键合。通过将原生配体2的甘露糖残基替换为甜菜糖合成了甜菜糖类似物13和14，这些配体的活性为原生配体2的三分之一到一半。这些活性变化与甜菜糖破坏溶剂水的能力之间没有明显的相关性。关键词：阿贝酮，3,6-二去氧-D-木糖-己糖，甜菜糖二糖和三糖，抗体寡糖相互作用，碳水化合物的分子识别，抗体复合物中的水，沙门氏菌LPS，单克隆抗体Se 155.4，细菌O抗原。
• Marek, Miroslav; Jary, Jiri, Collection of Czechoslovak Chemical Communications, 1980, vol. 45, # 11, p. 2979 - 2984
  作者：Marek, Miroslav、Jary, Jiri

  DOI：——

  日期：——
• Baer, Hans H.; Astles, David J.; Chin, Ho-chi, Canadian Journal of Chemistry, 1985, vol. 63, p. 432 - 439
  作者：Baer, Hans H.、Astles, David J.、Chin, Ho-chi、Siemsen, Lisa

  DOI：——

  日期：——
• Synthesis of a Pentasaccharide Epitope for the Investigation of Carbohydrate-Protein Interactions
  作者：Todd L. Lowary、Eva Eichler、David R. Bundle

  DOI：10.1021/jo00127a043

  日期：1995.11

  Pyranose residues of a polysaccharide that are not involved in the principal sugar-protein antibody combining site, filled by trisaccharide 1, cause a 50-fold reduction in intrinsic affinity. The antibody is crystallographically characterized, and the residue responsible for the lost binding energy has been identified as the terminal disaccharide Rha-->Gal of pentasaccharide 5. This disaccharide segment of 5 may avoid protein contact by adopting the ''anti'' conformer about the preceding Man-Rha glycosidic linkage. Monosaccharide thioglycoside synthons 6-9 were used in NIS-promoted glycosylations to synthesize the pentasaccharide as a glycoside that was suitable for binding and solution conformational studies. Disaccharide 29 was obtained upon the addition of rhamnose building unit 6 to the (trimethylsilyl)ethyl galactopyranoside 10 followed by protecting group manipulation. The sequential addition of 7-9 to 29 afforded the pentasaccharide derivative 35 bearing a 2-O-benzoate group suited for subsequent 1,2-trans-glycoside synthesis following its conversion to a glycosyl imidate. In order to preserve the integrity of the 3,6-dideoxyhexopyranosyl glycosidic bond during cleavage of the (trimethylsilyl)ethyl group leading to the imidate 39, it was essential to convert the benzylated pentasaccharide target 35 into its fully acylated derivative 37. Pentasaccharide 5 was obtained by transesterification of the protected glycoside 40 formed via 39. Qualitative NOE measurements suggest a predominant solution conformation for 5 that cannot be adopted in the bound state due to protein-oligosaccharide clashes at the periphery of the binding site.
• Preparation of methyl 3,6-dideoxy-α-d-xylo-hexopyranoside (methyl α-abequoside) and its α-l-lyxo isomer by reduction of epoxides with lithium triethylborohydride
  作者：Hans H. Baer、David J. Astles

  DOI：10.1016/0008-6215(84)85395-1

  日期：1984.3