methyl D-olivoside | 92007-64-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl D-olivoside
• 英文别名: methyl 2,6-dideoxy-D-arabino-hexopyranoside；(2R,3S,4R)-6-methoxy-2-methyloxane-3,4-diol
• CAS: 92007-64-2
• 化学式: C₇H₁₄O₄
• 分子量: 162.186
• InChiKey: QNKOVWCOVLYPKR-RARXMTEBSA-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 D-olivoside 在 吡啶 、 2,6-二甲基吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 palladium 10% on activated carbon 、 氢气 、 硫脲 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 (2S,6R)-6-[(2S,3S,6S)-6-[(2R,3S,4R,6S)-4-hydroxy-6-methoxy-2-methyloxan-3-yl]oxy-2-methyloxan-3-yl]oxy-2-methyloxan-3-one
  参考文献：
  名称：

  Chemical and biological evaluation of unusual sugars, α-aculosides, as novel Michael acceptors

  摘要：

  在活细胞中发现了一种新颖且选择性的迈克尔受体，α-阿库洛苷，可以与蛋白质中半胱氨酸残基的巯基功能反应。

  DOI：

  10.1039/c4ob01877j
• 作为产物：
  描述：

  甲醇 、 D-olivose 在 硫酸 作用下， 以400 mg的产率得到methyl D-olivoside
  参考文献：
  名称：

  Pedersen, Christian; Jensen, Hanne Stampe, Acta Chemica Scandinavica, 1994, vol. 48, # 3, p. 222 - 227

  摘要：

  DOI：

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。
• Two-step synthesis of C-glycosyl juglones from unprotected sugars: a novel approach to angucycline antibiotics
  作者：Goh Matsuo、Shuichi Matsumura、Kazunobu Toshima

  DOI：10.1039/cc9960002173

  日期：——

  The two-steps synthesis of C-glycosyl juglones, versatile synthetic intermediates for angucycline antibiotics, has been developed by the C-glycosidation of naphthalene-1,5-diol with an unprotected sugar and the subsequent regioselective photooxygenation of the resultant C-glycosyl naphthalenediol.

  萘-1,5-二醇与未保护的糖进行C-糖基化，随后对得到的C-糖基萘二醇进行位点选择性光氧化，从而合成出两种环己烯类抗生素的多功能合成中间体——C-糖苷萘二醇，该合成过程分为两步。
• c-Arylglycosylation of unprotected free sugar
  作者：Kazunobu Toshima、Goh Matsuo、Toru Ishizuka、Masaya Nakata、Mitsuhiro Kinoshita

  DOI：10.1039/c39920001641

  日期：——

  Highly regio- and stereo-selective C-arylglycosylations of the protected free sugars 1–4, the unprotected methyl glycosides 6–9 and the unprotected free sugars 10 and 11 with 2-naphthol 5 are effectively realized by the combined use of TMSOTf–AgClO4(TMSOTf = trimethylsilyloxytrifluoromethanesulfonate) as a catalytic activator.

  通过 TMSOTf-AgClO4 的组合使用，可以有效实现受保护的游离糖 1-4、未受保护的甲基糖苷 6-9 以及未受保护的游离糖 10 和 11 与 2-萘酚 5 的高度区域和立体选择性 C-芳基糖基化（TMSOTf = 三甲基硅氧基三氟甲磺酸盐）作为催化活化剂。
• An imrpoved practical method for synthesis of aryl C-glycosides from unprotected methyl glycosides and 1-hydroxy sugars
  作者：Kazunobu Toshima、Goh Matsuo、Masaya Nakata

  DOI：10.1039/c39940000997

  日期：——

  Aryl C-glycosidations of the unprotected methyl glycosides 9–12 and the unprotected 1-hydroxy sugars 14 and 15 with 2-naphthol 6 using TMSOTf proceed much more effectively than those of the acylated methyl glycosides 4 and 5; the unprotected methyl glycoside 10 is also smoothly coupled with other phenol and naphthol derivatives 25–27 to give the corresponding unprotected o-hydroxyaryl β-C-glycosides

  使用TMSOTf对未保护的甲基糖苷9-12和未保护的1-羟基糖14和15以及2-萘酚6进行芳基C糖基化作用比酰化的甲基糖苷4和5更为有效。未保护的甲基糖苷10还可与其他苯酚和萘酚衍生物25-27平滑偶联，从而以高收率获得相应的未保护的邻羟基芳基β- C-糖苷（TMSOTf =三甲基甲硅烷氧基三氟甲磺酸酯）。
• Aryl C-glycosylation using an ionic liquid containing a protic acid
  作者：Chigusa Yamada、Kaname Sasaki、Shuichi Matsumura、Kazunobu Toshima

  DOI：10.1016/j.tetlet.2007.04.077

  日期：2007.6

  Aryl C-glycosylation of several glycosyl donors, including unprotected sugars, with phenol and naphthol derivatives in an ionic liquid containing a protic acid proceeded effectively and stereoselectively to give the corresponding aryl C-glycosides in good to high yields. Because the ionic liquid was nonvolatile, the reaction could be carried out under reduced pressure; in addition, the ionic liquid could be reused without loss of effectiveness. These features contribute to the significant advantages of this novel aryl C-glycosylation reaction. (c) 2007 Elsevier Ltd. All rights reserved.