methyl 5-C-methoxy-β-D-galactopyranoside | 134039-11-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-C-methoxy-β-D-galactopyranoside
• CAS: 134039-11-5
• 化学式: C₈H₁₆O₇
• 分子量: 224.211
• InChiKey: XSLCRAOLQBOCQI-FMDGEEDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.59
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  108.61
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 5-C-methoxy-β-D-galactopyranoside 在 水 、 氢气 作用下， 生成 L-arabino-hexos-5-ulose
  参考文献：
  名称：

  一种简单的立体定向途径，可制得5-C-烷氧基-D-吡喃半乳糖苷和L-阿拉伯糖-己糖-5-uloses

  摘要：

  可以容易地转化为L-阿拉伯糖-己糖-5-uloses的5-C-烷氧基-β-D-吡喃半乳糖苷可以由β-D-吡喃半乳糖苷在中间体4-脱氧-α的醇溶剂中通过过氧酸氧化制备-L-苏式-hex-4-enopyranosides。

  DOI：

  10.1016/s0040-4039(00)92130-0
• 作为产物：
  描述：

  methyl 3,4-di-O-isopropylidene-β-D-galactopyranoside 在 palladium on activated charcoal 吡啶 、 potassium tert-butylate 、 氢气 、 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 56.5h， 生成 methyl 5-C-methoxy-β-D-galactopyranoside
  参考文献：
  名称：

  Barili, Pier Luigi; Berti, Giancarlo; Catelani, Giorgio, Gazzetta Chimica Italiana, 1992, vol. 122, # 4, p. 135 - 142

  摘要：

  DOI：

文献信息

• The acetonation of methyl 5-C-methoxy-β-d-galactopyranoside1The nomenclature for these bis-glycosides is still somewhat ambiguous, since the introduction of a substituent at C-5, according to the Cahn, Ingold, Prelog rules, may invert its absolute configuration. We have preferred to use the Fischer nomenclature, since it is simpler and directly correlated with the name of the base compound, which undergoes a substitution of a hydrogen atom with a MeO group. This nomenclature has been previously used by us and by other authors, and is reported without change in Chemical Abstract. According to the more recent rules, the name would be methyl (5R)-5-methoxy-α-l-arabino-hexopyranoside.1 with 2,2-dimethoxypropane
  作者：Maria Camilla Bergonzi、Giorgio Catelani、Felicia D’Andrea、Francesco De Rensis

  DOI：10.1016/s0008-6215(98)00211-0

  日期：1998.10

  Abstract The acetonation of methyl 5- C -methoxy- β - d -galactopyranoside ( 1a ), masked bis-glycoside form of l - arabino -hexos-5-ulose, with a large excess of 2,2-dimethoxypropane and catalytic amounts of p -toluenesulfonic acid gives a mixture of five acetonides. The most abundant isolated product was the mixed acetal methyl 6- O -(1–methoxy-1-methylethyl)-3,4- O -isopropylidene-5- C -methoxy-

  摘要甲基5-C-甲氧基-β-d-吡喃半乳糖苷（1a）的乙酰化反应，掩蔽了1-阿拉伯糖-己-5-糖的双糖苷形式，大量过量的2,2-二甲氧基丙烷和催化量的对甲苯磺酸得到五种丙酮化物的混合物。分离出的产物最多的是混合的缩醛甲基6-O-（1-甲氧基-1-甲基乙基）-3,4- O-异亚丙基-5- C-甲氧基-β-d-吡喃半乳糖苷（44％收率）。
• A new route to d-xylo-hexos-5-ulose and some of its selectively protected derivatives from d-galactose
  作者：Pier Lugi Barili、Giancarlo Berti、Giorgio Catelani、Felicia D'Andrea、Francesco De Rensis

  DOI：10.1016/s0040-4020(97)00536-x

  日期：1997.6

  A new approach to D-xylo-hexos-5-ulose, a useful synthetic intermediate, is described, starting from methyl beta-D-galactopyranoside and involving as the key step an epoxidation/methanolysis of 3-O-protected methyl 2,6-di-O-benzyl-4-deoxy-alpha-L-threo-hex-4-enopyranosides, to produce bis-glycosides of the parent dicarbonylic sugar, which can be obtained free or selectively protected through hydrogenolytic and/or hydrolytic procedures. The diastereo- and regioselectivity of the epoxidation and solvolysis steps are investigated and tentatively interpreted, and new products characterized by NMR techniques, (C) 1997 Elsevier Science Ltd.