(1S)-(1(OH),2,4,5/1,3)-1-C-(Hydroxymethyl)-1,2,3,4,5-cyclohexanepentol | 115250-26-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S)-(1(OH),2,4,5/1,3)-1-C-(Hydroxymethyl)-1,2,3,4,5-cyclohexanepentol
• 英文别名: (1S,2S,3R,4S,5S)-1-(hydroxymethyl)cyclohexane-1,2,3,4,5-pentol
• CAS: 115250-26-5
• 化学式: C₇H₁₄O₆
• 分子量: 194.185
• InChiKey: BGUDMWRLGIINNY-ZYNSJIGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.44
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  121.38
• 氢给体数：
  6.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  (3S,4S,5S,6R)-2,2-二氯-3-羟基-4,5,6-三(苯基甲氧基)-3-[(苯基甲氧基)甲基]环己酮 在 钯 甲醇 、 sodium tetrahydroborate 、 甲酸 、 偶氮二异丁腈 、 三正丁基氢锡 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 2.5h， 生成 (1S)-(1(OH),2,4,5/1,3)-1-C-(Hydroxymethyl)-1,2,3,4,5-cyclohexanepentol
  参考文献：
  名称：

  Synthesis of a branched-chain inosose derivative, a versatile synthon of N-substituted valiolamine derivatives from D-glucose

  摘要：

  The synthesis of (1S)-(1(OH)-2,4/1,3)-2,3,4-tri-O-benzyl-1-C-[(benzyloxy)methyl]-5-oxo-1,2,3,4-cyclohexanetetrol (7), which is an important synthon for the synthesis of valiolamine (8) 2 and its N-substituted derivatives such as AO-128 (9)3 having strong alpha-D-glucosidase inhibitory activity, is described. This branched-chain inosose derivative 7 has been prepared from the D-glucono-1,5-lactone derivative 2 which is readily available from D-glucose (1). The key step in the synthesis involves the stereospecific intramolecular carbocyclic ring, closure of the 1-deoxy-2, 6-heptodiulose derivatives 5a and 5b obtained by the oxidation of 2,3,4,6-tetra-O-benzyl-1-C-[bis-(methylthio)methyl]-D-glucitol (4a) and 2,3,4,6-tetra-O-benzyl-1-C-(dichloromethyl)-D-glucitol (4b). The resulting branched-chain bis(methylthio)inosose derivative 6a and dichloroinosose derivative 6b have been converted to the desired branched-chain inosose derivative 7 by desulfurization of 6a and dechlorination of 6b.

  DOI：

  10.1021/jo00039a025