(1R)-(1,3/2)-3-hydroxymethyl-5-cyclohexene-1,2-diol | 143058-81-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R)-(1,3/2)-3-hydroxymethyl-5-cyclohexene-1,2-diol
• 英文别名: (1R,2R,3R)-3-(hydroxymethyl)cyclohex-5-ene-1,2-diol；5a-carba-D-glucal；(1~{r},2~{r},6~{r})-6-(Hydroxymethyl)cyclohex-3-Ene-1,2-Diol；(1R,2R,6R)-6-(hydroxymethyl)cyclohex-3-ene-1,2-diol
• CAS: 143058-81-5
• 化学式: C₇H₁₂O₃
• 分子量: 144.17
• InChiKey: JIULRVIFQNXLCR-FSDSQADBSA-N

物化性质

• 沸点：
  274.2±40.0 °C(Predicted)
• 密度：
  1.283±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R)-(1,3/2)-3-hydroxymethyl-5-cyclohexene-1,2-diol 在 吡啶 作用下， 反应 7.0h， 生成 3,6-di-O-benzoyl-5a-carba-4-O-mesyl-D-glucal
  参考文献：
  名称：

  Tsunoda, Hidetoshi; Ogawa, Seiichiro, Liebigs Annalen der Chemie, 1994, # 2, p. 103 - 108

  摘要：

  DOI：
• 作为产物：
  描述：

  (1S,2R,3R)-2,3-diacetoxy-4-cyclohexene-1-carboxylic acid 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (1R)-(1,3/2)-3-hydroxymethyl-5-cyclohexene-1,2-diol
  参考文献：
  名称：

  Preparation of building blocks for carba-oligosaccharides related to cell-surface glycans

  摘要：

  DOI：

  10.1016/s0008-6215(00)90491-9

文献信息

• Synthesis of 2-O-(2-acetamido-2-deoxy-β-spD- glucopyranosyl)-5a-carba-α-spD-mannopyranose, and 5a-carba-2O- and 3,6-di-O-(α-d-mannopyranosyl)- α-spD-mannopyranoses
  作者：Seiichiro Ogawa、Kenji Nishi

  DOI：10.1016/s0008-6215(00)90484-1

  日期：1992.5

  Protected derivatives of the title carba-trisaccharide 1, and carba-disaccharides 4 and 6 have been synthesised by conventional glycosylation of the precursors 8, 9, or 22 of 5a-carba-alpha-D-mannopyranose with sugar halides. These are carba-sugar analogues of the oligosaccharide chains frequently occurring as structural units in biologically important glycoconjugates, and could be utilised as the building blocks for construction of higher carba-oligosaccharides of biological interest.
• Tsunoda, Hidetoshi; Ogawa, Seiichiro, Liebigs Annalen, 1995, # 2, p. 267 - 278
  作者：Tsunoda, Hidetoshi、Ogawa, Seiichiro

  DOI：——

  日期：——
• Synthesis and enzyme-inhibitory activity of methyl acarviosin analogues having the α- manno configuration
  作者：Seiichiro Ogawa、Yoshikazu Nakamura

  DOI：10.1016/0008-6215(92)84056-x

  日期：1992.3

  Two methyl acarviosin analogues 3a and 4a, having the alpha-manno configuration, and their dihydro derivatives 6a and 7a were synthesised by coupling the protected pseudo-sugar epoxides with methyl 4-amino-4-deoxy- and -4,6-dideoxy-alpha-D-mannopyranoside. Similarly, two analogous compounds 5a and 8a composed of the 1,6-anhydro-beta-D-mannopyranose residues were prepared. Compound 7a showed mild inhibitory activity against Jack bean alpha-D-mannosidase, and 3a was a moderate inhibitor of both alpha-D-mannosidase and yeast alpha-D-glucosidase.