methyl 2-deoxy-α-D-threo-pentopyranoside | 55700-61-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-deoxy-α-D-threo-pentopyranoside
• 英文别名: (3R,4R,6S)-6-methoxyoxane-3,4-diol
• CAS: 55700-61-3
• 化学式: C₆H₁₂O₄
• 分子量: 148.159
• InChiKey: CYLGOSOYSUHPCY-PBXRRBTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  10
• 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：

  乙酸酐 、 methyl 2-deoxy-α-D-threo-pentopyranoside 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 反应 18.0h， 以83%的产率得到methyl 2-deoxy-α-D-threo-pentopyranoside 3,4-diacetate
  参考文献：
  名称：

  Indium-mediated allylation of aldehydes: A convenient route to 2-deoxy and 2,6-dideoxy carbohydrates

  摘要：

  The allylation of protected polyhydroxy aldehydes 1 and 14 has been achieved by indium metal with ultrasound promotion generating the diastereomeric pair of homoallylic polyols 3, 4 and 16, 17 respectively with moderate to good stereoselectivity. Pursuing this allylation strategy with the corresponding deprotected polyhydroxy aldehydes led to the same pair of homoallylic polyols but with a quite different ratio of the diastereomers generated. The polyols were further transformed to 2-deoxy (5 and 6) and 2,6-dideoxy (18 and 19) carbohydrates by ozonolysis.

  DOI：

  10.1016/s0040-4020(01)80790-0
• 作为产物：
  描述：

  (3R,4R)-6-methoxyoxane-3,4-diol 在 sodium methylate 作用下， 以 吡啶 、 甲醇 为溶剂， 生成 methyl 2-deoxy-α-D-threo-pentopyranoside
  参考文献：
  名称：

  Medonos, Ivan; Kocikova, Veroslava; Stanek, Jan, Collection of Czechoslovak Chemical Communications, 1986, vol. 51, # 8, p. 1671 - 1677

  摘要：

  DOI：

文献信息

• Haque, Md. Ekramul; Kikuchi, Tohoru; Kanemitsu, Kimihiro, Chemical and pharmaceutical bulletin, 1986, vol. 34, # 1, p. 430 - 433
  作者：Haque, Md. Ekramul、Kikuchi, Tohoru、Kanemitsu, Kimihiro、Tsuda, Yoshisuke

  DOI：——

  日期：——
• Indium-mediated allylation of aldehydes: A convenient route to 2-deoxy and 2,6-dideoxy carbohydrates
  作者：Wolfgang H. Binder、Reinhard H. Prenner、Walther Schmid

  DOI：10.1016/s0040-4020(01)80790-0

  日期：1994.1

  The allylation of protected polyhydroxy aldehydes 1 and 14 has been achieved by indium metal with ultrasound promotion generating the diastereomeric pair of homoallylic polyols 3, 4 and 16, 17 respectively with moderate to good stereoselectivity. Pursuing this allylation strategy with the corresponding deprotected polyhydroxy aldehydes led to the same pair of homoallylic polyols but with a quite different ratio of the diastereomers generated. The polyols were further transformed to 2-deoxy (5 and 6) and 2,6-dideoxy (18 and 19) carbohydrates by ozonolysis.
• Medonos, Ivan; Kocikova, Veroslava; Stanek, Jan, Collection of Czechoslovak Chemical Communications, 1986, vol. 51, # 8, p. 1671 - 1677
  作者：Medonos, Ivan、Kocikova, Veroslava、Stanek, Jan、Zobacova, Alena、Jary, Jiri

  DOI：——

  日期：——