ethyl 4-amino-2,3,4-trideoxy-α-D-threo-hexopyranoside | 88066-24-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 4-amino-2,3,4-trideoxy-α-D-threo-hexopyranoside
• 英文别名: [(2S,3R,6S)-3-amino-6-ethoxyoxan-2-yl]methanol
• CAS: 88066-24-4
• 化学式: C₈H₁₇NO₃
• 分子量: 175.228
• InChiKey: WJNQWWXBMCYGBP-PRJMDXOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  64.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2-chloroethyl)nitrosocarbamic acid 2,4,5-trichlorophenyl ester 、 ethyl 4-amino-2,3,4-trideoxy-α-D-threo-hexopyranoside 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-(2-chloroethyl)-3-[(2S,3R,6S)-6-ethoxy-2-(hydroxymethyl)oxan-3-yl]-1-nitrosourea
  参考文献：
  名称：

  Synthesis and antitumour activity of a new series of nitrosoureido sugars

  摘要：

  New nitrosoureido derivatives of di- or tri-deoxy-sugars have been synthesized. Very potent antitumour activity against L1210 leukaemia was exhibited by the compounds derived from methyl 3-amino-3,4-dideoxy-beta- and alpha- and 4-amino-2,4-dideoxy-beta- and alpha-D-arabino-hexopyranosides; 24, 26, 28 and 29, respectively. in further evaluation against B16 melanocarcinoma bearing mice, only compounds 24 and 26 displayed significant activity. Owing to its lower acute toxicity, methyl 3-[3-(2-chloroethyl)-3-nitrosoureido]-3,4dideoxy-beta-D-arabino-hexopyranoside 24 appeared as the best candidate for preclinical studies. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00114-8
• 作为产物：
  描述：

  (2S,3R,6S)-3-Azido-2-benzyloxymethyl-6-ethoxy-tetrahydro-pyran 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 ethyl 4-amino-2,3,4-trideoxy-α-D-threo-hexopyranoside
  参考文献：
  名称：

  Synthesis and antitumour activity of a new series of nitrosoureido sugars

  摘要：

  New nitrosoureido derivatives of di- or tri-deoxy-sugars have been synthesized. Very potent antitumour activity against L1210 leukaemia was exhibited by the compounds derived from methyl 3-amino-3,4-dideoxy-beta- and alpha- and 4-amino-2,4-dideoxy-beta- and alpha-D-arabino-hexopyranosides; 24, 26, 28 and 29, respectively. in further evaluation against B16 melanocarcinoma bearing mice, only compounds 24 and 26 displayed significant activity. Owing to its lower acute toxicity, methyl 3-[3-(2-chloroethyl)-3-nitrosoureido]-3,4dideoxy-beta-D-arabino-hexopyranoside 24 appeared as the best candidate for preclinical studies. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(00)00114-8

文献信息

• Synthesis and antitumour activity of a new series of nitrosoureido sugars
  作者：C Monneret

  DOI：10.1016/s0223-5234(00)00114-8

  日期：2000.1

  New nitrosoureido derivatives of di- or tri-deoxy-sugars have been synthesized. Very potent antitumour activity against L1210 leukaemia was exhibited by the compounds derived from methyl 3-amino-3,4-dideoxy-beta- and alpha- and 4-amino-2,4-dideoxy-beta- and alpha-D-arabino-hexopyranosides; 24, 26, 28 and 29, respectively. in further evaluation against B16 melanocarcinoma bearing mice, only compounds 24 and 26 displayed significant activity. Owing to its lower acute toxicity, methyl 3-[3-(2-chloroethyl)-3-nitrosoureido]-3,4dideoxy-beta-D-arabino-hexopyranoside 24 appeared as the best candidate for preclinical studies. (C) 2000 Editions scientifiques et medicales Elsevier SAS.