methyl 4-amino-2,4-dideoxy-β-D-arabino-hexopyranoside | 270088-63-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-amino-2,4-dideoxy-β-D-arabino-hexopyranoside
• 英文别名: (2S,3S,4R,6R)-3-amino-2-(hydroxymethyl)-6-methoxyoxan-4-ol
• CAS: 270088-63-6
• 化学式: C₇H₁₅NO₄
• 分子量: 177.2
• InChiKey: CGJLGDMYUYGQCJ-GBNDHIKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  84.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2-chloroethyl)nitrosocarbamic acid 2,4,5-trichlorophenyl ester 、 methyl 4-amino-2,4-dideoxy-β-D-arabino-hexopyranoside 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-(2-chloroethyl)-3-[(2S,3S,4R,6R)-4-hydroxy-2-(hydroxymethyl)-6-methoxyoxan-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：

  1,6-脱水-2-脱氧-2-碘-D-吡喃葡萄糖 在 偶氮二异丁腈 吡啶 、 sodium azide 、 Amberlite R₁₅ (H)+ 、 三正丁基氢锡 、 sodium methylate 、 氯化铵 作用下， 以 甲醇 、 乙醇 、 氯仿 、 水 、 甲苯 为溶剂， 反应 125.5h， 生成 methyl 4-amino-2,4-dideoxy-β-D-arabino-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.