ethyl 6-O-benzyl-2,3-dideoxy-4-O-methanesulfonyl-α-D-threo-hexopyranoside | 270088-70-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 6-O-benzyl-2,3-dideoxy-4-O-methanesulfonyl-α-D-threo-hexopyranoside
• 英文别名: [(2R,3R,6S)-6-ethoxy-2-(phenylmethoxymethyl)oxan-3-yl] methanesulfonate
• CAS: 270088-70-5
• 化学式: C₁₆H₂₄O₆S
• 分子量: 344.429
• InChiKey: DGRMMRNNWYDMAF-OAGGEKHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  79.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 6-O-benzyl-2,3-dideoxy-4-O-methanesulfonyl-α-D-threo-hexopyranoside 在 palladium on activated charcoal sodium azide 、 氢气 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 1-(2-chloroethyl)-3-[(2S,3S,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：

  ethyl 6-O-benzyl-2,3-dideoxy-4-O-methanesulfonyl-α-D-erythro-hexopyranoside 在 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 ethyl 6-O-benzyl-2,3-dideoxy-4-O-methanesulfonyl-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