2-acetamido-2,4-dideoxy-β-D-xylo-hexopyranose

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2-acetamido-2,4-dideoxy-β-D-xylo-hexopyranose
• 英文别名: N-[(2R,3R,4S,6S)-2,4-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• 化学式: C₈H₁₅NO₅
• 分子量: 205.211
• InChiKey: LLRSBEXKLNOWPS-RULNZFCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  99
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苄基-2-乙酰胺基-2-脱氧-Alpha-D-吡喃葡萄糖苷 在 palladium on activated charcoal 吡啶 、 氢氧化钾 、 氢气 、 溶剂黄146 、 N,N'-硫羰基二咪唑 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 20.0 ℃ 、344.74 kPa 条件下， 反应 104.67h， 生成 2-acetamido-2,4-dideoxy-β-D-xylo-hexopyranose
  参考文献：
  名称：

  Synthesis of 4-deoxy analogues of 2-acetamido-2-deoxy-d-glucose and 2-acetamido-2-deoxy-d-xylose and their effects on glycoconjugate biosynthesis

  摘要：

  4-Deoxy analogues of 2-acetamido-2-deoxy-D-glucose and 2-acetamido-2-deoxy-D-xylose were synthesized and evaluated as inhibitors of glycoconjugate biosynthesis. Methyl 2-acetamido-2,4-dideoxy-beta-D-xylo-hexopyranoside (11) showed a reduction in [H-3]GlcN and [C-14]Leu incorporation into hepatocyte cellular glycoconjugates by 89 and 88%, of the control cells, respectively, at 20 mM, whereas the free sugars, 2-acetamido-2,4-dideoxy-alpha,beta-D-xylo-hexopyranoses (15), showed a reduction of [H-3]GlcN and [C-14]Leu incorporation by 75 and 64%, respectively, at 20 mM. The acetylated analogues of 11 and 15, namely methyl 2-acetamido-3,6-di-O-acetyl-2,4-dideoxy-beta-D-xylo-hexopyranoside and 2-acetamido-1.3,6-tri-O-acetyl-2,4-dideoxy-alpha,beta-D-xylo-hexopyranoses, showed a greater inhibition of [H-3]GlcN and [C-14]Leu incorporation at 1 mM compared with their non-acetylated counterparts, but were toxic to hepatocytes at concentrations of 10 and 20 mM. Corresponding derivatives of 2-acetamido-2,4-dideoxy-L-threo-pentopyranose showed no biological effect up to 20 mM, suggesting that the C-6 substituent is important for the biological activity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00314-6

文献信息

• [EN] ANTIBODY-PYRROLOBENZODIAZEPINE DERIVATIVE CONJUGATE<br/>[FR] CONJUGUÉ ANTICORPS-DÉRIVÉ DE PYRROLOBENZODIAZÉPINE<br/>[JA] 抗体－ピロロベンゾジアゼピン誘導体コンジュゲート
  申请人：DAIICHI SANKYO CO LTD

  公开号：WO2020196474A1

  公开（公告）日：2020-10-01

  新規な抗体－ピロロベンゾジアゼンピン(PBD)誘導体コンジュゲート、当該抗体－薬物コンジュゲートを用いた腫瘍に対する治療効果を有する医薬品、及び、当該抗体－薬物コンジュゲート又は医薬品を用いた腫瘍の治療方法。
• Synthesis of 4-deoxy analogues of 2-acetamido-2-deoxy-d-glucose and 2-acetamido-2-deoxy-d-xylose and their effects on glycoconjugate biosynthesis
  作者：Ali Berkin、Mark A Szarek、Jan Plenkiewicz、Walter A Szarek*、Robert Kisilevsky*

  DOI：10.1016/s0008-6215(99)00314-6

  日期：2000.3

  4-Deoxy analogues of 2-acetamido-2-deoxy-D-glucose and 2-acetamido-2-deoxy-D-xylose were synthesized and evaluated as inhibitors of glycoconjugate biosynthesis. Methyl 2-acetamido-2,4-dideoxy-beta-D-xylo-hexopyranoside (11) showed a reduction in [H-3]GlcN and [C-14]Leu incorporation into hepatocyte cellular glycoconjugates by 89 and 88%, of the control cells, respectively, at 20 mM, whereas the free sugars, 2-acetamido-2,4-dideoxy-alpha,beta-D-xylo-hexopyranoses (15), showed a reduction of [H-3]GlcN and [C-14]Leu incorporation by 75 and 64%, respectively, at 20 mM. The acetylated analogues of 11 and 15, namely methyl 2-acetamido-3,6-di-O-acetyl-2,4-dideoxy-beta-D-xylo-hexopyranoside and 2-acetamido-1.3,6-tri-O-acetyl-2,4-dideoxy-alpha,beta-D-xylo-hexopyranoses, showed a greater inhibition of [H-3]GlcN and [C-14]Leu incorporation at 1 mM compared with their non-acetylated counterparts, but were toxic to hepatocytes at concentrations of 10 and 20 mM. Corresponding derivatives of 2-acetamido-2,4-dideoxy-L-threo-pentopyranose showed no biological effect up to 20 mM, suggesting that the C-6 substituent is important for the biological activity. (C) 2000 Elsevier Science Ltd. All rights reserved.