methyl 2-acetamido-2,4-dideoxy-β-D-xylo-hexopyranoside | 269065-39-6

• 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: methyl 2-acetamido-2,4-dideoxy-β-D-xylo-hexopyranoside
• 英文别名: Methyl 2-acetamido-2,4-dideoxy-beta-d-xylo-hexopyranoside；N-[(2R,3R,4S,6S)-4-hydroxy-6-(hydroxymethyl)-2-methoxyoxan-3-yl]acetamide
• CAS: 269065-39-6
• 化学式: C₉H₁₇NO₅
• 分子量: 219.238
• InChiKey: BKISDXCOTDQJJY-RBXMUDONSA-N

物化性质

• 沸点：
  488.9±45.0 °C(predicted)
• 密度：
  1.26±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  88
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 methyl 2-acetamido-2,4-dideoxy-β-D-xylo-hexopyranoside 在 吡啶 作用下， 反应 8.0h， 以87%的产率得到methyl 2-acetamido-3,6-di-O-acetyl-2,4-dideoxy-β-D-xylo-hexopyranoside
  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
• 作为产物：
  描述：

  甲基2-乙酰氨基-2-脱氧-3,6-二-O-苄基-beta-D-吡喃葡萄糖苷 在 palladium on activated charcoal 咪唑 、 盐酸 、 偶氮二异丁腈 、 氢气 、 三正丁基氢锡 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 反应 14.33h， 生成 methyl 2-acetamido-2,4-dideoxy-β-D-xylo-hexopyranoside
  参考文献：
  名称：

  Synthesis and biological evaluation of a radiolabeled analog of methyl 2-acetamido-2,4-dideoxy-β-d-xylo-hexopyranoside directed towards influencing cellular glycosaminoglycan biosynthesis

  摘要：

  Two methods are presented for the synthesis or methyl 2-acetamido-2,4-dideoxy-beta-D-xylo-hexopyranoside. The first method employs the Barton-McCombie deoxygenation methodology, and the second method utilizes an oxidation-beta-elimination methodology that allows for the incorporation of hydrogen isotopes into the title compound. Hence, methyl 2-acetamido-2,4-dideoxy-beta-D-xylo-hexopyranoside (4) and methyl 2-acetamido-2,4-dideoxy-beta-D-xylo-hexopyranoside-6-t (14) were synthesized and evaluated for their ability to inhibit hepatocyte, cell-surface glycosaminoglycan biosynthesis and to incorporate a [H-3] radiolabel into isolated glycosaminoglycans, respectively. Compound 4, at a concentration of 1.0 mM, demonstrated a reduction of D-[H-3]glucosamine and [S-35]sulfate incorporation into isolated glycosaminoglycans by 69 and 59%, of the control cultures, respectively. At 10 and 20 mM, 4 demonstrated a maximum inhibition of incorporation of both radiolabels to approximately 10% of the control cultures. Compound 14 demonstrated a maximum incorporation of a [H-3] radiolabel into isolated cell-surface glycosaminoglycans at 10 and 20 mM. The mechanism of inhibition of glycosaminoglycan biosynthesis is due, in part, to the incorporation of a 4-deoxy moiety into glycosaminoglycan chains resulting in premature chain termination. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00285-3

文献信息

• Synthesis and biological evaluation of a radiolabeled analog of methyl 2-acetamido-2,4-dideoxy-β-d-xylo-hexopyranoside directed towards influencing cellular glycosaminoglycan biosynthesis
  作者：Ali Berkin、Walter A Szarek、Robert Kisilevsky

  DOI：10.1016/s0008-6215(01)00285-3

  日期：2002.1

  Two methods are presented for the synthesis or methyl 2-acetamido-2,4-dideoxy-beta-D-xylo-hexopyranoside. The first method employs the Barton-McCombie deoxygenation methodology, and the second method utilizes an oxidation-beta-elimination methodology that allows for the incorporation of hydrogen isotopes into the title compound. Hence, methyl 2-acetamido-2,4-dideoxy-beta-D-xylo-hexopyranoside (4) and methyl 2-acetamido-2,4-dideoxy-beta-D-xylo-hexopyranoside-6-t (14) were synthesized and evaluated for their ability to inhibit hepatocyte, cell-surface glycosaminoglycan biosynthesis and to incorporate a [H-3] radiolabel into isolated glycosaminoglycans, respectively. Compound 4, at a concentration of 1.0 mM, demonstrated a reduction of D-[H-3]glucosamine and [S-35]sulfate incorporation into isolated glycosaminoglycans by 69 and 59%, of the control cultures, respectively. At 10 and 20 mM, 4 demonstrated a maximum inhibition of incorporation of both radiolabels to approximately 10% of the control cultures. Compound 14 demonstrated a maximum incorporation of a [H-3] radiolabel into isolated cell-surface glycosaminoglycans at 10 and 20 mM. The mechanism of inhibition of glycosaminoglycan biosynthesis is due, in part, to the incorporation of a 4-deoxy moiety into glycosaminoglycan chains resulting in premature chain termination. (C) 2002 Elsevier Science Ltd. All rights reserved.
• 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.