methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-[(methylthio)thiocarbonyl]-β-D-glucopyranoside | 412926-33-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-[(methylthio)thiocarbonyl]-β-D-glucopyranoside
• 英文别名: O-[(2R,3S,4R,5R,6R)-5-acetamido-6-methoxy-4-phenylmethoxy-2-(phenylmethoxymethyl)oxan-3-yl] methylsulfanylmethanethioate
• CAS: 412926-33-1
• 化学式: C₂₅H₃₁NO₆S₂
• 分子量: 505.656
• InChiKey: AGZVJDMDJROADU-MRKXFKPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  133
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-[(methylthio)thiocarbonyl]-β-D-glucopyranoside 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 0.33h， 以70%的产率得到methyl 2-acetamido-3,6-di-O-benzyl-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
• 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 咪唑 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 methyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-[(methylthio)thiocarbonyl]-β-D-glucopyranoside
  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.