methyl 2-acetamido-2-deoxy-6-O-triphenylmethyl-β-D-glucopyranoside | 69892-34-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: methyl 2-acetamido-2-deoxy-6-O-triphenylmethyl-β-D-glucopyranoside
• 英文别名: Methyl-2-acetamido-6-O-trityl-2-deoxy-β-D-glucopyranosid；N-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-2-methoxy-6-(trityloxymethyl)oxan-3-yl]acetamide
• CAS: 69892-34-8
• 化学式: C₂₈H₃₁NO₆
• 分子量: 477.557
• InChiKey: PBGYXSBHLGTVLP-RFNQJFSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  97.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-acetamido-2-deoxy-6-O-triphenylmethyl-β-D-glucopyranoside 在 palladium on activated charcoal sodium tetrahydroborate 、 甲酸 、 sodium borotritide 、 pyridine-SO3 complex 、 氢气 、 三乙胺 作用下， 以 吡啶 、 甲醇 、 乙醚 、 二甲基亚砜 为溶剂， 反应 101.58h， 生成 N-[(2R,3R,4S,6S)-4-hydroxy-6-[hydroxy(tritio)methyl]-2-methoxyoxan-3-yl]acetamide
  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：

  三苯基氯甲烷 、 甲基2-乙酰氨基-2-脱氧-BETA-D-吡喃葡萄糖苷 以 吡啶 为溶剂， 反应 96.0h， 以79.1%的产率得到methyl 2-acetamido-2-deoxy-6-O-triphenylmethyl-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.