(diphenylmethoxycarbonyl)methyl 2-[(R)-3-(benzyloxy)tetradecanamido]-3-O-[(R)-3-(benzyloxy)tetradecyl]-2-deoxy-α-D-glucopyranoside | 366805-12-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (diphenylmethoxycarbonyl)methyl 2-[(R)-3-(benzyloxy)tetradecanamido]-3-O-[(R)-3-(benzyloxy)tetradecyl]-2-deoxy-α-D-glucopyranoside
• 英文别名: benzhydryl 2-[(2S,3R,4R,5S,6R)-5-hydroxy-6-(hydroxymethyl)-3-[[(3R)-3-phenylmethoxytetradecanoyl]amino]-4-[(3R)-3-phenylmethoxytetradecoxy]oxan-2-yl]oxyacetate
• CAS: 366805-12-1
• 化学式: C₆₃H₉₁NO₁₀
• 分子量: 1022.42
• InChiKey: XCLMLAWBPVVRIE-ABHJBUTISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.9
• 重原子数：
  74
• 可旋转键数：
  41
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  142
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (diphenylmethoxycarbonyl)methyl 2-[(R)-3-(benzyloxy)tetradecanamido]-3-O-[(R)-3-(benzyloxy)tetradecyl]-2-deoxy-α-D-glucopyranoside 、 2,2,2-Trichloro-acetimidic acid (3R,4R,5S,6R)-6-benzyloxycarbonyloxymethyl-5-(diphenoxy-phosphoryloxy)-4-((R)-3-dodecyloxy-tetradecyloxy)-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yl ester 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以471 mg的产率得到benzhydryl 2-[(2S,3R,4R,5S,6R)-6-[[(2R,3R,4R,5S,6R)-5-diphenoxyphosphoryloxy-4-[(3R)-3-dodecoxytetradecoxy]-6-(phenylmethoxycarbonyloxymethyl)-3-(2,2,2-trichloroethoxycarbonylamino)oxan-2-yl]oxymethyl]-5-hydroxy-3-[[(3R)-3-phenylmethoxytetradecanoyl]amino]-4-[(3R)-3-phenylmethoxytetradecoxy]oxan-2-yl]oxyacetate
  参考文献：
  名称：

  Synthesis of lipid A type carboxymethyl derivatives with ether chains instead of ester chains and their LPS-antagonistic activities

  摘要：

  Synthesis of lipid A type carboxymethyl derivatives having ether chains at both the C-3 and C-3' positions and their LPS-antagonistic activities toward human U937 cells are described. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00357-9
• 作为产物：
  描述：

  Allyl 3-O-<(3R)-3-benzyloxytetradecanyl>-2-deoxy-4,6-O-isopropylidene-2-trifluoroacetamido-α-D-glucopyranoside 在 lead(IV) acetate 、 sodium hydroxide 、 sodium chlorite 、 sodium dihydrogenphosphate 、 四氧化锇 、 2-甲基-2-丁烯 、 溶剂黄146 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 乙醇 、 水 、 乙酸乙酯 、 叔丁醇 、 苯 为溶剂， 反应 67.0h， 生成 (diphenylmethoxycarbonyl)methyl 2-[(R)-3-(benzyloxy)tetradecanamido]-3-O-[(R)-3-(benzyloxy)tetradecyl]-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of lipid A type carboxymethyl derivatives with ether chains instead of ester chains and their LPS-antagonistic activities

  摘要：

  Synthesis of lipid A type carboxymethyl derivatives having ether chains at both the C-3 and C-3' positions and their LPS-antagonistic activities toward human U937 cells are described. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00357-9

文献信息

• Synthesis of lipid A type carboxymethyl derivatives with ether chains instead of ester chains and their LPS-antagonistic activities
  作者：Yukiko Watanabe、Kumiko Miura、Masao Shiozaki、Saori Kanai、Shin-ichi Kurakata、Masahiro Nishijima

  DOI：10.1016/s0008-6215(02)00357-9

  日期：2003.1

  Synthesis of lipid A type carboxymethyl derivatives having ether chains at both the C-3 and C-3' positions and their LPS-antagonistic activities toward human U937 cells are described. (C) 2002 Elsevier Science Ltd. All rights reserved.