Allyl 2-deoxy-4,6-O-isopropylidene-2-triflouroacetamido-β-D-glucopyranoside | 135226-04-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: Allyl 2-deoxy-4,6-O-isopropylidene-2-triflouroacetamido-β-D-glucopyranoside
• 英文别名: allyl 2-deoxy-4,6-O-isopropylidene-2-trifluoroacetylamino-β-D-glucopyranoside；allyl 2-deoxy-4,6-O-isopropylidene-2-trifluoroacetamido-β-D-glucopyranoside；allyl 2-deoxy-4,6-O-isopropylidene-2-trifluoroacetamide-β-D-glucopyranoside；N-[(4aR,6R,7R,8R,8aS)-8-hydroxy-2,2-dimethyl-6-prop-2-enoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]-2,2,2-trifluoroacetamide
• CAS: 135226-04-9
• 化学式: C₁₄H₂₀F₃NO₆
• 分子量: 355.311
• InChiKey: IBHZTQBRCYUFOV-ISUQUUIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Allyl 2-deoxy-4,6-O-isopropylidene-2-triflouroacetamido-β-D-glucopyranoside 在 氢氧化钾 、 WSC*HCl 、 sodium hydride 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 生成 allyl 3-O-decyl-2-deoxy-4,6-O-isopropylidene-2-(3-oxotetardecanoylamino)-β-D-glucopyranoside
  参考文献：
  名称：

  Syntheses of glucose-containing E5564 analogues and their LPS-antagonistic activities

  摘要：

  Lipid A analogues containing a glucose moiety on their non-reducing end were synthesized, and their LPS-antagonistic activities were measured. The inhibitory activities (IC50) on LPS-induced TNF alpha production of these six compounds, 26, 33, 440, 520, 59, and 61, toward human whole blood cells were 0.49, 0.65, 0.51, 0.98, 0.46, and 1.11 nM, respectively. Inhibitory doses (ID50) of compounds 26, 33, 440, 59, and 61 on TNF alpha production induced by coinjection of galactosamine and LPS in C3HMeN mice were measured. The ID50 values of these compounds were 0.45, 0.96, < 0.2, 1.08, and < 0.2 mg/kg, respectively. Moreover, C3H/HeN mice preinjected with compounds 26, 33, and 440 were protected from lethality induced by coinjection of galactosamine and LPS. Out of eight mice preinjected with 1 mg/kg of compounds 26, 33, and 440, five, eight and six mice were protected, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.115
• 作为产物：
  描述：

  allyl 2-deoxy-2-trifluoroacetylamino-D-glucopyranoside 、 2,2-二甲氧基丙烷 在 4-甲基苯磺酸吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以28.7%的产率得到2-丙烯-1-基 2-脱氧-4,6-O-(1-甲基乙亚基)-2-[(2,2,2-三氟乙酰基)氨基]-alpha-D-吡喃葡萄糖苷
  参考文献：
  名称：

  2-脱氧-2-[（（3R）-3-羟基十四烷酰胺基] -3-O-[（3R）-3-羟基四癸基]-α-D-吡喃葡萄糖基磷酸二氢盐和2-脱氧-2-[（3R）的合成-3-羟基十四烷酰胺基] -3-O-[（3R）-3-羟基十四烷基] -4-O-膦酰基-D-吡喃葡萄糖。

  摘要：

  Both a 3-O-alkyl lipid X analogue and its 4-O-phosphono isomer were synthesized from allyl 2-deoxy-4,6-O-isopropylidene-2-trifluoroacetamido-alpha-D-glucopyranoside.

  DOI：

  10.1016/0008-6215(91)89006-2

文献信息

• Synthesis of 2-deoxy-2-[(2,2-difluoro-3-hydroxytetradecanoyl)amino]-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-D-glucopyranose 4-phosphate
  作者：Masao Shiozaki、Yoshiyuki Kobayashi、Masami Arai、Takashi Watanabe、Tetsuo Hiraoka、Masahiro Nishijima、Sayuri Kuge、Toshiaki Otsuka、Yuzuru Akamatsu

  DOI：10.1021/jm00112a045

  日期：1991.8

  radecanoyl]-D-glucopyranose 4-phosphates (9H,L) were synthesized from allyl 2-amino-2-deoxy-4,6-O- isopropylidene-beta-D-glucopyranoside (1), (+/-)-3-[(benzyloxycarbonyl)oxy]-2,2-difluorotetradecanoic acid, and (R)-3- (tetradecanoyloxy)tetradecanoic acid. Both compounds 9H and 9L were more active than GLA-60 for the prostaglandin D2 releasing test on macrophages.

  将2-脱氧-2-[（（2,2-二氟-3-羟基十四烷酰基）氨基] -3-O-[（R）-3-（十四烷酰氧基）十四烷酰基] -D-吡喃葡萄糖4-磷酸盐（9H，L）由烯丙基2-氨基-2-脱氧-4,6-O-异亚丙基-β-D-吡喃葡萄糖苷（1），（+/-）-3-[（苄氧羰基）氧基] -2,2-二氟十四烷酸合成，和（R）-3-（十四烷酰氧基）十四烷酸。化合物9H和9L对巨噬细胞上的前列腺素D2释放测试均比GLA-60更具活性。
• Synthesis of lipid A analogues containing glucose instead of glucosamine and their LPS-antagonistic activities
  作者：Masao Shiozaki、Yukiko Watanabe、Yuji Iwano、Toshio Kaneko、Hiromi Doi、Daisuke Tanaka、Takaichi Shimozato、Shin-ichi Kurakata

  DOI：10.1016/j.tet.2005.03.034

  日期：2005.5

  Lipid A analogues containing glucose in substitution for glucosamine on the reducing end were synthesized, and the inhibitory activities on LPS-induced TNF alpha production (LPS-antagonistic activity) in vitro using human whole blood cells were measured. The IC50 values (nM) of these ten compounds, 8, 14, 21, 31, 40, 51, 57, 62, 67 and 72, were 11.2, 15.4, 2.7, 0.1, 0.4, 1.3, 3.2, 3.2, 1.4 and 14.4, respectively. And also inhibitory activities (ID50) on TNF alpha production toward galactosamine loaded C3H/HeN mice in vivo of compounds 21, 31, 57, 62 and 67 were measured. The values of these compounds were 0.29, 0.50, 0.61, not dose-dependent and 0.33 mg/kg, respectively. (c) 2005 Elsevier Ltd. All rights reserved.
• EP1702926
  申请人：——

  公开号：——

  公开（公告）日：——