allyl 6-O-(tert-butyldimethylsilyl)-3-O-decyl-2-deoxy-2-(3-oxotetradecanoylamino)-β-D-glucopyranoside | 859508-27-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 6-O-(tert-butyldimethylsilyl)-3-O-decyl-2-deoxy-2-(3-oxotetradecanoylamino)-β-D-glucopyranoside
• 英文别名: allyl 6-O-(t-butyldimethylsilyl)-3-O-decyl-2-deoxy-2-(3-oxotetradecanoylamino)-β-D-glucopyranoside；N-[(2R,3R,4R,5S,6R)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-decoxy-5-hydroxy-2-prop-2-enoxyoxan-3-yl]-3-oxotetradecanamide
• CAS: 859508-27-3
• 化学式: C₃₉H₇₅NO₇Si
• 分子量: 698.113
• InChiKey: SAQGRQORUVIVJW-GEOORHAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.19
• 重原子数：
  48
• 可旋转键数：
  30
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  allyl 6-O-(tert-butyldimethylsilyl)-3-O-decyl-2-deoxy-2-(3-oxotetradecanoylamino)-β-D-glucopyranoside 在 (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate 吡啶 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 氢氟酸 、 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 30.17h， 生成 4-O-(allyloxycarbonyl)-3-O-decyl-2-deoxy-6-O-{4-O-(diallylphosphono)-3-O-[(R)-3-methoxydecyl]-6-O-methyl-2-O-[(Z)-11-octadecenoyl]-β-D-glucopyranosyl}-2-(3-oxotetradecanoylamino)-α-D-glucopyranose
  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：

  methanesulfonic acid decyl ester 在 4-二甲氨基吡啶 、 氢氧化钾 、 WSC*HCl 、 sodium hydride 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.5h， 生成 allyl 6-O-(tert-butyldimethylsilyl)-3-O-decyl-2-deoxy-2-(3-oxotetradecanoylamino)-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

文献信息

• EP1702926
  申请人：——

  公开号：——

  公开（公告）日：——
• Syntheses of glucose-containing E5564 analogues and their LPS-antagonistic activities
  作者：Masao Shiozaki、Hiromi Doi、Daisuke Tanaka、Takaichi Shimozato、Shin-ichi Kurakata

  DOI：10.1016/j.tet.2005.09.115

  日期：2006.1

  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.