benzyl 2-deoxy-2-[(R)3-hexadecanoyloxytetradecanoylamino]-3-O-(2,2,2-trichloroethoxycarbonyl)-β-D-glucopyranoside | 253119-93-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2-deoxy-2-[(R)3-hexadecanoyloxytetradecanoylamino]-3-O-(2,2,2-trichloroethoxycarbonyl)-β-D-glucopyranoside
• 英文别名: [(3R)-1-[[(2R,3R,4R,5S,6R)-5-hydroxy-6-(hydroxymethyl)-2-phenylmethoxy-4-(2,2,2-trichloroethoxycarbonyloxy)oxan-3-yl]amino]-1-oxotetradecan-3-yl] hexadecanoate
• CAS: 253119-93-6
• 化学式: C₄₆H₇₆Cl₃NO₁₀
• 分子量: 909.469
• InChiKey: QPUBJVXTGQOHLO-QZAPHFEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.1
• 重原子数：
  60
• 可旋转键数：
  37
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  150
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  benzyl 2-deoxy-2-[(R)3-hexadecanoyloxytetradecanoylamino]-3-O-(2,2,2-trichloroethoxycarbonyl)-β-D-glucopyranoside 、 2-deoxy-4-O-diphenylphosphono-3-O-[(R)-3-tetradecanoyloxytetradecanoyl]-6-O-(2,2,2-trichloro-1,1-dimethylethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl chloride 在 4 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 1,2-二氯乙烷 为溶剂， 以73%的产率得到[(3R)-1-[[(2R,3R,4R,5S,6R)-6-[[(2R,3R,4R,5S,6R)-5-diphenoxyphosphoryloxy-4-[(3R)-3-tetradecanoyloxytetradecanoyl]oxy-3-(2,2,2-trichloroethoxycarbonylamino)-6-[(1,1,1-trichloro-2-methylpropan-2-yl)oxycarbonyloxymethyl]oxan-2-yl]oxymethyl]-5-hydroxy-2-phenylmethoxy-4-(2,2,2-trichloroethoxycarbonyloxy)oxan-3-yl]amino]-1-oxotetradecan-3-yl] hexadecanoate
  参考文献：
  名称：

  Chemical Synthesis of the Major Constituents ofSalmonella MinnesotaMonophosphoryl Lipid A

  摘要：

  DOI：

  10.1080/07328309808002363
• 作为产物：
  描述：

  benzyl 2-deoxy-2-<(3R)-3-hexadecanoyloxytetradecanamido>-4,6-O-isopropylidene-β-D-glucopyranoside 在 4-二甲氨基吡啶 、 溶剂黄146 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 生成 benzyl 2-deoxy-2-[(R)3-hexadecanoyloxytetradecanoylamino]-3-O-(2,2,2-trichloroethoxycarbonyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Chemical Synthesis of the Major Constituents ofSalmonella MinnesotaMonophosphoryl Lipid A

  摘要：

  DOI：

  10.1080/07328309808002363

文献信息

• [EN] PHOSPHOGLYCOLIPID AND METHODS FOR ITS USE<br/>[FR] PHOSPHOGLYCOLIPIDE ET SES METHODES D'UTILISATION
  申请人：RIBI IMMUNOCHEM RESEARCH INC

  公开号：WO2000011010A1

  公开（公告）日：2000-03-02

  The invention concerns a novel phosphoglycolipid compound. The compound of the subject invention is 2- Deoxy-6-O- [2-deoxy-4-O -phosphono-3-O -[(R)-3- tetradecanoyloxytetradecanoyl] -2-[(R)-3- octadecanoyloxytetradecanoylamino] -β-D-glucopyranosyl] -2-[(R)-3- hexadecanoyloxytetradecanoylamino] -D-glucopyranose and pharmaceutically acceptable salts thereof. The compound is not immunoreactive, not pyrogenic, not toxic but is active in ameliorating tissue damage due to ischemia/reperfusion injury. Methods for using the subject compound to protect against reversible and irreversible damage due to ischemia/reperfusion injury are also disclosed.

  该发明涉及一种新型的磷酸甘油脂化合物。该发明的化合物是2-去氧-6-O-[2-去氧-4-O-磷酸-3-O-[(R)-3-十四酸酰氧基-十四酸酰] -2-[(R)-3-十八酸酰氧基-十四酸酰胺]-β-D-葡萄糖吡喃糖基]-2-[(R)-3-十六酸酰氧基-十四酸酰胺]-D-葡萄糖吡喃糖和其药学上可接受的盐。该化合物不具有免疫反应性、不具有致热原性、不具有毒性，但在改善因缺血/再灌注损伤引起的组织损伤方面具有活性。还公开了使用该化合物保护可逆和不可逆缺血/再灌注损伤引起的损伤的方法。
• Phosphoglycolipid and methods for its use
  申请人：——

  公开号：US20020013291A1

  公开（公告）日：2002-01-31

  The invention concerns a novel phosphoglycoilpid compound. The compound of the subject invention is 2-Deoxy-6-O-[2-deoxy-4-O-phosphono-3-O-[(R)-3-tetradecanoyloxytetradecanoyl]-2-[(R)-3-octadecanoyloxytetradecanoylamino]-&bgr;-D-glucopyranosyl]-2-[(R)-3-hexadecanoyloxytetradecanoylamino]-D-glucopyranose and pharmaceutically acceptable salts thereof. The compound is not immunoreactive, not pyrogenic, not toxic but is active in ameliorating tissue damage due to ischemia/reperfusion injury. Methods for using the subject compound to protect against reversible and irreversible damage due to ischemia/reperfusion injury are also disclosed.

  本发明涉及一种新型的磷酸甘油脂化合物。该发明的化合物是2-去氧-6-O-［2-去氧-4-O-磷酸-3-O-［(R)-3-十四烷氧基-十四烷酰基］-2-［(R)-3-十八烷氧基-十四烷酰胺］-β-D-葡萄糖苷］-2-［(R)-3-十六烷氧基-十四烷酰胺］-D-葡萄糖苷及其药学上可接受的盐。该化合物不具有免疫反应性，不具有热原性，不具有毒性，但在缓解因缺血/再灌注损伤引起的组织损伤方面具有活性。本发明还公开了使用该化合物保护免受缺血/再灌注损伤引起的可逆和不可逆损伤的方法。
• PHOSPHOGLYCOLIPID AND METHODS FOR ITS USE
  申请人：CORIXA CORPORATION

  公开号：EP1105401A1

  公开（公告）日：2001-06-13
• US6013640A
  申请人：——

  公开号：US6013640A

  公开（公告）日：2000-01-11
• Chemical Synthesis of the Major Constituents of<i>Salmonella Minnesota</i>Monophosphoryl Lipid A
  作者：David A. Johnson、C. Gregory Sowell、David S. Keegan、Mark T. Livesay

  DOI：10.1080/07328309808002363

  日期：1998.12