benzyl 2-deoxy-4,6-O-isopropylidene-2-<(3R)-3-tetradecanoyloxytetradecanamido>-β-D-glucopyranoside | 111247-06-4

• 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: benzyl 2-deoxy-4,6-O-isopropylidene-2-<(3R)-3-tetradecanoyloxytetradecanamido>-β-D-glucopyranoside
• 英文别名: benzyl 2-deoxy-4,6-O-isopropylidene-2-[(R)-3-tetradecanoyloxytetradecanoylamino]-β-D-glucopyranoside；benzyl 2-deoxy-4,6-O-isopropylidene-2-((3R)-3-tetradecanoyloxytetradecanamido)-β-D-glucopyranoside；[(3R)-1-[[(4aR,6R,7R,8R,8aS)-8-hydroxy-2,2-dimethyl-6-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]amino]-1-oxotetradecan-3-yl] tetradecanoate
• CAS: 111247-06-4
• 化学式: C₄₄H₇₅NO₈
• 分子量: 746.081
• InChiKey: RWMJANYNRJXVPL-HYXKATPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.2
• 重原子数：
  53
• 可旋转键数：
  30
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  benzyl 2-deoxy-4,6-O-isopropylidene-2-<(3R)-3-tetradecanoyloxytetradecanamido>-β-D-glucopyranoside 生成 benzyl 2-deoxy-4,6-O-isopropylidene-2-<(3R)-3-tetradecanoyloxytetradecanamido>-3-O-<(3R)-3-tetradecanoyloxytetradecanoyl>-β-D-glucopyranoside
  参考文献：
  名称：

  HASEGAWA, AKIRA;KISO, MAKOTO;MORIHARA, KAZUYUKI

  摘要：

  DOI：
• 作为产物：
  描述：

  (3R)-3-tetradecanoyloxytetradecanoic acid phenacyl ester 在 N,N'-二环己基碳二亚胺 、 锌 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 4.5h， 生成 benzyl 2-deoxy-4,6-O-isopropylidene-2-<(3R)-3-tetradecanoyloxytetradecanamido>-β-D-glucopyranoside
  参考文献：
  名称：

  与细菌脂质A的非还原糖亚基有关的旋光4-O-膦酰基-D-葡萄糖胺衍生物的合成。

  摘要：

  光学活性脂质A亚基的同系物，称为GLA-46，GLA-47，GLA-59和GLA-60，是通过在苄基2-氨基-2-脱氧-的N-2和O-3处连续酰化而逐步合成的。具有光学活性3-羟基十四烷酸的3-9O-（苄氧基）甲基或39O-十四烷酰基衍生物的4,6-O-异亚丙基-β-D-吡喃葡萄糖苷，并在D-葡萄糖胺残基的O-4处磷酸化。

  DOI：

  10.1016/0008-6215(87)80207-0

文献信息

• 3-<i>O</i>-Desacyl Monophosphoryl Lipid A Derivatives:  Synthesis and Immunostimulant Activities
  作者：David A. Johnson、David S. Keegan、C. Gregory Sowell、Mark T. Livesay、Craig L. Johnson、Lara M. Taubner、Annalivia Harris、Kent R. Myers、Jennifer D. Thompson、Gary L. Gustafson、Michael J. Rhodes、J. Terry Ulrich、Jon R. Ward、Yvonne M. Yorgensen、John L. Cantrell、Valerie G. Brookshire

  DOI：10.1021/jm990222b

  日期：1999.11.1

  The synthesis of a series of novel analogues of lipid A, the active principle of lipopolysaccharide, is reported. In these compounds, the 1-O-phosphono and (R)-3-hydroxytetradecanoyl moieties of native Salmonella minnesota R595 lipid A have been replaced with hydrogen and the length of the normal fatty acyl residues has been systematically varied. Normal fatty acid chain length in the 3-O-desacyl monophosphoryl lipid A (MLS) series is shown to be a critical determinant of iNOS gene expression in activated mouse macrophages and the induction of proinflammatory cytokines in human peripheral monocytes. Examination of pyrogenicity in rabbits and lethal toxicity in D-galactosamine-treated mice shows that toxic effects in the MLA series can be ameliorated by modifying fatty acid chain length. When used as an adjuvant for tetanus toroid vaccines, certain MLA derivatives enhance the production of tetanus toroid-specific antibodies in mice.
• XASEHGAVA, AKIRA;KISO, MAKOTO;MORIXARA, KADZUYUKI
  作者：XASEHGAVA, AKIRA、KISO, MAKOTO、MORIXARA, KADZUYUKI

  DOI：——

  日期：——
• HASEGAWA, AKIRA;KISO, MAKOTO;MORIHARA, KAZUYUKI
  作者：HASEGAWA, AKIRA、KISO, MAKOTO、MORIHARA, KAZUYUKI

  DOI：——

  日期：——
• US4746742A
  申请人：——

  公开号：US4746742A

  公开（公告）日：1988-05-24
• Synthesis of the optically active 4-O-phosphono-d-glucosamine derivatives related to the nonreducing-sugar subunit of bacterial lipid A
  作者：Makoto Kiso、Shinii Tanaka、Minoru Fujita、Yushun Fujishima、Yuji Ogawa、Hideharu Ishida、Akira Hasegawa

  DOI：10.1016/0008-6215(87)80207-0

  日期：1987.4

  The optically active lipid A-subunit homologs named GLA-46, GLA-47, GLA-59, and GLA-60 have been synthesized stepwise by successive acylation at N-2 and O-3 of benzyl 2-amino-2-deoxy-4,6-O-isopropylidene-beta-D-glucopyranoside with the 3-9O-(benzyloxy)methyl or 39O-tetradecanoyl derivative of optically active 3-hydroxytetradecanoic acid, and phosphorylation at O-4 of the D-glucosamine residue.

  光学活性脂质A亚基的同系物，称为GLA-46，GLA-47，GLA-59和GLA-60，是通过在苄基2-氨基-2-脱氧-的N-2和O-3处连续酰化而逐步合成的。具有光学活性3-羟基十四烷酸的3-9O-（苄氧基）甲基或39O-十四烷酰基衍生物的4,6-O-异亚丙基-β-D-吡喃葡萄糖苷，并在D-葡萄糖胺残基的O-4处磷酸化。