benzyl 2-deoxy-4-O-(diphenoxyphosphinyl)-2-<(3R)-3-tetradecanoyloxytetradecanamido>-3-O-<(3R)-3-tetradecanoyloxytetradecanoyl>-β-D-glucopyranoside | 111275-43-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2-deoxy-4-O-(diphenoxyphosphinyl)-2-<(3R)-3-tetradecanoyloxytetradecanamido>-3-O-<(3R)-3-tetradecanoyloxytetradecanoyl>-β-D-glucopyranoside
• 英文别名: benzyl 2-deoxy-4-O-phosphono-<(R)-3-tetradecanoyloxytetradecanamido>-3-O-<(R)-3-tetradecanoyloxytetradecanoyl>-β-D-glucopyranoside；benzyl 2-deoxy-4-O-diphenylphosphono-2-<(R)-3-tetradecanoyloxytetradecanamido>-3-O-<(R)-3-tetradecanoyloxytetradecanoyl>-β-D-glucopyranoside；benzyl 2-deoxy-4-O-(diphenylphosphono)-2-<(3R)-3-tetradecanoyloxytetradecanamido>-3-O-<(3R)-3-tetradecanoyloxytetradecanoyl>-β-D-glucopyranoside；[(2R,3S,4R,5R,6R)-3-diphenoxyphosphoryloxy-2-(hydroxymethyl)-6-phenylmethoxy-5-[[(3R)-3-tetradecanoyloxytetradecanoyl]amino]oxan-4-yl] (3R)-3-tetradecanoyloxytetradecanoate
• CAS: 111275-43-5
• 化学式: C₈₁H₁₃₂NO₁₄P
• 分子量: 1374.91
• InChiKey: ADEDEQMILUJOSJ-NYNGUGNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  26.5
• 重原子数：
  97
• 可旋转键数：
  65
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  191
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  benzyl 2-deoxy-4-O-(diphenoxyphosphinyl)-2-<(3R)-3-tetradecanoyloxytetradecanamido>-3-O-<(3R)-3-tetradecanoyloxytetradecanoyl>-β-D-glucopyranoside 在 钯 氢气 作用下， 以 甲醇 为溶剂， 生成
  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
• 作为产物：
  描述：

  (3R)-3-tetradecanoyloxytetradecanoic acid phenacyl ester 在 吡啶 、 4-二甲氨基吡啶 、 tetrafluoroboric acid 、 水 、 溶剂黄146 、 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 12.5h， 生成 benzyl 2-deoxy-4-O-(diphenoxyphosphinyl)-2-<(3R)-3-tetradecanoyloxytetradecanamido>-3-O-<(3R)-3-tetradecanoyloxytetradecanoyl>-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

• Lipid A and related compounds. XVII. Synthesis of 3-deoxy-D-manno-2-octulosonic acid (KDO)-(.ALPHA.2.RAR.6)-D-glucosamine-4-phosphates, analogs of the biologically active moiety of lipopolysaccharide from Escherichia coli Re mutant.
  作者：SHIN-ICHI NAKAMOTO、KAZUO ACHIWA

  DOI：10.1248/cpb.36.202

  日期：——

  Synthesis of biologically active 3-deoxy-D-manno-2-octulosonic acid (KDO)-(α2→6)-D-glucosamine-4-phosphate analogs of lipid A is described.

  描述了生物活性3-脱氧-D-manno-2-辛酮酸 (KDO)-(α2→6)-D-氨基葡萄糖-4-磷酸的脂质A类似物的合成。
• Lipid a and related compounds. Part XXV. Synthesis of the sequence of Hept-(.ALPHA.1.RAR.5)-KDO-(.ALPHA.2.RAR.6)-D-glucosamine-4-phosphate of lipopolysaccharide.
  作者：Seijiro AKAMATSU、Kiyoshi IKEDA、Kazuo ACHIWA

  DOI：10.1248/cpb.39.518

  日期：——

  We have synthesized Hept-(α1→5)-KDO-(α2→6)-D-glucosamine-4-phosphate (1), which is located in the inner core and lipid A regions of lipopolysaccharide. Compound 1 was mitogenic.

  我们合成了 Hept-(α1→5)-KDO-(α2→6)-D-氨基葡萄糖-4-磷酸（1），它位于脂多糖的内核和脂质 A 区域。化合物 1 具有有丝分裂活性。
• Conjugates of biologically active lipid a-subunit analogs with 3-deoxy-d-manno-2-octulosonic acid (KDO) and its methyl ester
  作者：Makoto Kiso、Fujita Minoru、Masanori Tanahashi、Yushun Fujishima、Yuji Ogawa、Akira Hasegawa、Frank M. Unger

  DOI：10.1016/0008-6215(88)85041-9

  日期：1988.6

  The previously described, biologically active 4- O -phosphono- d -glucosamine derivatives GLA-27, GLA-47, and GLA-60 (all related to bacterial lipid A) were converted into their respective conjugates with 3-deoxy- d - manno -2-octulosonic acid (KDO). The methyl and benzyl esters of [4,5,7,8-tetrakis- O -(chloroacetyl)-3-deoxy- d - manno -2-octulopyranosyl fluoride]onic acid and the corresponding glycosyl

  摘要将先前描述的具有生物活性的4- O-膦酰基-d-葡萄糖胺衍生物GLA-27，GLA-47和GLA-60（均与细菌脂质A有关）转化为各自的具有3-deoxy-d-的共轭物。甘露-2-氨基磺酸（KDO）。通过从甲基开始，制备了[4,5,7,8-四-O-（氯乙酰基）-3-脱氧-d-甘露聚糖-2-辛基吡喃糖基氟]酸的甲基和苄基酯和相应的糖基溴化物。 2,4,5,7,8-戊基-O-乙酰基-3-脱氧-d-甘露糖-2-辛基吡喃磺酸酯，并与膦酰基-d-葡糖胺的适当保护的前体的O-6偶联。这产生了一系列完全取代的二糖，这些二糖通过O-去（氯乙酰基）化并依次氢解去除苄基，苄氧基甲基和苯基而进行转化，
• Lipid A and Related Compounds. XXVI. Syntheses of Biologically Active Penta-O-acetyl-N-glycoloylneuraminyl- and Penta-O-acetyl-3-deoxy-D-glycero-D-galcto-2-nonulopyranosonic Acid-(.ALPHA. 2.RAR.6)-D-glucosamine-4-phosphate Analogs of Lipid A.
  作者：Kiyoshi IKEDA、Kouki KAWAI、Kazuo ACHIWA

  DOI：10.1248/cpb.39.1305

  日期：——

  The syntheses of novel penta-O-acetyl-N-glycoloylneuraminyl- and penta-O-acetyl-3-deoxy-D-glycero-D-galacto-2-nonulopyranosonic acid-(alpha 2----6)-D-glucosamine-4-phosphate analogues of lipid A containing sialic acid in place of 3-deoxy-D-manno-2-octulosonic acid are described. Preliminary examination of the biological activity revealed that two synthetic disaccharides showed mitogenic activities

  新型五-O-乙酰基-N-糖酰基神经氨酸基和五-O-乙酰基-3-脱氧-D-甘油-D-半乳糖-2-壬基吡喃磺酸-（α2 ---- 6）-D-的合成描述了含有唾液酸代替3-脱氧-D-甘露糖-2-辛磺酸的脂质A的氨基葡萄糖-4-磷酸类似物。生物学活性的初步检查表明，两种合成的二糖显示有丝分裂活性和弱的抗肿瘤活性。
• Analogs of nonreducing monosaccharide moiety of lipid A
  申请人：Toho Yakuhin Kogyo Kabushiki Kaisha

  公开号：EP0224260A2

  公开（公告）日：1987-06-03

  Provided herein is a derivative of 2-deoxy-2-amino-4-O-phophono-D-glucopyranose, which is derived from lipid A, of the formula: wherein R, and R2 are a member in a pair selected from the group consisting of those indicated in a following table; The compounds of this invention contain ones of a rectus and a sinister configurations and are expected to exhibit more improved biological and immunological activities than those which natural lipid A possesses originally.

  本发明提供了一种 2-脱氧-2-氨基-4-O-phophono-D-吡喃葡萄糖的衍生物，该衍生物来源于脂质 A，其式为 其中 R 和 R2 是选自下表所示组别的一对成员； 本发明的化合物包含直向和正向构型的化合物，与天然脂质 A 原有的生物和免疫活性相比，本发明的化合物有望表现出更好的生物和免疫活性。