allyl 4,6-O-isopropylidene-α-D-glucopyranoside | 721456-18-4

• 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: allyl 4,6-O-isopropylidene-α-D-glucopyranoside
• 英文别名: (4aR,6S,7R,8R,8aS)-2,2-dimethyl-6-prop-2-enoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
• CAS: 721456-18-4
• 化学式: C₁₂H₂₀O₆
• 分子量: 260.287
• InChiKey: LMNJSNBRBQIRHF-ILAIQSSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  allyl 4,6-O-isopropylidene-α-D-glucopyranoside 在 吡啶 、 高氯酸,吡啶 作用下， 以 甲醇 、 硝基甲烷 为溶剂， 反应 3.0h， 生成 allyl 2,3-di-O-benzoyl-α-D-glucopyranoside
  参考文献：
  名称：

  线性寡糖的合成：D-葡萄糖，曲霉二糖和3-O-α-曲霉生物基-D-葡萄糖的烯丙基α-糖苷的L-甘油-α-D-甘露聚糖-戊糖基衍生物，是合成抗原的底物。

  摘要：

  Synthesis of the title oligosaccharides was performed with the use of peracetylated L-glycero-beta-D-manno-heptosyl trichloroacetimidate as the heptosyl donor and (oligo)glucosyl accepters bearing acyl and acetal protecting groups.

  DOI：

  10.1016/0008-6215(94)84242-6
• 作为产物：
  描述：

  allyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 在 sodium methylate 、 对甲苯磺酸 、 2,2-二甲氧基丙烷 作用下， 反应 5.0h， 生成 allyl 4,6-O-isopropylidene-α-D-glucopyranoside
  参考文献：
  名称：

  线性寡糖的合成：D-葡萄糖，曲霉二糖和3-O-α-曲霉生物基-D-葡萄糖的烯丙基α-糖苷的L-甘油-α-D-甘露聚糖-戊糖基衍生物，是合成抗原的底物。

  摘要：

  Synthesis of the title oligosaccharides was performed with the use of peracetylated L-glycero-beta-D-manno-heptosyl trichloroacetimidate as the heptosyl donor and (oligo)glucosyl accepters bearing acyl and acetal protecting groups.

  DOI：

  10.1016/0008-6215(94)84242-6

文献信息

• Syntheses of Glucose-Containing Lipid A Analogues and Their LPS-Antagonistic Activities
  作者：Masao Shiozaki、Hiromi Doi、Daisuke Tanaka、Takaichi Shimozato、Shin-ichi Kurakata

  DOI：10.1246/bcsj.78.1091

  日期：2005.6

  Three anomeric pairs of lipid A-type disaccharides containing a glucose on their reducing end were synthesized, and their LPS-antagonistic activities were measured. The inhibitory activities (IC50) on the LPS-induced TNFα production of these six compounds (16α, 16β, 28α, 28β, 40α, and 40β) toward human whole blood cells were 0.35, 0.42, 2.37, 1.16, 2.89, and 7.70 nM, respectively.

  合成了三对具有还原端为葡萄糖的脂质A型二糖的异构体，并测量了它们的LPS拮抗活性。这六种化合物（16α、16β、28α、28β、40α和40β）对人全血细胞中LPS诱导的TNFα产生的抑制活性（IC50）分别为0.35、0.42、2.37、1.16、2.89和7.70 nM。
• Left-Side Glucose Lipid a Analogue
  申请人：Shiozaki Masao

  公开号：US20090062214A1

  公开（公告）日：2009-03-05

  A compound having excellent macrophage activity inhibitory action, which is represented by the general following formula: wherein Q represents an oxygen atom, a C 1 -C 3 alkylene group, a —O-Alk- group or a —O-Alk-O— group (in which Alk is a C 1 -C 3 alkylene group), R 1 represents a C 1 -C 20 alkanoyl group which may be substituted, a C 3 -C 20 alkenoyl group which may be substituted or a C 3 -C 20 alkynoyl group which may be substituted, R 2 , R 3 and R 4 , which may be the same or different, represent a hydrogen atom, a C 1 -C 20 alkyl group which may be substituted, a C 2 -C 20 alkenyl group which may be substituted, a C 2 -C 20 alkynyl group which may be substituted, a C 1 -C 20 alkanoyl group which may be substituted, a C 3 -C 20 alkenoyl group which may be substituted or a C 3 -C 20 alkynoyl group which may be substituted, R 5 represents a hydrogen atom, a halogen atom, a hydroxyl group, a C 1 -C 6 alkoxy group which may be substituted, a C 2 -C 6 alkenyloxy group which may be substituted or a C 2 -C 6 alkynyloxy group which may be substituted, and W represents an oxygen atom or a —NH— group, or a pharmacologically acceptable salt thereof.

  一种具有出色的巨噬细胞活性抑制作用的化合物，其通式如下：其中，Q代表氧原子、C1-C3烷基、—O-Alk-基团或—O-Alk-O—基团（其中，Alk代表C1-C3烷基），R1代表C1-C20烷酰基，可以被取代的C3-C20烯酰基或可以被取代的C3-C20炔酰基，R2、R3和R4，可以相同也可以不同，代表氢原子、可以被取代的C1-C20烷基、可以被取代的C2-C20烯基、可以被取代的C2-C20炔基、可以被取代的C1-C20烷酰基、可以被取代的C3-C20烯酰基或可以被取代的C3-C20炔酰基，R5代表氢原子、卤原子、羟基、可以被取代的C1-C6烷氧基、可以被取代的C2-C6烯氧基或可以被取代的C2-C6炔氧基，W代表氧原子或—NH—基团，或其药学上可接受的盐。
• LEVULOSE GLUCOSELIPID A ANALOGUE
  申请人：Sankyo Company, Limited

  公开号：EP1702926A1

  公开（公告）日：2006-09-20

  A compound having excellent macrophage activity inhibitory action, which is represented by the general following formula: [wherein Q represents an oxygen atom, a C1-C3 alkylene group, a -O-Alk- group or a -O-Alk-O- group (in which Alk is a C1-C3 alkylene group), R1 represents a C1-C20 alkanoyl group which may be substituted, a C3-C20 alkenoyl group which may be substituted or a C3-C20 alkynoyl group which may be substituted, R2, R3 and R4, which may be the same or different, represent a hydrogen atom, a C1-C20 alkyl group which may be substituted, a C2-C20 alkenyl group which may be substituted, a C2-C20 alkynyl group which may be substituted, a C1-C20 alkanoyl group which may be substituted, a C3-C20 alkenoyl group which may be substituted or a C3-C20 alkynoyl group which may be substituted, R5 represents a hydrogen atom, a halogen atom, a hydroxyl group, a C1-C6 alkoxy group which may be substituted, a C2-C6 alkenyloxy group which may be substituted or a C2-C6 alkynyloxy group which may be substituted, and W represents an oxygen atom or a -NH- group], or a pharmacologically acceptable salt thereof.

  一种具有优异的巨噬细胞活性抑制作用的化合物，其通式如下： [其中 Q 代表氧原子、C1-C3 亚烷基、-O-Alk- 基团或 -O-Alk-O- 基团（其中 Alk 为 C1-C3 亚烷基）、 R1 代表可被取代的 C1-C20 烷酰基、可被取代的 C3-C20 烯酰基或可被取代的 C3-C20 炔酰基、 R2、R3 和 R4（可以相同或不同）代表氢原子、可被取代的 C1-C20 烷基、可被取代的 C2-C20 烯基、可被取代的 C2-C20 烷炔基、可被取代的 C1-C20 烷酰基、可被取代的 C3-C20 烯酰基或可被取代的 C3-C20 烷炔基、 R5 代表氢原子、卤素原子、羟基、可被取代的 C1-C6 烷氧基、可被取代的 C2-C6 烯氧基或可被取代的 C2-C6 烷炔氧基，以及 W 代表氧原子或-NH-基团]，或其药理学上可接受的盐。
• EP1702926
  申请人：——

  公开号：——

  公开（公告）日：——