4,6-O-benzylidene-N-benzyloxycarbonyl-3-O-chloroacetyl-1,5-dideoxy-1,5-imino-D-glucitol | 143571-97-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,6-O-benzylidene-N-benzyloxycarbonyl-3-O-chloroacetyl-1,5-dideoxy-1,5-imino-D-glucitol
• 英文别名: benzyl (4aR,7S,8R,8aR)-8-(2-chloroacetyl)oxy-7-hydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydro-[1,3]dioxino[5,4-b]pyridine-5-carboxylate
• CAS: 143571-97-5
• 化学式: C₂₃H₂₄ClNO₇
• 分子量: 461.899
• InChiKey: GNYKGTDPORAAJM-PLHROJNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  94.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4,6-O-benzylidene-N-benzyloxycarbonyl-3-O-chloroacetyl-1,5-dideoxy-1,5-imino-D-glucitol 在 吡啶 、 4 A molecular sieve 、 DMTST 作用下， 以 苯 为溶剂， 反应 2.5h， 生成 (4aR,7S,8R,8aR)-7-Acetoxy-2-phenyl-8-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-hexahydro-[1,3]dioxino[5,4-b]pyridine-5-carboxylic acid benzyl ester
  参考文献：
  名称：

  Synthesis of 1-deoxynojirimycin-containing glycans related to the Lewis X and sialyl-Lewis X epitopes recognized by LEC-CAMs

  摘要：

  DOI：

  10.1016/s0008-6215(00)90493-2
• 作为产物：
  描述：

  4,6-O-Benzylidene-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-glucitol 、 氯乙酰氯 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到4,6-O-benzylidene-N-benzyloxycarbonyl-3-O-chloroacetyl-1,5-dideoxy-1,5-imino-D-glucitol
  参考文献：
  名称：

  Synthesis of 1-deoxynojirimycin-containing glycans related to the Lewis X and sialyl-Lewis X epitopes recognized by LEC-CAMs

  摘要：

  DOI：

  10.1016/s0008-6215(00)90493-2

文献信息

• Lewis-type sugar chain derivative
  申请人：Nippon Shinyaku Company, Limited

  公开号：US05498604A1

  公开（公告）日：1996-03-12

  The object of the present invention is to provide a new SLe-type sugar chain derivative represented by the following formula (I), which is useful as a pharmaceutical and which contains moranoline: ##STR1## wherein R.sub.1 represents hydrogen, a lower alkyl, a lower alkenyl or a lower alkynyl; R.sup.2 and R.sup.3 differ from each other and represent a galactosyl, sialylgalactosyl or fucosyl group; R.sub.4 represents a hydroxyl group or an acetamido group. The present invention comprises a sugar chain derivative containing a moranoline, and having a new structure. Possessing cell adhesion inhibitory activity, the compounds of the present invention antagonizes selectin, serving well in the treatment of inflammation, inflammation-associated thrombosis, asthma and rheumatism, and in the prevention and treatment of immunological diseases and cancer.

  本发明的目的是提供一种新的SLe型糖链衍生物，其表示为以下式子（I），该衍生物含有莫拉诺林，可用作药物：##STR1## 其中，R1代表氢、低级烷基、低级烯基或低级炔基；R2和R3不同且代表半乳糖基、唾液酸半乳糖基或岩藻糖基；R4代表羟基或乙酰胺基。本发明包括一种含有莫拉诺林的糖链衍生物，具有新的结构。该化合物具有细胞黏附抑制活性，可以拮抗选择素，适用于治疗炎症、炎症相关性血栓形成、哮喘和风湿病，以及预防和治疗免疫性疾病和癌症。
• LEWIS-TYPE SUGAR CHAIN DERIVATIVE
  申请人：NIPPON SHINYAKU COMPANY, LIMITED

  公开号：EP0627442A1

  公开（公告）日：1994-12-07

  A novel SLe-type sugar chain derivative represented by general formula [I], which is useful as a medicine and has a novel structure containing moranoline, wherein R¹ represents hydrogen, lower alkyl, lower alkenyl or lower alkynyl; R² and R³ represent each independently galactosyl, sialylgalactosyl or fucosyl; and R⁴ represents hydroxy or acetamido. This compound has the activity of inhibiting cell adhesion and inhibits secretin antagonistically, thus being useful for treating inflammation and its accompanying thrombosis, asthma and rheumatism, and for preventing and treating immunopathy and cancer.

  一种由通式[I]代表的新型SLe型糖链衍生物，该衍生物可用作药物，其结构新颖，含有吗啉，其中R¹代表氢、低级烷基、低级烯基或低级炔基；R²和R³各自独立地代表半乳糖基、半乳糖酰半乳糖基或岩藻糖基；R⁴代表羟基或乙酰氨基。该化合物具有抑制细胞粘附和拮抗抑制分泌素的活性，因此可用于治疗炎症及其伴随的血栓形成、哮喘和风湿病，以及预防和治疗免疫病和癌症。
• US5498604A
  申请人：——

  公开号：US5498604A

  公开（公告）日：1996-03-12
• Synthesis of 1-deoxynojirimycin-containing glycans related to the Lewis X and sialyl-Lewis X epitopes recognized by LEC-CAMs
  作者：Hiroyasu Furui、Makoto Kiso、Akira Hasegawa

  DOI：10.1016/s0008-6215(00)90493-2

  日期：1992.5