4,6-O-Benzylidene-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-glucitol

• 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-1,5-dideoxy-1,5-imino-D-glucitol
• 英文别名: N-Carbobenzyloxy-4,6-O-benzylidene-1-deoxynojirimycin；benzyl (4aR,7S,8R,8aR)-7,8-dihydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydro-[1,3]dioxino[5,4-b]pyridine-5-carboxylate
• 化学式: C₂₁H₂₃NO₆
• 分子量: 385.417
• InChiKey: GBRJHLWAZWZRJM-XBYSNUDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  88.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,6-O-Benzylidene-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-glucitol 在 吡啶 、 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 2-O-acetyl-4,6-O-benzylidene-N-benzyloxycarbonyl-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
• 作为产物：
  描述：

  1-脱氧野尻霉素 在 4 A molecular sieve 、 碳酸氢钠 、 zinc(II) chloride 作用下， 生成 4,6-O-Benzylidene-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-glucitol
  参考文献：
  名称：

  Selective functionalization of the C2 hydroxyl group of N-carbobenzyloxy-4,6--benzylidene-1-deoxynojirimycin

  摘要：

  1-Deoxynojirimycin was converted into its N-CBZ-4,6-O-benzylidene derivative 2 in two steps in 51% yield. Compound 2 could be regioselectively functionalized at the C2 hydroxyl group by activation with di-n-butyltin oxide, followed by reaction of the resulting stannylene with electrophiles. In this manner, the 2-O-benzoyl and 2-O-tosyl analogs could be obtained in yields of 73% and 94%, respectively.

  DOI：

  10.1016/s0040-4039(00)93531-7

文献信息

• MORANOLINE DERIVATIVE
  申请人：NIPPON SHINYAKU COMPANY, LIMITED

  公开号：EP0655457A1

  公开（公告）日：1995-05-31

  A novel sialic acid derivative containing moranoline, represented by general formula (I), which has a cell fusion inhibitor activity and is useful as a medicine for preventing or treating inflammation and accompanying thrombosis, rheumatism, immuno-logical diseases, viral infections and cancer, wherein R¹ represents hydrogen or lower alkyl and R² represents hydroxy or lower alkoxy, or alternatively R¹ and R² may be combined together to represent a single bond; and R³s may be the same or different from one another and each represents hydrogen or acetyl.

  一种新型的唾液酸衍生物，包含莫拉诺林，其通式表示为(I)，具有细胞融合抑制剂活性，可用作预防或治疗炎症和伴随的血栓形成、风湿病、免疫疾病、病毒感染和癌症的药物。其中，R¹代表氢或低碳基，R²代表羟基或低烷氧基，或者R¹和R²可以结合在一起表示单键；R³可以相同或不同，每个代表氢或乙酰基。
• 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。
• Novel diacylated and mono-acylated alkylated imino sugars exhibiting glucosidase inhibition and their method of use
  申请人：Baruch S. Blumberg Institute

  公开号：US20170305856A1

  公开（公告）日：2017-10-26

  Described herein are alkylated imino sugars derivatives having a disease-modifying action in the treatment of diseases associated with glucosidase activity that include viral hemorrhagic fevers and other enveloped viruses, and any other diseases involving glucosidase activity.
• US5498604A
  申请人：——

  公开号：US5498604A

  公开（公告）日：1996-03-12
• Selective functionalization of the C2 hydroxyl group of N-carbobenzyloxy-4,6--benzylidene-1-deoxynojirimycin
  作者：Daniel P. Getman、Gary A. DeCrescenzo、Robert M. Heintz

  DOI：10.1016/s0040-4039(00)93531-7

  日期：1991.10

  1-Deoxynojirimycin was converted into its N-CBZ-4,6-O-benzylidene derivative 2 in two steps in 51% yield. Compound 2 could be regioselectively functionalized at the C2 hydroxyl group by activation with di-n-butyltin oxide, followed by reaction of the resulting stannylene with electrophiles. In this manner, the 2-O-benzoyl and 2-O-tosyl analogs could be obtained in yields of 73% and 94%, respectively.