1,3-di-O-benzyl-2-O-β-D-(galactopyranosyl)-glycerol | 444808-91-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 1,3-di-O-benzyl-2-O-β-D-(galactopyranosyl)-glycerol
• 英文别名: (2R,3R,4S,5R,6R)-2-[1,3-bis(phenylmethoxy)propan-2-yloxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 444808-91-7
• 化学式: C₂₃H₃₀O₈
• 分子量: 434.486
• InChiKey: YMYRXOZFKYAJTQ-BMXMUORJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  118
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,3-di-O-benzyl-2-O-β-D-(galactopyranosyl)-glycerol 在 吡啶 、 盐酸 、 sodium hydride 作用下， 以 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 5.25h， 生成 1,3-di-O-benzyl-2-O-(2,3,4-tri-O-benzyl-β-D-galactopyranosyl)-glycerol
  参考文献：
  名称：

  Synthesis of Isosteric Analogues of Acylglycosylglycerols Active as Chemoprevention Agents

  摘要：

  DOI：

  10.1002/1099-0690(200204)2002:8<1429::aid-ejoc1429>3.0.co;2-2
• 作为产物：
  描述：

  1,3-双(苄氧基)-2-丙醇 、 beta-D-半乳糖五乙酸酯 在 三氟化硼乙醚 、 sodium methylate 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 2.0h， 以90%的产率得到1,3-di-O-benzyl-2-O-β-D-(galactopyranosyl)-glycerol
  参考文献：
  名称：

  Synthesis of Isosteric Analogues of Acylglycosylglycerols Active as Chemoprevention Agents

  摘要：

  DOI：

  10.1002/1099-0690(200204)2002:8<1429::aid-ejoc1429>3.0.co;2-2

文献信息

• Anti-tumor-promoting activity of simple models of galactoglycerolipids with branched and unsaturated acyl chains
  作者：Diego Colombo、Laura Franchini、Lucio Toma、Fiamma Ronchetti、Nami Nakabe、Takako Konoshima、Hoyoku Nishino、Harukuni Tokuda

  DOI：10.1016/j.ejmech.2004.09.021

  日期：2005.1

  l skeleton, were tested for their anti-tumor-promoting activity using a short-term in vitro assay for Epstein-Barr virus early antigen (EBV-EA) activation. All these compounds were more active than their linear or saturated reference compounds in inhibiting the EBV activation promoted by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA), the diester 1-O-(4-methylpentanoyl)-2-O-[6-O-(4-

  测试了六个新的半乳糖甘油类似物，其中一个或两个4-甲基戊酰基或反-2-丁烯酰基与2-O-β-D-半乳糖基甘油骨架相连，并通过短期测试了它们的抗肿瘤活性EB病毒早期抗原（EBV-EA）激活的体外测定。所有这些化合物在抑制肿瘤启动子12-O-十四烷酰phorbol-13-乙酸酯（TPA），二酯1-O-（4-甲基戊酰）-2-促进的EBV活化方面均比其线性或饱和参照化合物更有活性。直到现在测试的O- [6-O-（4-甲基戊酰基）-β-D-吡喃半乳糖基] -sn-甘油产生最活跃的糖脂类类似物。在体内两阶段致癌性试验中测试时，四种化合物（三种丁烯酸酯和一种4-甲基戊酸酯）还表现出对小鼠皮肤肿瘤促进作用的抑制作用。
• Cyclic and branched acyl chain galactoglycerolipids and their effect on anti-tumor-promoting activity
  作者：Diego Colombo、Laura Franchini、Lucio Toma、Fiamma Ronchetti、Reiko Tanaka、Junko Takayasu、Hoyoku Nishino、Harukuni Tokuda

  DOI：10.1016/j.ejmech.2006.07.007

  日期：2006.12

  Fifteen new galactoglycerolipid analogues, in which one or two branched, alicyclic or aromatic acyl chains are linked to 2-O-beta-D-galacto-sylglycerol (6'-position or 1,6' positions), were prepared and tested for their anti-tumor-promoting activity using a short-term in vitro assay for Epstein-Barr virus early antigen (EBV-EA) activation. All compounds were active in inhibiting the EBV activation promoted by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA), the branched compounds resulting in the most active glycoglycerolipid analogues of the series. The branched 2-O-[6-O-(3-methylbutanoyl)-beta-D-galactopyranosyll-sn-glyceroI (1a) and the structurally related alicyclic 2-O-[6-O-(2-cyclohexylethanoyl)-beta-D-galactopyranosyl]-sn-glycerol (1d), when tested in an in vivo two-stage carcinogenesis test, exhibited inhibitory effects on mouse skin tumor promotion. (c) 2006 Elsevier Masson SAS. All rights reserved.
• Synthesis of Isosteric Analogues of Acylglycosylglycerols Active as Chemoprevention Agents
  作者：Federica Compostella、Diego Colombo、Patrizia Ferraboschi、Antonio Scala、Lucio Toma、Fiamma Ronchetti

  DOI：10.1002/1099-0690(200204)2002:8<1429::aid-ejoc1429>3.0.co;2-2

  日期：2002.4