1,3-di-O-benzyl-2-O-(2,3,4-tri-O-benzyl-β-D-galactopyranosyl)-glycerol | 444808-94-0

• 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-(2,3,4-tri-O-benzyl-β-D-galactopyranosyl)-glycerol
• 英文别名: [(2R,3S,4S,5R,6R)-6-[1,3-bis(phenylmethoxy)propan-2-yloxy]-3,4,5-tris(phenylmethoxy)oxan-2-yl]methanol
• CAS: 444808-94-0
• 化学式: C₄₄H₄₈O₈
• 分子量: 704.86
• InChiKey: CMJQQIQXBZMUTN-NXSMLEGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  52
• 可旋转键数：
  20
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  84.8
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,3-di-O-benzyl-2-O-(2,3,4-tri-O-benzyl-β-D-galactopyranosyl)-glycerol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以0.90 g的产率得到(2S,3R,4S,5R,6R)-6-[1,3-bis(phenylmethoxy)propan-2-yloxy]-3,4,5-tris(phenylmethoxy)oxane-2-carbaldehyde
  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-di-O-benzyl-2-O-(2,3,4-tri-O-benzyl-6-O-trityl-β-D-galactopyranosyl)glycerol 在 盐酸 作用下， 以 水 、 丙酮 为溶剂， 反应 0.75h， 以92%的产率得到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

文献信息

• 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