undecyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside | 433930-29-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: undecyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside
• 英文别名: n-undecanyl 2,3,4,6-tetra-O-α-D-galactopyranoside
• CAS: 433930-29-1
• 化学式: C₂₅H₄₂O₁₀
• 分子量: 502.602
• InChiKey: ABQQGUWIDBLJRM-MQZWXTIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  35.0
• 可旋转键数：
  16.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  123.66
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  undecyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以100%的产率得到undecyl α-D-galactopyranoside
  参考文献：
  名称：

  The anomeric mixture of some O-galactolipid derivatives is more toxic against cancer cells than either anomer alone

  摘要：

  The anomeric mixture of a series of O-galactolipid derivatives is revealed to be more toxic against several cancer cell lines than their either single component with the pure alpha- or beta-configuration. This interesting phenomenon has been confirmed on pairs of synthesized O-galactosyl anomers bearing length-varied alkyl chains at the lipid end. Furthermore, the most potent mixture was determined inoffensive to a normal cell line tested. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.069
• 作为产物：
  描述：

  十一烷醇 、 2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 在 三氟化硼乙醚 作用下， 以 乙腈 为溶剂， 反应 0.2h， 以19.1%的产率得到undecyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside
  参考文献：
  名称：

  The anomeric mixture of some O-galactolipid derivatives is more toxic against cancer cells than either anomer alone

  摘要：

  The anomeric mixture of a series of O-galactolipid derivatives is revealed to be more toxic against several cancer cell lines than their either single component with the pure alpha- or beta-configuration. This interesting phenomenon has been confirmed on pairs of synthesized O-galactosyl anomers bearing length-varied alkyl chains at the lipid end. Furthermore, the most potent mixture was determined inoffensive to a normal cell line tested. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.069

文献信息

• Konstantinović; Dimitrijević; Radulović, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 3, p. 598 - 603
  作者：Konstantinović、Dimitrijević、Radulović

  DOI：——

  日期：——
• Synthesis and properties of new bolaform and macrocyclic galactose-based surfactants obtained by olefin metathesis
  作者：Céline Satgé、Robert Granet、Bernard Verneuil、Yves Champavier、Pierre Krausz

  DOI：10.1016/j.carres.2004.03.003

  日期：2004.5

  A series of galactose-based surfactants with various structures likely to display new interesting properties were synthesized. Four monocatenary surfactants were elaborated by microwave-assisted galactosylation of undecanol or 10-undecenol. These compounds were slightly soluble in water. Their tensioactive properties were determined at 45 degreesC. Olefin metathesis was used to synthesize the two single-chain bolaforms from undec-10-enyl galactopyranosides; two pseudomacrocyclic bolaforms were prepared by grafting two carbamates at O-4 and O-4' sugar positions of the single-chain bolaforms. These four surfactants are insoluble in water and undergo monolayer compression. Cyclization of these bolaforms by olefin metathesis led to macrocyclic surfactant analogues of archaeobacterial membrane components. (C) 2004 Published by Elsevier Ltd.