O-(3β)-cholest-5-en-3-yl-2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside | 1070239-82-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: O-(3β)-cholest-5-en-3-yl-2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside
• 英文别名: cholesteryl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside；cholesteryl-2,3,4,6-tetra-O-acetyl-α-D-galactopyranose
• CAS: 1070239-82-5
• 化学式: C₄₁H₆₄O₁₀
• 分子量: 716.953
• InChiKey: QAUUCWYBFGKUAM-DRRXYMJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  51.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  123.66
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  胆固醇 、 beta-D-半乳糖五乙酸酯 在 三氟化硼乙醚 、 吡啶 、 乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 6.5h， 以8%的产率得到O-(3β)-cholest-5-en-3-yl-2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside
  参考文献：
  名称：

  Facile Synthesis of a Library of Lyme Disease Glycolipid Antigens

  摘要：

  A library of one of the two Lyme disease antigens, BbGL1, has been synthesized in four steps from D-galactose using BF3-promoted glycosylation of the peracetate to introduce the cholesteryl beta-glycoside and TBTU-promoted esterification to add a range of fatty acids regioselectively at O-6 of D-galactose in good yield.

  DOI：

  10.1021/ol301697c

文献信息

• Direct Glycosylation of Bioactive Small Molecules with Glycosyl Iodide and Strained Olefin as Acid Scavenger
  作者：Xiangying Gu、Lin Chen、Xin Wang、Xiao Liu、Qidong You、Wenwei Xi、Li Gao、Guohua Chen、Yue-Lei Chen、Bing Xiong、Jingkang Shen

  DOI：10.1021/jo402551x

  日期：2014.2.7

  A new strategy for diversity-oriented direct glycosylation of bioactive small molecules was developed. This reaction features (-)-beta-pinene as acid scavenger and work with glycosyl iodides under mild conditions. With the aid of RP-HPLC and chiral SFC separation techniques, the new direct glycosylation proved effective at gram scale on bioactive small molecules including AZD6244, podophyllotoxin, paclitaxel, and docetaxel. Interesting glycoside derivatives were efficiently created with good yields and 1,2-cis selectivity.
• Two-Step Synthesis of the Immunogenic Bacterial Glycolipid BbGL1
  作者：Suvarn S. Kulkarni、Jacquelyn Gervay-Hague

  DOI：10.1021/ol801780c

  日期：2008.11.6

  Chemical synthesis of a bacterial glycolipid BbGL1 is reported in two steps starting from per-O-TMS D-galactose. The key features are glycosyl iodide mediated beta-stereoselective glycosylation in the absence of neighboring group participation and regioselective acylation.
• Novel Targeted Liposomes Deliver siRNA to Hepatocellular Carcinoma Cells<i>in vitro</i>
  作者：Shantal Dorasamy、Nicolisha Narainpersad、Moganavelli Singh、Mario Ariatti

  DOI：10.1111/j.1747-0285.2012.01446.x

  日期：2012.11

  Liposomes form a major class of non‐viral vectors for short interfering RNA delivery, however tissue and cell‐specific targeting are additional requirements in the design of short interfering RNA delivery systems with a therapeutic potential. Selective delivery of liposomes to hepatocytes may be achieved by directing complexes to the asialoglycoprotein receptor, which is expressed on hepatocytes, and which displays high affinity for the β‐d‐galactopyranosyl moiety. We aimed to show that the d‐galactopyranosyl ring in direct β‐glycosidic link to cholesterol, when formulated into liposomes with 3β[N‐(N′,N′‐dimethylaminopropane) carbamoyl] cholesterol (Chol‐T) or its quaternary trimethylammonium analogue (Chol‐Q), may promote targeted delivery of cytotoxic short interfering RNA to the human hepatoma cell line HepG2 via the asialoglycoprotein receptor. Liposome‐short interfering RNA interactions were characterized by electron microscopy, dye displacement, gel retardation and nuclease assays. Stable short interfering RNA‐protective lipoplexes were formed at N/P ratios in the range 5:1–7:1. Targeted lipoplex 4 achieved high transfection efficiencies at 50 nm short interfering RNA (70%) and <10% in a competition assay, whilst untargeted complexes reached low levels at the same concentration (<25%). Transfection efficiencies of all lipoplexes in the asialoglycoprotein receptor‐negative cell line HEK293 under the same conditions were low. Lipoplexes containing cholesteryl‐β‐d‐galactopyranoside may therefore form the basis for the development of useful hepatotropic short interfering RNA delivery vectors.