cholesteryl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside

• 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: cholesteryl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside
• 英文别名: [(2R,3S,6R)-3-acetyloxy-6-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• 化学式: C₃₇H₅₈O₆
• 分子量: 598.864
• InChiKey: QJXHEXDGVGHSCW-YZWAMXLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  胆固醇 、 乙酰化葡萄烯糖 在 硫酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以85%的产率得到cholesteryl 4,6-di-O-acetyl-2,3-dideoxy-β-D-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  A Facile H2SO4/4 Å Molecular Sieves Catalyzed Synthesis of 2,3-Unsaturated O-Glycosides via Ferrier-Type Rearrangement

  摘要：

  开发了一种无金属催化体系的新方法来合成2,3-不饱和糖苷。这种催化剂，即硫酸/4 Å分子筛，可以在室温下催化3,4,6-三-O-乙酰基-d-葡醛酸与多种醇的反应，通过Ferrier型重排得到高α-选择性（α/β > 6:1）的2,3-不饱和糖苷。

  DOI：

  10.1055/s-0029-1219539

文献信息

• Ceric(iv) ammonium nitrate-catalyzed glycosidation of glycals: a facile synthesis of 2,3-unsaturated glycosides
  作者：Jhillu S. Yadav、Basi V. Subba Reddy、Sushil Kumar Pandey

  DOI：10.1039/b009973m

  日期：——

  Glycosidation of glycals with alcohols in the presence of a catalytic amount of ceric(IV) ammonium nitrate under neutral conditions proceeds smoothly in refluxing acetonitrile to afford the corresponding 2,3-unsaturated glycosides in excellent yields.

  在温和条件下，以催化量的硝酸铈铵作为催化剂，糖酸内酯与醇在回流的乙腈中进行甘露糖基化反应，能够高效地生成相应的2,3-不饱和糖苷。
• Nitrosyl Tetrafluoroborate Catalyzed Preparation of 2,3-Unsaturated Glycosides and 2-Deoxyglycosides of Hindered Alcohols, Thiols, and Sulfonamides
  作者：Anup Misra、Abhishek Santra、Goutam Guchhait

  DOI：10.1055/s-0032-1318406

  日期：——

  Nitrosyl tetrafluoroborate (NOBF4) has been successfully applied as an efficient organocatalyst for the preparation of 2,3-unsaturated and 2-deoxyglycosides of hindered alcohols, aryl thiols, and aryl sulfonamides from glycal derivatives under the Ferrier rearrangement conditions. Product yields and stereo-outcomes were very good.

  四氟硼酸亚硝基酯 (NOBF4) 已成功用作有效的有机催化剂，用于在费里尔重排条件下由糖基衍生物制备受阻醇、芳基硫醇和芳基磺酰胺的 2,3-不饱和和 2-脱氧糖苷。产品产量和立体效果非常好。
• An Efficient Method for the Synthesis of 2,3-Unsaturated Glycopyranosides Catalyzed by Bismuth Trichloride in Ferrier Rearrangement
  作者：N. Raghavendra Swamy、Y. Venkateswarlu

  DOI：10.1055/s-2002-23551

  日期：——

  The reaction of tri-O-acetyl-D-glucal and tri-O-benzyl-D-glucal with various alcohols and thiols to afford the corresponding glycopyranosides in excellent yields by bismuth trichloride in acetonitrile at ambient temperature has been demonstrated.

  已经证明三-O-乙酰基-D-葡糖醛和三-O-苄基-D-葡糖醛与各种醇和硫醇反应，在环境温度下通过乙腈中的三氯化铋以优异的产率提供相应的吡喃糖苷。
• Masson; Soto; Bessodes, Synlett, 2000, # 9, p. 1281 - 1282
  作者：Masson、Soto、Bessodes

  DOI：——

  日期：——
• Zn(OTf)2-Catalyzed Glycosylation of Glycals: Synthesis of 2,3-Unsaturated Glycosides via a Ferrier Reaction
  作者：Palakodety Radha Krishna、Sudhir Kashyap、Gundeboina Narasimha、Batthula Srinivas

  DOI：10.1055/s-0033-1340552

  日期：——

  A mild, catalytic, and efficient protocol has been developed for the synthesis of 2,3-unsaturated glycosides or pseudo-glycals' using Zn(OTf)(2). Stereoselective glycosylation of glycal donor with various acceptors comprising of alcohols, phenols, thiols, and sugar aglycones proceeds smoothly to afford the corresponding 2,3-unsaturaed glycosides in good to excellent yields.