3β-cholestanyl 2,3,4-tri-O-benzyl-β-L-rhamnopyranoside | 129796-70-9

• 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: 3β-cholestanyl 2,3,4-tri-O-benzyl-β-L-rhamnopyranoside
• 英文别名: 3β-cholestanyl 2,3,4-tri-O-benzyl-L-rhamnopyranoside；(2S,3R,4R,5S,6S)-2-[[(3S,5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-methyl-3,4,5-tris(phenylmethoxy)oxane
• CAS: 129796-70-9
• 化学式: C₅₄H₇₆O₅
• 分子量: 805.194
• InChiKey: WDKIGEZEXULORT-YATJVTRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.4
• 重原子数：
  59
• 可旋转键数：
  16
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl chloride 、 3β-胆甾烷醇 生成 3β-cholestanyl 2,3,4-tri-O-benzyl-β-L-rhamnopyranoside
  参考文献：
  名称：

  NISHIZAWA, MUGIO;KAN, YUKIKO;SHIMOMOTO, WAKA;YAMADA, HIDETOSHI, TETRAHEDRON LETT., 31,(1990) N7, C. 2431-2434

  摘要：

  DOI：

文献信息

• New Synthetic Methods and Reagents for Complex Carbohydrates. VIII. Stereoselective<i>α</i>- and<i>β</i>-Mannopyranoside Formation from Glycosyl Dimethylphosphinothioates with the C-2 Axial Benzyloxyl Group
  作者：Takashi Yamanoi、Kazumi Nakamura、Hiroshi Takeyama、Kenji Yanagihara、Toshiyuki Inazu

  DOI：10.1246/bcsj.67.1359

  日期：1994.5

  The reactions of mannopyranosyl dimethylphosphinothioates and alcohols using silver perchlorate as an activator in the presence of molecular sieves 4A in benzene at room temperature gave the 1,2-trans-α-mannopyranosides in good yields. On the other hand, 1,2-cis-β-mannopyranosides could be obtained from the dimethylphosphinothioates by the combined use of iodine and 5 mol% triphenylmethyl perchlorate

  吡喃甘露糖基二甲基硫代膦酸酯和醇使用高氯酸银作为活化剂，在分子筛 4A 存在下，在室温下在苯中反应，以良好的收率得到 1,2-反式-α-吡喃甘露糖苷。另一方面，通过结合使用碘和 5 mol% 高氯酸三苯甲酯作为活化系统，可以从二甲基硫代膦酸酯中获得 1,2-顺式-β-吡喃甘露糖苷。描述了通过这些方法合成糖蛋白的 αMan(1→6)[αMan(1→3)]Man 和 βMan(1→4)GlcNAc 单元的衍生物。
• The 3,4-<i>O</i>-Carbonate Protecting Group as a β-Directing Group in Rhamnopyranosylation in Both Homogeneous and Heterogeneous Glycosylations As Compared to the Chameleon-like 2,3-<i>O</i>-Carbonates
  作者：David Crich、A. U. Vinod、John Picione

  DOI：10.1021/jo035003j

  日期：2003.10.1

  It is demonstrated that the beta-selectivity observed in the insoluble silver salt mediated couplings of 2,3-O-carbonate-protected rhamnosyl bromides is uniquely due to the heterogeneous nature of the reaction. In homogeneous solution these same donors are alpha-selective, a fact that is attributed to the half-chair conformation of these substances which reduces the energy barrier to oxacarbenium ion formation. It is suggested that the 2,3-O-carbonate group be dubbed torsionally arming in the manno- and rhamnopyranose series. When the carbonate group is removed to the 3,4-O-position a beta-selective system is formed, in both homogeneous and heterogeneous conditions, and it is demonstrated that this selectivity arises from the combination of the electron-withdrawing nature of the carbonate and its inability to take part in neighboring participation.
• α-Selective thermal glycosidation of rhamnosyl and mannosyl chlorides
  作者：Mugio Nishizawa、Yukiko Kan、Waka Shimomoto、Hidetoshi Yamada

  DOI：10.1016/s0040-4039(00)97381-7

  日期：1990.1
• NISHIZAWA, MUGIO;KAN, YUKIKO;SHIMOMOTO, WAKA;YAMADA, HIDETOSHI, TETRAHEDRON LETT., 31,(1990) N7, C. 2431-2434
  作者：NISHIZAWA, MUGIO、KAN, YUKIKO、SHIMOMOTO, WAKA、YAMADA, HIDETOSHI

  DOI：——

  日期：——