(1-adamantanyl) 3,6-di-O-benzyl-2-O-(p-toluenesulfonyl)-β-D-mannopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1-adamantanyl) 3,6-di-O-benzyl-2-O-(p-toluenesulfonyl)-β-D-mannopyranoside
• 英文别名: [(2S,3S,4S,5R,6R)-2-(1-adamantyloxy)-5-hydroxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl] 4-methylbenzenesulfonate
• 化学式: C₃₇H₄₄O₈S
• 分子量: 648.818
• InChiKey: ISTTZYAJGQHLTP-KLSRTSPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  46
• 可旋转键数：
  12
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  S-phenyl 3-O-benzyl-4,6-O-benzylidene-β-D-thiomannopyranoside 在 2,4,6-三甲基吡啶 、 2,4,6-三甲基嘧啶 、 二苯基亚砜 、 sodium cyanoborohydride 、 trifluoromethanesulfonic acid anhydride 、 三乙胺 、 potassium iodide 、 silver(l) oxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 31.08h， 生成 (1-adamantanyl) 3,6-di-O-benzyl-2-O-(p-toluenesulfonyl)-β-D-mannopyranoside
  参考文献：
  名称：

  Disarming, non-participating 2-O-protecting groups in manno- and rhamnopyranosylation: scope and limitations of sulfonates, vinylogous esters, phosphates, cyanates, and nitrates

  摘要：

  A series of D-mannopyranosyl and L-rhamnopyranosyl thioglycosides; protected with electron-withdrawing non-participating protecting groups on O-2 have been prepared and investigated for their potential as beta-glycosyl donors. Both alpha- and beta-thioglycosides were investigated and the latter preferred on the grounds of enhanced stability at room temperature. A 2-O-nitro-L-rhamnosyl fluoride was also prepared and investigated. Moderate beta-selectivities were observed with some of these donors. With the more powerfully electron-withdrawing groups reduced donor reactivity leads to a requirement for higher reaction temperatures and reduced selectivities. Decomposition temperatures of the intermediate glycosyl triflates were determined by variable temperature NMR spectroscopy and generally correlate with the disarming propensity of the protecting group system. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.032

文献信息

• Disarming, non-participating 2-O-protecting groups in manno- and rhamnopyranosylation: scope and limitations of sulfonates, vinylogous esters, phosphates, cyanates, and nitrates
  作者：David Crich、Thomas K. Hutton、Abhisek Banerjee、Prasanna Jayalath、John Picione

  DOI：10.1016/j.tetasy.2004.11.032

  日期：2005.1

  A series of D-mannopyranosyl and L-rhamnopyranosyl thioglycosides; protected with electron-withdrawing non-participating protecting groups on O-2 have been prepared and investigated for their potential as beta-glycosyl donors. Both alpha- and beta-thioglycosides were investigated and the latter preferred on the grounds of enhanced stability at room temperature. A 2-O-nitro-L-rhamnosyl fluoride was also prepared and investigated. Moderate beta-selectivities were observed with some of these donors. With the more powerfully electron-withdrawing groups reduced donor reactivity leads to a requirement for higher reaction temperatures and reduced selectivities. Decomposition temperatures of the intermediate glycosyl triflates were determined by variable temperature NMR spectroscopy and generally correlate with the disarming propensity of the protecting group system. (C) 2004 Elsevier Ltd. All rights reserved.