methyl 2,3-bis-O-<(trifluoromethyl)sulfonyl>-4,6-O-(phenylmethylene)-α-D-glucopyranoside | 126456-16-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 2,3-bis-O-<(trifluoromethyl)sulfonyl>-4,6-O-(phenylmethylene)-α-D-glucopyranoside
• 英文别名: methyl 2,3-bis-O-[(trifluoromethyl)sulfonyl]-4,6-O-(phenylmethylene)-α-D-glucopyranoside；[(2R,4aR,6S,7R,8S,8aR)-6-methoxy-2-phenyl-7-(trifluoromethylsulfonyloxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] trifluoromethanesulfonate
• CAS: 126456-16-4
• 化学式: C₁₆H₁₆F₆O₁₀S₂
• 分子量: 546.419
• InChiKey: ODXUIYBUXIMRTI-WNWFYDSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  methyl 2,3-bis-O-<(trifluoromethyl)sulfonyl>-4,6-O-(phenylmethylene)-α-D-glucopyranoside 在 四丁基碘化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以27%的产率得到(2R,4aR,6S,8aS)-(+)-6-methoxy-2-phenyl-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxine
  参考文献：
  名称：

  Efficient Two-Step Multifunctionalization of Substituted 2-Hydro­xyglycopyranosides

  摘要：

  A straightforward route to diversely functionalized glycopyranosides is reported. 2,3-Enopyranosides, 2- and/or 3-azido-, 2-halopyranosides, and a hex-3-ulose, among other - and -glycopyranosides are easily obtained in good to excellent yields from 2-hydroxyglycopyranosides by means of a two-step process involving trifluoromethanesulfonation and subsequent treatment with the appropriate nucleophilic agent.

  DOI：

  10.1055/s-0036-1588624
• 作为产物：
  描述：

  苯甲醛二甲缩醛 在 吡啶 、 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， -30.0~60.0 ℃ 、24.0 kPa 条件下， 反应 3.0h， 生成 methyl 2,3-bis-O-<(trifluoromethyl)sulfonyl>-4,6-O-(phenylmethylene)-α-D-glucopyranoside
  参考文献：
  名称：

  A facile synthesis of 4,6-O-benzylidene glucal

  摘要：

  4,6-O-Benzylidene protected D-glucal, a useful synthetic intermediate, may be accessed from the extremely cheap and readily available starting material alpha-methyl glucopyranoside, via a simple four-step reaction sequence involving selective triflation and iodide displacement at C-2. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00288-x

文献信息

• Carbohydrate-based N-heterocyclic carbenes for enantioselective catalysis
  作者：Alexander S. Henderson、John F. Bower、M. Carmen Galan

  DOI：10.1039/c4ob02056a

  日期：——

  Versatile syntheses of C2-linked and C2-symmetric carbohydrate-based imidazol(in)ium salts from functionalised amino-carbohydrate derivatives are reported. The novel NHCs were ligated to [Rh(COD)Cl]2 and evaluated in Rh-catalysed asymmetric hydrosilylation of ketones with good yields and promising enantioselectivities.

  报道了从官能化的氨基碳水化合物衍生物多功能合成C 2连接的和C 2对称的基于碳水化合物的咪唑盐。将新型NHC连接到[Rh（COD）Cl] 2上，并在Rh催化的酮的不对称氢化硅烷化中进行了评估，产率高，对映选择性高。
• Amino alcohol and amino sugar synthesis by benzoylcarbamate cyclization
  作者：Spencer Knapp、Paivi J. Kukkola、Shashi Sharma、T. G. Murali Dhar、Andrew B. J. Naughton

  DOI：10.1021/jo00309a013

  日期：1990.10
• Efficient Two-Step Multifunctionalization of Substituted 2-Hydro­xyglycopyranosides
  作者：Antonio Franconetti、Francisca Cabrera-Escribano、Eleuterio Álvarez

  DOI：10.1055/s-0036-1588624

  日期：——

  A straightforward route to diversely functionalized glycopyranosides is reported. 2,3-Enopyranosides, 2- and/or 3-azido-, 2-halopyranosides, and a hex-3-ulose, among other - and -glycopyranosides are easily obtained in good to excellent yields from 2-hydroxyglycopyranosides by means of a two-step process involving trifluoromethanesulfonation and subsequent treatment with the appropriate nucleophilic agent.
• A facile synthesis of 4,6-O-benzylidene glucal
  作者：David J. Chambers、Graham R. Evans、Antony J. Fairbanks

  DOI：10.1016/s0957-4166(03)00288-x

  日期：2003.7

  4,6-O-Benzylidene protected D-glucal, a useful synthetic intermediate, may be accessed from the extremely cheap and readily available starting material alpha-methyl glucopyranoside, via a simple four-step reaction sequence involving selective triflation and iodide displacement at C-2. (C) 2003 Elsevier Science Ltd. All rights reserved.