phenyl 3-O-pivaloyl-4,6-O-benzylidene-1-seleno-β-D-glucopyranoside | 247152-88-1

• 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: phenyl 3-O-pivaloyl-4,6-O-benzylidene-1-seleno-β-D-glucopyranoside
• 英文别名: [(2R,4aR,6S,7R,8R,8aR)-7-hydroxy-2-phenyl-6-phenylselanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] 2,2-dimethylpropanoate
• CAS: 247152-88-1
• 化学式: C₂₄H₂₈O₆Se
• 分子量: 491.443
• InChiKey: MCVXCVVZIIGVNS-ILHTXMRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenyl 3-O-pivaloyl-4,6-O-benzylidene-1-seleno-β-D-glucopyranoside 在 二甲基亚砜 、 三乙胺 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 生成 2,2-Dimethyl-propionic acid (2R,4aR,6S,8S,8aR)-7-oxo-2-phenyl-6-phenylselanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester
  参考文献：
  名称：

  含有α-连接的GlcNAc或β-连接的ManNAc单元的二糖的合成

  摘要：

  描述了由稳定的，但仍具有高反应性的2-氧亚氨基糖基供体合成含有α-连接的GlcNAc或β-连接的ManNAc单元的二糖。通过仔细选择溶剂和糖苷化条件，可以获得占优势的含有α-连接的GlcNAc或β-连接的ManNAc单元的二糖。

  DOI：

  10.1016/s0040-4020(01)00760-8
• 作为产物：
  描述：

  三甲基乙酰氯 、 phenyl (5R)-4,6-O-benzylidene-1-seleno-β-D-glucopyranoside 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 25.17h， 以39%的产率得到phenyl 3-O-pivaloyl-4,6-O-benzylidene-1-seleno-β-D-glucopyranoside
  参考文献：
  名称：

  Regioselective C-3-O-acylation and O-alkylation of 4,6-O-benzylidene-β-d-glucopyranoside, derivatives displaying a range of anomeric substituents

  摘要：

  Regioselective C-3-O-acylation and O-alkylation of ethyl 4,6-O-benzylidene-1-thio-beta-D-glucopyranoside, phenyl 4,6-O-benzylidene-beta-D-glucopyranoside and phenyl 4,6-O-benzylidene-1-seleno-beta-D-glucopyranoside is described. Regioselectivity is obtained by first treating the benzylidene diols with sodium hydride and copper (II) chloride to form a THF soluble copper chelate. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01420-3

文献信息

• Regioselective C-3-O-acylation and O-alkylation of 4,6-O-benzylidene-β-d-glucopyranoside, derivatives displaying a range of anomeric substituents
  作者：Jonathan J. Gridley、Helen M.I. Osborn、William G. Suthers

  DOI：10.1016/s0040-4039(99)01420-3

  日期：1999.9

  Regioselective C-3-O-acylation and O-alkylation of ethyl 4,6-O-benzylidene-1-thio-beta-D-glucopyranoside, phenyl 4,6-O-benzylidene-beta-D-glucopyranoside and phenyl 4,6-O-benzylidene-1-seleno-beta-D-glucopyranoside is described. Regioselectivity is obtained by first treating the benzylidene diols with sodium hydride and copper (II) chloride to form a THF soluble copper chelate. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthesis of disaccharides containing α-linked GlcNAc or β-linked ManNAc units
  作者：Michael G.B Drew、Seth C Ennis、Jonathan J Gridley、Helen M.I Osborn、David G Spackman

  DOI：10.1016/s0040-4020(01)00760-8

  日期：2001.9

  The synthesis of disaccharides containing α-linked GlcNAc or β-linked ManNAc units from shelf-stable, and yet highly reactive, 2-oximinoglycosyl donors is described. Access to a preponderance of the disaccharides containing either the α-linked GlcNAc or β-linked ManNAc unit can be obtained by careful choice of solvent and glycosidation conditions.

  描述了由稳定的，但仍具有高反应性的2-氧亚氨基糖基供体合成含有α-连接的GlcNAc或β-连接的ManNAc单元的二糖。通过仔细选择溶剂和糖苷化条件，可以获得占优势的含有α-连接的GlcNAc或β-连接的ManNAc单元的二糖。
• Regioselective C-3-O-acylation and O-methylation of 4,6-O-benzylidene-β-d-gluco- and galactopyranosides displaying a range of anomeric substituents
  作者：Helen M.I Osborn、Victoria A Brome、Laurence M Harwood、William G Suthers

  DOI：10.1016/s0008-6215(01)00063-5

  日期：2001.5

  The regioselective C-3-O-acylation and O-methylation of a range of 4,6-O-benzylidene-beta -D-gluco- and galactopyranosides has been studied. Regioselectivity is achieved by forming the copper chelate of the 2,3-diol using either sodium hydride and copper(II) chloride, or copper(II) acetylacetanoate, or copper(II) acetate, prior to introduction of the acylating or methylating agent. (C) 2001 Elsevier Science Ltd. All rights reserved.