1-formyl-β-D-glucopyranoside | 791097-02-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-formyl-β-D-glucopyranoside
• 英文别名: (2R,3R,4S,5S,6R)-2-(dihydroxymethyl)-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 791097-02-4
• 化学式: C₇H₁₄O₇
• 分子量: 210.184
• InChiKey: MLVVQHVRFPYEOI-VFUOTHLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  131
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 3-溴丙烯 、 1-formyl-β-D-glucopyranoside 在 indium 、 吡啶 作用下， 以 四氢呋喃 、 水 为溶剂， 以85%的产率得到Acetic acid (2S,3S,4S,5R,6R)-4,5-diacetoxy-2-(1-acetoxy-but-3-enyl)-6-acetoxymethyl-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  New and general synthesis of β-C-glycosylformaldehydes from easily available β-C-glycosylpropanones

  摘要：

  A highly effective method for the introduction of a formyl group at the anomeric position of pyranosides was developed via enolisation Of beta-C-D-glycopyranosylpropan-2-one using thermodynamic conditions then oxidative cleavage of the more substituted double bond. This sequence affords the desired aldehydes that are conveniently protected as aminals for purification and storage and easily regenerated using Dowex resin H+. In this paper, the syntheses of nine differently protected aldehydes derived from D-glucose, D-galactose. lactose and N-acetyl-D-glucosamine are presented. Our strategy proved to be very efficient in most cases excepted in the D-mannose series. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.09.002
• 作为产物：
  描述：

  1-(β-D-glucopyranosyl)propan-2-one 在 吡啶 、 sodium periodate 、 Dowex-H+ resin 、 sodium methylate 、 二甲基二环氧乙烷 、 potassium carbonate 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丙酮 、 甲苯 为溶剂， 生成 1-formyl-β-D-glucopyranoside
  参考文献：
  名称：

  A convenient new route to protected and free 2,6-anhydro-d-glycero-d-gulo-heptoses (1-formyl-β-d-glucopyranosides)

  摘要：

  A new and efficient process has been developed for the synthesis of 1-formyl-beta-D-glucopyranosides frorn D-glucose. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.08.034

文献信息

• New and general synthesis of β-C-glycosylformaldehydes from easily available β-C-glycosylpropanones
  作者：Stéphanie Norsikian、Jennifer Zeitouni、Stéphanie Rat、Sylvie Gérard、André Lubineau

  DOI：10.1016/j.carres.2007.09.002

  日期：2007.12

  A highly effective method for the introduction of a formyl group at the anomeric position of pyranosides was developed via enolisation Of beta-C-D-glycopyranosylpropan-2-one using thermodynamic conditions then oxidative cleavage of the more substituted double bond. This sequence affords the desired aldehydes that are conveniently protected as aminals for purification and storage and easily regenerated using Dowex resin H+. In this paper, the syntheses of nine differently protected aldehydes derived from D-glucose, D-galactose. lactose and N-acetyl-D-glucosamine are presented. Our strategy proved to be very efficient in most cases excepted in the D-mannose series. (C) 2007 Elsevier Ltd. All rights reserved.
• A convenient new route to protected and free 2,6-anhydro-d-glycero-d-gulo-heptoses (1-formyl-β-d-glucopyranosides)
  作者：Jennifer Zeitouni、Stéphanie Norsikian、André Lubineau

  DOI：10.1016/j.tetlet.2004.08.034

  日期：2004.10

  A new and efficient process has been developed for the synthesis of 1-formyl-beta-D-glucopyranosides frorn D-glucose. (C) 2004 Elsevier Ltd. All rights reserved.