O-benzyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside | 31281-76-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: O-benzyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside
• 英文别名: benzyl-(tetra-O-acetyl-α-D-glucopyranoside)；Benzyl-(tetra-O-acetyl-α-D-glucopyranosid)；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-phenylmethoxyoxan-2-yl]methyl acetate
• CAS: 31281-76-2
• 化学式: C₂₁H₂₆O₁₀
• 分子量: 438.431
• InChiKey: XDMACMMTPGFUCZ-ADAARDCZSA-N

物化性质

• 沸点：
  498.6±45.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  31
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  O-benzyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 生成 methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  COLLINS, P. M.;PREMARATNE, P.;MANRO, A.;HUSSAIN, A., TETRAHEDRON LETT., 30,(1989) N5, C. 4721-4722

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲基 BETA-D-吡喃葡萄糖苷 2,3,4,6-四乙酸酯 在 氯仿 、 四氯化钛 作用下， 生成 O-benzyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside
  参考文献：
  名称：

  Lindberg, Acta Chemica Scandinavica (1947), 1948, vol. 2, p. 426,427

  摘要：

  DOI：

文献信息

• Dibromination of benzyloxy-groups: Glycosyl bromides from benzyl glycosides
  作者：P.M. Collins、P. Premaratne、A. Manro、A. Hussain

  DOI：10.1016/s0040-4039(01)80784-x

  日期：1989.1

  derivatives with bromotrichloromethane and ultraviolet light rapidly gives α-bromobenzyloxy sugars. On further irradiation α,α-dibromobenzyloxy derivatives are formed from benzyl sugar ethers, whereas glycosyl bromides are produced from benzyl furanosides and pyranosides.

  用溴代三氯甲烷和紫外线将糖衍生物中的苄氧基溴化，可快速制得α-溴苄氧基糖。在进一步辐射下，由苄基糖醚形成α，α-二溴苄氧基衍生物，而由苄基呋喃糖苷和吡喃糖苷生产糖基溴化物。
• Glycosylation in Ionic Liquids
  作者：Zbigniew Pakulski

  DOI：10.1055/s-2003-41446

  日期：——

  Glycosyl trichloroacetimidates react smoothly in the presence of trimethylsilyl trifluoromethanesulfonate as a catalyst with a variety of alcohols and monosaccharides in [bmim]PF6 (1-butyl-3-methylimidazolium hexafluorophosphate) as a solvent to afford the corresponding glycosides or disaccharides.

  糖苷三氯乙酰亚胺在三甲基硅醇三氟甲磺酸盐作为催化剂的存在下，与多种醇和单糖在[bmim]PF6（1-丁基-3-甲基咪唑铵六氟磷酸盐）作为溶剂平稳反应，从而得到相应的糖苷或二糖。
• Efficient glycosylation of unprotected sugars using sulfamic acid: A mild eco-friendly catalyst
  作者：Goutam Guchhait、Anup Kumar Misra

  DOI：10.1016/j.catcom.2011.07.016

  日期：2011.10

  Sulfamic acid, a mild and environmentally benign catalyst has been successfully used in the Fischer glycosylation of unprotected sugars for the preparation alkyl glycosides. A diverse range of aliphatic alcohols have been used to prepare a series of alkyl glycosides in good to excellent yield. (C) 2011 Elsevier B.V. All rights reserved.
• Glycosyl iodides. History and recent advances
  作者：Peter J. Meloncelli、Alan D. Martin、Todd L. Lowary

  DOI：10.1016/j.carres.2009.02.032

  日期：2009.6

  The use of glycosyl iodides as an effective method for the preparation of glycosides has had a recent resurgence in carbohydrate chemistry, despite its early roots in which these species were believed to be of limited use. Renewed interest in these species as glycosylating agents has been spurred by their demonstrated utility in the stereoselective preparation of O-glycosides, and other glycosylic compounds. This review provides a brief historical account followed by an examination of the use of glycosyl iodides in the synthesis of oligosaccharicles and other glycomimetics, including C-glycosylic compounds, glycosyl azides and N-glycosides. (C) 2009 Elsevier Ltd. All rights reserved.
• Nagarejan; Jagan Mohan Rao; Gunidutt, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1998, vol. 37, # 2, p. 132 - 134
  作者：Nagarejan、Jagan Mohan Rao、Gunidutt

  DOI：——

  日期：——