cyclopentyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside | 67400-08-2

• 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: cyclopentyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• 英文别名: β-D-Cyclopentylglucopyranosid-tetraacetat；cyclopentyl-(tetra-O-acetyl-β-D-glucopyranoside)；Cyclopentyl-(tetra-O-acetyl-β-D-glucopyranosid)；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-cyclopentyloxyoxan-2-yl]methyl acetate
• CAS: 67400-08-2
• 化学式: C₁₉H₂₈O₁₀
• 分子量: 416.425
• InChiKey: MBLIDCFUUWKFPW-UJWQCDCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.03
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  123.66
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  cyclopentyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 氯仿 、 四氯化钛 作用下， 生成 cyclopentyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside
  参考文献：
  名称：

  Lindberg, Acta Chemica Scandinavica (1947), 1949, vol. 3, p. 151,152

  摘要：

  DOI：
• 作为产物：
  描述：

  环戊醇 、 2,3,4,6-四邻乙酰基-alpha-d-吡喃葡萄糖三氯乙酰胺 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以66%的产率得到cyclopentyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Acceptor site recognition of transglycosylase inhibitors a β-D-glucopyranosyl-(1→2)-α-D-glucopyranuronamide-derived moenomycin analogue

  摘要：

  The synthesis, the antibiotic and the transglycosylase inibiting properties of a disaccharide analogue of moenomycin A in which the NHAc group of unit E is replaced by a hydroxyl function are described. It can be concluded that this NHAc group is essential for eliciting transglycosylase inhibiting properties, in agreement with a recently established solution structure of moenomycin A. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01181-8

文献信息

• 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.