benzyl α-D-rhamnopyranoside | 191546-20-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl α-D-rhamnopyranoside
• 英文别名: (2R,3S,4S,5S,6S)-2-methyl-6-phenylmethoxyoxane-3,4,5-triol
• CAS: 191546-20-0
• 化学式: C₁₃H₁₈O₅
• 分子量: 254.283
• InChiKey: UHQDDNIUJBFOEL-WSLQDRLSSA-N

物化性质

• 沸点：
  419.2±45.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl α-D-rhamnopyranoside 在 吡啶 、 sodium azide 、 叠氮基三甲基硅烷 、 三氟化硼乙醚 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 5.67h， 生成 benzyl 4-azido-2-O-benzoyl-4-deoxy-α-D-rhamnopyranoside
  参考文献：
  名称：

  An efficient synthesis of selectively functionalized d-rhamnose derivatives

  摘要：

  D-Rhamnose is an important component of bacterial lipopolysaccharides. This paper describes a short and highly efficient synthesis of D-rhamnose from D-mannose. The synthesis of selectively C-4 modified D-rhamnosides and 6-deoxy-D-talosides as potential building blocks for complex oligosaccharide synthesis is also discussed. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.064
• 作为产物：
  描述：

  甘露糖 在 吡啶 、 盐酸 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 11.0h， 生成 benzyl α-D-rhamnopyranoside
  参考文献：
  名称：

  On the regioselectivity of the protease subtilisin towards the acylation of enantiomeric pairs of benzyl and naphthyl glycopyranosides. Part 2

  摘要：

  Subtilisin-catalyzed esterification of several enantiomeric benzyl and naphthyl glycopyranosides has been investigated. The D-sugar derivatives were all good substrates and subtilisin regioselectivity was similar with all the compounds tested, the 3-OH being acylated predominantly. On the other hand, most of the L-glycopyranosides were transformed during longer reaction times with a lower regioselectivity, the 2-OH being preferentially but not exclusively acylated. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01217-4

文献信息

• Efficient Enzymatic Synthesis of Guanosine 5′-Diphosphate-Sugars and Derivatives
  作者：Lei Li、Yonghui Liu、Yue Wan、Yanhong Li、Xi Chen、Wei Zhao、Peng George Wang

  DOI：10.1021/ol402585c

  日期：2013.11

  Bifidobacterium infantis (NahK_15697), a guanosine 5′-diphosphate (GDP)-mannose pyrophosphorylase from Pyrococcus furiosus (PFManC), and an Escherichia coli inorganic pyrophosphatase (EcPpA) were used efficiently for a one-pot three-enzyme synthesis of GDP-mannose, GDP-glucose, their derivatives, and GDP-talose. This study represents the first facile and efficient enzymatic synthesis of GDP-sugars and derivatives

  来自婴儿双歧杆菌的N-乙酰己糖胺 1-激酶(NahK_15697)、来自激烈火球菌(PFManC)的鸟苷 5'-二磷酸 (GDP)-甘露糖焦磷酸化酶和大肠杆菌无机焦磷酸酶 (EcPpA) 被有效地用于一锅GDP-甘露糖、GDP-葡萄糖及其衍生物和GDP-塔糖的三酶合成。这项研究代表了从单糖和衍生物开始的 GDP 糖和衍生物的首次简便有效的酶促合成。
• On the regioselectivity of the protease subtilisin towards the acylation of enantiomeric pairs of benzyl and naphthyl glycopyranosides. Part 2
  作者：Bruno Danieli、Francesco Peri、Gabriella Roda、Giacomo Carrea、Sergio Riva

  DOI：10.1016/s0040-4020(98)01217-4

  日期：1999.2

  Subtilisin-catalyzed esterification of several enantiomeric benzyl and naphthyl glycopyranosides has been investigated. The D-sugar derivatives were all good substrates and subtilisin regioselectivity was similar with all the compounds tested, the 3-OH being acylated predominantly. On the other hand, most of the L-glycopyranosides were transformed during longer reaction times with a lower regioselectivity, the 2-OH being preferentially but not exclusively acylated. (C) 1999 Elsevier Science Ltd. All rights reserved.
• WO2023/168520
  申请人：——

  公开号：——

  公开（公告）日：——
• An efficient synthesis of selectively functionalized d-rhamnose derivatives
  作者：Matthew Zunk、Milton J. Kiefel

  DOI：10.1016/j.tetlet.2011.01.064

  日期：2011.3

  D-Rhamnose is an important component of bacterial lipopolysaccharides. This paper describes a short and highly efficient synthesis of D-rhamnose from D-mannose. The synthesis of selectively C-4 modified D-rhamnosides and 6-deoxy-D-talosides as potential building blocks for complex oligosaccharide synthesis is also discussed. (C) 2011 Elsevier Ltd. All rights reserved.