tert-butyl N-[3-[(2R,3R,4R,5R,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxypropyl]carbamate | 769120-27-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl N-[3-[(2R,3R,4R,5R,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxypropyl]carbamate
• CAS: 769120-27-6
• 化学式: C₂₀H₃₇NO₁₃
• 分子量: 499.513
• InChiKey: LCOWKJGLYTVIER-OANJZRBMSA-N

物化性质

• 沸点：
  755.8±60.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  217
• 氢给体数：
  8
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  溴甲苯 、 tert-butyl N-[3-[(2R,3R,4R,5R,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxypropyl]carbamate 在 二正丁基氧化锡 、 四丁基碘化铵 作用下， 以 乙腈 、 苯 为溶剂， 反应 0.25h， 以80%的产率得到{3-[(2R,3R,4R,5R,6R)-5-((2R,3R,4S,5S,6R)-4-Benzyloxy-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-3,4-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy]-propyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Microwave-assisted, tin-mediated, regioselective 3-O-alkylation of galactosides

  摘要：

  A rapid, efficient and versatile microwave-assisted dibutylstannylene-mediated 3-O-alkylation method for galactosides was established. The alkylation reaction was significantly enhanced by microwave irradiation and allowed the use of an alkylating agent too unstable for incorporation using conventional heating. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.06.113
• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 Lindlar's catalyst 三乙基硅烷 、 sodium azide 、 三氟甲磺酸三甲基硅酯 、 三氟化硼乙醚 、 氢气 、 sodium methylate 、 sodium hydride 、 对甲苯磺酸 、 溶剂黄146 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.5h， 生成 tert-butyl N-[3-[(2R,3R,4R,5R,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxypropyl]carbamate
  参考文献：
  名称：

  Inhibition of Streptococcus suis Adhesion by Dendritic Galabiose Compounds at Low Nanomolar Concentration

  摘要：

  A series of mono-, di-, and tetravalent galablose (Ga1alpha1-4Gal) compounds were synthesized in good yields by coupling of a general carboxylic acid-bearing sugar building block to dendritic scaffolds based on the 3,5-di-(2-aminoethoxy)benzoic acid branching unit. Furthermore. a poly(amidoamine)- (PAMAM-) based dendritic galabioside was Synthesized containing eight galabiose units. All galabiosides were tested in a hemagglutination assay and a Surface plasmon resonance (SPR) competition assay in order to establish their potency in the binding to the bacterial Gram-positive pathogen Streptococcus suis. A monovalent cralabioside containing a short spacer was used as a reference compound in all the assays. Varations in the scaffold as well as in the spacer arms were introduced to determine their influence on the inhibition. The best inhibitor of hemagglutination was an octavalent galabioside with a minimal inhibitory concentration (MIC) of 0.3 nM, to the best of our knowledge the first, example of inhibition of bacterial binding by a soluble carbohydrate at a subnanomolar concentration.

  DOI：

  10.1021/jm049476+

文献信息

• Inhibition of <i>Streptococcus </i><i>s</i><i>uis</i> Adhesion by Dendritic Galabiose Compounds at Low Nanomolar Concentration
  作者：John A. F. Joosten、Vuokko Loimaranta、Chantal C. M. Appeldoorn、Sauli Haataja、Fatna Ait El Maate、Rob M. J. Liskamp、Jukka Finne、Roland J. Pieters

  DOI：10.1021/jm049476+

  日期：2004.12.1

  A series of mono-, di-, and tetravalent galablose (Ga1alpha1-4Gal) compounds were synthesized in good yields by coupling of a general carboxylic acid-bearing sugar building block to dendritic scaffolds based on the 3,5-di-(2-aminoethoxy)benzoic acid branching unit. Furthermore. a poly(amidoamine)- (PAMAM-) based dendritic galabioside was Synthesized containing eight galabiose units. All galabiosides were tested in a hemagglutination assay and a Surface plasmon resonance (SPR) competition assay in order to establish their potency in the binding to the bacterial Gram-positive pathogen Streptococcus suis. A monovalent cralabioside containing a short spacer was used as a reference compound in all the assays. Varations in the scaffold as well as in the spacer arms were introduced to determine their influence on the inhibition. The best inhibitor of hemagglutination was an octavalent galabioside with a minimal inhibitory concentration (MIC) of 0.3 nM, to the best of our knowledge the first, example of inhibition of bacterial binding by a soluble carbohydrate at a subnanomolar concentration.
• Microwave-assisted, tin-mediated, regioselective 3-O-alkylation of galactosides
  作者：Lluis Ballell、John A.F. Joosten、Fatna Ait el Maate、Rob M.J. Liskamp、Roland J. Pieters

  DOI：10.1016/j.tetlet.2004.06.113

  日期：2004.8

  A rapid, efficient and versatile microwave-assisted dibutylstannylene-mediated 3-O-alkylation method for galactosides was established. The alkylation reaction was significantly enhanced by microwave irradiation and allowed the use of an alkylating agent too unstable for incorporation using conventional heating. (C) 2004 Elsevier Ltd. All rights reserved.