isopropyl β-D-mannopyranoside | 73351-02-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: isopropyl β-D-mannopyranoside
• 英文别名: isopropyl-D-mannopyranoside；(2R,3S,4S,5S,6R)-2-(hydroxymethyl)-6-propan-2-yloxyoxane-3,4,5-triol
• CAS: 73351-02-7
• 化学式: C₉H₁₈O₆
• 分子量: 222.238
• InChiKey: UOEFDXYUEPHESS-XGQMLPDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 isopropyl β-D-mannopyranoside 在 吡啶 作用下， 以66 mg的产率得到iso-propyl 2,3,4,6-tetra-O-acetyl-β-D-mannopyranoside
  参考文献：
  名称：

  Experimental evidence on the hydroxymethyl group conformation in alkyl β-d-mannopyranosides

  摘要：

  A rotational population Study of the hydroxymethyl group of alkyl beta-D-mannopyranosides was performed by means of CD and NMR spectroscopy. Three different benzyl, acetyl, and p-bromobenzoyl series of alkyl beta-D-mannopyranosides with different chiral and nonchiral aglycons were synthesized and analyzed. Different rotational populations were observed for each series by changing the structure of the aglycon. The results showed a clear correlation between the rotational population of the hydroxymethyl group around the C5-C6 bond and the pK(a) of the bonded alcohol (aglycon). The population of the gt rotamer gradually increased as the pK(a) increased while that of the gg rotamer decreased and the population of the tg rotamer remained almost constant. This is explained by the exo-anomeric effect. For chiral alkyl derivatives, the results also showed a close dependence on the absolute configuration of the aglycon. Comparison of rotational population anomers revealed the dependence or the hydroxymethyl group on the anomeric configuration and a greater dependence on the aglycon structure in the beta anomers. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.06.019
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-1,2-O-(S)-(1-ethoxyethylidene)-α-D-glucopyranose 在 palladium on activated charcoal 吡啶 、 氢氧化钾 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 3 A molecular sieve 、 氢气 、 silver carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 11.54h， 生成 isopropyl β-D-mannopyranoside
  参考文献：
  名称：

  3,4,6-Tri-O-benzyl-.alpha.-D-arabino-hexopyranos-2-ulosyl Bromide: A Versatile Glycosyl Donor for the Efficient Generation of .beta.-D-Mannopyranosidic Linkages

  摘要：

  An expedient four-step sequence is described for the conversion of acetobromoglucose into the title 2-oxohexosyl (''ulosyl'') bromide 4. Due to its O-benzyl protection, 4 is considerably more reactive than its acylated analogs 1-3: Ag2CO3-promoted glycosidations with 2-propanol, diacetone-galactose, and methyl 2,3-O-isopropylidene-alpha-L-rhamnoside are complete within minutes and, in addition, are endowed with beta-specificity. This renders ulosyl bromide 4 a most propitious, indirect beta-D-mannosyl donor, inasmuch as the borohydride reduction of the beta-D-glycosiduloses formed (14-16 --> 19, 21, and 22) proceeds with manno selectivities of >20:1. Comparative evaluation of the manno/gluco ratios obtained in all 21 beta-D-arabino hexosidulose reductions (Table 1) reveals the 3-O-blocking group to have a pronounced effect on the outcome: >20:1 in cases with a 3-O-benzyl group versus only 2:1 to 3:1 in the presence of 3-O-acyl functions.

  DOI：

  10.1021/jo00101a035

文献信息

• Metal-catalyzed Stereoselective and Protecting-group-free Synthesis of 1,2-<i>cis</i>-Glycosides Using 4,6-Dimethoxy-1,3,5-triazin-2-yl Glycosides as Glycosyl Donors
  作者：Tomonari Tanaka、Naoya Kikuta、Yoshiharu Kimura、Shin-ichiro Shoda

  DOI：10.1246/cl.150201

  日期：2015.6.5

  4,6-Dimethoxy-1,3,5-triazin-2-yl glycosides, glycosyl donors prepared in one step from free saccharides without protection of the hydroxy groups, were stereoselectively and equivalently converted t...

  4,6-二甲氧基-1,3,5-triazin-2-yl 糖苷，由游离糖一步制备的糖基供体，没有羟基保护，立体选择性地等价转化为...
• Enzymatic Synthesis of Alkyl and Hydroxyalkyl β-D-Mannopyranosides
  作者：N. Taubken、J. Thiem

  DOI：10.1055/s-1992-26148

  日期：——

  The preparation of anomerically pure alkyl and hydroxyalkyl ß-mannopyranosides 3a-h by using the transfer activity of ß-mannohydrolase [EC 3.2.1.25] is described.

  本文介绍了利用ß-甘露糖苷酶[EC 3.2.1.25]的转移活性制备异构纯烷基和羟烷基ß-甘露糖苷 3a-h 的方法。
• 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.
• Organocatalyzed Direct Glycosylation of Unprotected and Unactivated Carbohydrates
  作者：Sebastian Schmalisch、Rainer Mahrwald

  DOI：10.1021/ol402914v

  日期：2013.11.15

  Organocatalyzed direct glycosylation of unprotected and unactivated carbohydrates is reported. This process is catalyzed by triphenylphosphine and tetrabromomethane at room temperature under neutral conditions. With this operationally simple protocol thermodynamically favored, glycosides were obtained in a very straightforward reaction.
• Experimental evidence on the hydroxymethyl group conformation in alkyl β-d-mannopyranosides
  作者：Carlos Mayato、Rosa Dorta、Jesús Vázquez

  DOI：10.1016/j.tetasy.2004.06.019

  日期：2004.8

  A rotational population Study of the hydroxymethyl group of alkyl beta-D-mannopyranosides was performed by means of CD and NMR spectroscopy. Three different benzyl, acetyl, and p-bromobenzoyl series of alkyl beta-D-mannopyranosides with different chiral and nonchiral aglycons were synthesized and analyzed. Different rotational populations were observed for each series by changing the structure of the aglycon. The results showed a clear correlation between the rotational population of the hydroxymethyl group around the C5-C6 bond and the pK(a) of the bonded alcohol (aglycon). The population of the gt rotamer gradually increased as the pK(a) increased while that of the gg rotamer decreased and the population of the tg rotamer remained almost constant. This is explained by the exo-anomeric effect. For chiral alkyl derivatives, the results also showed a close dependence on the absolute configuration of the aglycon. Comparison of rotational population anomers revealed the dependence or the hydroxymethyl group on the anomeric configuration and a greater dependence on the aglycon structure in the beta anomers. (C) 2004 Elsevier Ltd. All rights reserved.