isopropyl α-D-glucopyranoside | 5391-17-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: isopropyl α-D-glucopyranoside
• 英文别名: isopropyl-α-D-glucopyranoside；2-propyl α-D-glucopyranoside；2-propyl glucoside；1-O-Isopropyl-β-D-glucopyranosid；Isopropyl-α-D-glucopyranosid；α-D-Isopropylglucopyranosid；isopropyl alpha-D-glucopyranoside；(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-propan-2-yloxyoxane-3,4,5-triol
• CAS: 5391-17-3；25320-92-7；40593-10-0；55508-29-7；73351-02-7；124339-98-6
• 化学式: C₉H₁₈O₆
• 分子量: 222.238
• InChiKey: UOEFDXYUEPHESS-ZEBDFXRSSA-N

物化性质

• 沸点：
  395.0±42.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

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

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  isopropyl α-D-glucopyranoside 在 4-二甲氨基吡啶 、 对甲苯磺酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 isopropyl 4,6-O-benzylidene-2,3-di-O-(N-tert-butoxycarbonyl-L-alanyl)-α-D-glucopyranoside
  参考文献：
  名称：

  SYNTHESIS OF AMINOACYL SUGAR DERIVATIVES AND THEIR TASTE CHARACTERISTICS. I. 2,3-DI- O-AMINOACYL DERIVATIVES OF ALKYL d-GLUCOPYRANOSIDES

  摘要：

  Aminoacyl derivatives of methyl alpha- and beta-D-glucopyranosides have been synthesized in order to ascertain the structural features required for the perception of a sweet taste. 2,3-Di-O-(L-aminoacyl) derivatives of methyl alpha-D-glucopyranoside showed a strong sweet taste (16-35x sucrose), which decreased or disappeared when either one of the two L-aminoacyl groups was absent or substituted by a D-aminoacyl group. In the case of 2,3-di-O-(L-alanyl) derivatives of methyl D-glucopyranoside, the a-anomer was very sweet (16-25x suc.) whereas the beta-anomer was not sweet. The structural prerequisite for sweetness in this group of compounds proved to be the presence Of L-aminoacyl groups at C-2 and C-3, and the alpha-configuration at C-1. Its a-isopropyl anomer showed the highest sweetness (64x suc.), hence the increased lipophilicity is also an important criterion.

  DOI：

  10.1081/car-120003744
• 作为产物：
  描述：

  isopropyl 3,4,6-tri-O-benzyl-α-D-glucopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以77%的产率得到isopropyl α-D-glucopyranoside
  参考文献：
  名称：

  Site-Selective Catalysis of Phenyl Thionoformate Transfer as a Tool for Regioselective Deoxygenation of Polyols

  摘要：

  [Graphics]We report the application of peptide-embedded imidazoles as catalysts for the site-selective delivery of the phenyl thionoformate unit as a prelude to deoxygenation reactions of polyols. Methodology was developed that allows for the synthesis of thiocarboryl derivatives based on a combination of additives that include N-alkylimidazoles and FeCl3 as co-catalysts. The use of this reagent combination leads to increased reaction rates and efficient yields relative to those of simple base-mediated reactions. In terms of controlling regioselectivity during the course of polyol modification, we found that histidine-containing peptides, in combination with FeCl3, could lead to modulation of the product distribution. Through screening of peptides and control of reaction conditions, products could be observed that reflected both the inherent preference of substrates and also reversal of inherent selectivity.

  DOI：

  10.1021/jo702334z

文献信息

• Selective C−O Bond Cleavage of Sugars with Hydrosilanes Catalyzed by Piers’ Borane Generated In Situ
  作者：Jianbo Zhang、Sehoon Park、Sukbok Chang

  DOI：10.1002/anie.201708109

  日期：2017.10.23

  [(C6F5)2BH], generated in situ, is demonstrated to promote the hydrosilylative reduction of sugars, providing a series of linear or cyclic polyols with high chemo- and regioselectivities under mild conditions. Studies of catalytic reactivity and regioselectivity with regard to the C−O bond cleavage with hydrosilanes suggest an importance of the steric environment around the anomeric carbon center of the

  Piers的硼烷[（C 6 F 5）2 BH]原位生成，可促进糖的氢化硅烷化还原，在温和条件下提供一系列具有高化学选择性和区域选择性的线性或环状多元醇。关于用氢硅烷裂解C-O键的催化反应性和区域选择性的研究表明，糖异头碳中心周围的空间环境很重要。
• Monoesters of glycosides and a process for enzymatic preparation thereof
  申请人：Novo Nordisk A/S

  公开号：US05191071A1

  公开（公告）日：1993-03-02

  Compounds of the formula (R-COO).sub.n X-OR.sup.1, wherein R.sup.1 is optionally substituted alkyl, phenyl, or alkyl phenyl, n is 1, 2 or 3, X is a carbohydrate moiety, and R is optionally substituted alkyl, have superior effects as additives in detergents. These compounds can be prepared by esterification of glycosides using specific enzymes.

  式为(R-COO).sub.n X-OR.sup.1的化合物，其中R.sup.1是可选择取代的烷基、苯基或烷基苯基，n为1、2或3，X是碳水化合物基团，R是可选择取代的烷基，作为洗涤剂添加剂具有卓越效果。这些化合物可以通过使用特定酶对糖苷进行酯化来制备。
• Protection-free Synthesis of Alkyl Glycosides under Hydrogenolytic Conditions
  作者：Masaki Ishihara、Yuka Takagi、Gefei Li、Masato Noguchi、Shin-ichiro Shoda

  DOI：10.1246/cl.130646

  日期：2013.10.5

  A convenient protection-free synthetic route for the preparation of alkyl glycosides has been developed. The alcoholysis of one-step preparable glycosyl donors, 4,6-dibenzyloxy-1,3,5-triazin-2-yl (DBT) glycosides, under hydrogenolytic conditions gave the corresponding glycosides in good yields without the addition of any acid promoters. The method could be successfully applied to the glycosylation of an acid-labile oligosaccharide.

  已开发出一种方便的无保护合成路线用于烷基糖苷的制备。在氢解条件下，一步可制备的糖苷供体4,6-二苯氧基-1,3,5-三嗪-2-基(DBT)糖苷的醇解反应，能够在不添加任何酸催化剂的情况下，以良好的产率得到相应的糖苷。该方法可以成功应用于酸不稳定的寡糖的糖基化。
• 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...
• ENZYME-DIRECTED IMMUNOSTIMULANT AND USES THEREOF CROSS-REFERENCE TO RELATED APPLICATION(S)
  申请人：Washington State University

  公开号：US20180094015A1

  公开（公告）日：2018-04-05

  The disclosed invention relates to the novel composition of matter that allows for the controlled release of highly active compounds to be delivered to a desired site. This novel composition utilizes the immune system to allow for the controlled release of desired compounds. The present invention can utilize a plurality of highly active compounds, with one embodiment being the use of chemotherapeutics for the treatment of cancer.

  所披露的发明涉及一种新型物质组合，该组合允许高活性化合物的受控释放以传递到所需的部位。这种新型组合利用免疫系统，以实现所需化合物的受控释放。本发明可以利用多种高活性化合物，其中一种实施方式是使用化疗药物治疗癌症。