benzyl α-D-arabinofuranoside | 64609-17-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl α-D-arabinofuranoside
• 英文别名: benzyl-α-D-arabinofuranoside；(2R,3S,4S,5S)-2-(hydroxymethyl)-5-phenylmethoxyoxolane-3,4-diol
• CAS: 64609-17-2
• 化学式: C₁₂H₁₆O₅
• 分子量: 240.256
• InChiKey: MBBBSHXQRFAIPA-WYUUTHIRSA-N

物化性质

• 沸点：
  444.6±45.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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-arabinofuranoside 生成 [(2R,3S,4S,5S)-3,4-dihydroxy-5-phenylmethoxyoxolan-2-yl]methyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  WESSEL, HANS PETER, J. CARBOHYDR. CHEM., 7,(1988) N 1, 263-269

  摘要：

  DOI：
• 作为产物：
  描述：

  benzyl 2,3,5-tri-O-benzoyl-α-D-arabinofuranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以2.02 g的产率得到benzyl α-D-arabinofuranoside
  参考文献：
  名称：

  Synthesis of Sulfonium Sulfate Analogues of Disaccharides and Their Conversion to Chain-Extended Homologues of Salacinol: New Glycosidase Inhibitors

  摘要：

  [graphics]Four chain extended homologues of salacinol, a naturally occurring glycosidase inhibitor, were prepared for evaluation as inhibitors of glucosidase enzymes involved in the breakdown of carbohydrates. The syntheses involved the reactions of 1,4-anhydro-2,3,5-tri-O-benzyl-4-thiO-D-arabinitol with cyclic sulfate derivatives of different monosaccharides. Debenzylation of the products afforded the novel sulfonium sulfate derivatives Of D-glucose, D-galactose, D-arabinose, and D-Xylose that are of interest in their own right as glycosidase inhibitors. Reduction to the corresponding alditols then afforded the homologues of salacinol containing polyhydroxylated, acyclic chains of 5- and 6-carbons, differing in stereochemistry at the stereogenic centers. Three of the chain-extended homologues inhibited recombinant human maltase glucoamylase, one of the key intestinal enzymes involved in the breakdown of glucose oligosaccharides in the sinall intestine, with K-i values in the low microinolar range, of approximately the saine inagnitude as salacinol, thus providing lead candidates for the treatment of Type 2 diabetes.

  DOI：

  10.1021/jo052252u

文献信息

• An unexpected rearrangement of pent-4-enofuranosides to cyclopentanones upon hydrogenolysis of the anomeric benzyl group
  作者：Shenyou Nie、Xiaoping Chen、Yuyong Ma、Wei Li、Biao Yu

  DOI：10.1016/j.carres.2016.06.006

  日期：2016.9

  synthesis toward the unique nucleoside antibiotic A201A, we were surprised to find that a benzyl arabino-pent-4-enofuranoside underwent a Ferrier II-like rearrangement readily to provide the corresponding cyclopentanone derivative in high yield and stereoselectivity upon hydrogenolysis of the anomeric benzyl group.

  在合成独特的核苷抗生素A201A的过程中，我们惊讶地发现，苄基阿拉伯戊五-4-烯呋喃糖苷经历了Ferrier II样重排，可在异丁烯基氢解后以高收率和立体选择性提供相应的环戊酮衍生物。团体。
• A Simple Synthesis of C-8 Modified 2-Keto-3-deoxy-d-manno-octulosonic Acid (KDO) Derivatives
  作者：Milton Kiefel、Renee Winzar、Jessica Philips

  DOI：10.1055/s-0029-1219356

  日期：2010.3

  This paper describes a simple and efficient method with which to prepare C-8 modified 2-keto-3-deoxy-d-manno-octulosonic acid (KDO) derivatives from C-5 modified arabinose derivatives.

  本文描述了一种简单高效的方法，可以从C-5修饰的阿拉伯糖衍生物制备C-8修饰的2-酮-3-脱氧-d-甘露-壬酸（KDO）衍生物。
• Glycosidase inhibitors and methods of synthesizing same
  申请人：Pinto Mario Brian

  公开号：US20050065139A1

  公开（公告）日：2005-03-24

  A method for synthesizing Salacinol, its stereoisomers, and analogues, homologues and other derivatives thereof potentially useful as glycolsidase inhibitors. The compounds of the invention may have the general formula (I) or (II): The synthetic schemes comprise reacting a cyclic sulfate with a 5-membered ring sugar containing a heteroatom (X). The heteroatom preferably comprises sulfur, selenium, or nitrogen. The cyclic sulfate and ring sugar reagents may be readily prepared from carbohydrate precursors, such as D-glucose, L-glucose, D-xylose and L-xylose. The target compounds are prepared by opening of the cyclic sulfates by nucleophilic attack of the heteroatoms on the 5-membered ring sugars. The resulting heterocyclic compounds have a stable, inner salt structure comprising a heteroatom cation and a sulfate anion. The synthetic schemes yield various stereoisomers of the target compounds in moderate to good yields with limited side-reactions.

  一种合成Salacinol及其立体异构体、类似物、同系物和其他衍生物的方法，可能用作糖苷酶抑制剂。本发明的化合物可能具有一般式(I)或(II)：合成方案包括将环状硫酸酯与含有杂原子(X)的5元环糖反应。杂原子优选包括硫、硒或氮。环状硫酸酯和环糖试剂可以从碳水化合物前体（如D-葡萄糖、L-葡萄糖、D-木糖和L-木糖）中轻松制备。目标化合物是通过杂原子对5元环糖的亲核攻击打开环状硫酸酯来制备的。所得的杂环化合物具有稳定的内盐结构，包括一个杂原子阳离子和一个硫酸酯阴离子。合成方案以中等至良好的产率产生目标化合物的各种立体异构体，副反应有限。
• Synthesis and mycobacterial growth inhibition activities of bivalent and monovalent arabinofuranoside containing alkyl glycosides
  作者：Kottari Naresh、Binod Kumar Bharati、Narayanaswamy Jayaraman、Dipankar Chatterji

  DOI：10.1039/b803409e

  日期：——

  Arabinofuranosides constitute one of the important components of cell wall structures of mycobacteria. With this importance of arabinofuranosides in mind, alkyl glycosides bearing arabinofuranoside trisaccharides were prepared, wherein the sugars were presented either in the monovalent or bivalent forms. Following the synthesis, the monovalent and bivalent alkyl glycosides were tested for their activities in a mycobacterial growth assay. The growth of the mycobacterial strain M. smegmatis was assessed in the presence of the alkyl glycosides and it was realized that the alkyl glycosides acted as inhibitors of the mycobacterial growth. The inhibition of the growth, caused by the above alkyl glycosides, was not observed for the arabinofuranose trisaccharide alone, without the alkyl groups, and for an alkyl glycoside bearing maltose as the sugar component.

  阿拉伯呋喃糖苷是分枝杆菌细胞壁结构的重要组成部分之一。考虑到阿拉伯呋喃糖苷的这种重要性，我们制备了含有阿拉伯呋喃糖苷三糖的烷基糖苷，其中的糖以一价或二价形式存在。合成后，在分枝杆菌生长试验中测试了单价和二价烷基糖苷的活性。在有烷基苷存在的情况下，对霉菌菌株 M. smegmatis 的生长进行了评估，结果发现烷基苷对霉菌的生长起到了抑制作用。上述烷基糖苷对生长的抑制作用，在单独的阿拉伯呋喃糖三糖、不含烷基的阿拉伯呋喃糖三糖和含麦芽糖的烷基糖苷中都没有观察到。
• Antidiabetic alpha-substituted phosphonates
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0354322A2

  公开（公告）日：1990-02-14

  Alpha-substituted phosphonates are disclosed which stimulate the enzyme fructose-1,6-bisphosphatase and inhibit the enzyme 6-phosphofructo-1-kinase, there­by lowering glucose levels in mammals. These alpha-­substituted phosphonates may thus be used to treat hyperglycemia and/or diabetes. Processes for the syn­thesis of the alpha-substituted phosphonates are also disclosed.

  已公开的α-取代膦酸盐可刺激果糖-1,6-二磷酸酶，抑制6-磷酸果糖-1-激酶，从而降低哺乳动物体内的葡萄糖水平。因此，这些α-取代膦酸盐可用于治疗高血糖和/或糖尿病。还公开了合成α-取代膦酸盐的工艺。