3,5-Di-O-benzyl-α-D-xylofuranose | 120693-82-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,5-Di-O-benzyl-α-D-xylofuranose
• 英文别名: 3,5-di-O-benzyl-D-xylofuranose；3,5-di-O-benzyl-D-xylose；(2S,3R,4R,5R)-4-phenylmethoxy-5-(phenylmethoxymethyl)oxolane-2,3-diol
• CAS: 120693-82-5
• 化学式: C₁₉H₂₂O₅
• 分子量: 330.381
• InChiKey: LYHOPDIJCJJVNG-YRXWBPOGSA-N

物化性质

• 沸点：
  499.3±45.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,5-Di-O-benzyl-α-D-xylofuranose 在 吡啶 、 溴 、 barium carbonate 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 生成 3,5-di-O-benzyl-D-Xylono-1,4-lactone-2-O-trifluoromethanesulphonate
  参考文献：
  名称：

  Ring contraction of 2-o-trifluoromethanesulphonates of α-hydroxy-γ-lactones to oxetane carboxylic esters

  摘要：

  DOI：

  10.1016/s0040-4039(00)97734-7
• 作为产物：
  描述：

  1,2-O-异亚丙基-alpha-D-呋喃木糖 在 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 3,5-Di-O-benzyl-α-D-xylofuranose
  参考文献：
  名称：

  Oxetane δ‐Amino Acids: Chemoenzymatic Synthesis of 2,4‐Anhydro‐5‐N‐(t‐butoxycarbonyl)amino‐D‐lyxonic Acid

  摘要：

  Starting from 1,2-O-isopropylidene-D-xylose, methyl 2,4-anhydro-3,5-di-O-benzyl-D-lyxonate ( 4) was synthesized. Debenzylation and transformation of the primary hydroxyl group yielded methyl 2,4-anhydro-5-N-(t-butoxycarbonyl)amino-D-lyxonate (9). While transesterification of 4 under basic reaction conditions was straightforward, an analogous reaction with 9 was not successful. After screening of several lipases, the enzymatic transesterification of 9 was achieved with lipase L2 from Candida antarctica to furnish the title compound 2,4-anhydro-5-N-(t-butoxycarbonyl)amino-D-lyxonic acid in excellent yield. The stereochemistry at the oxetane ring was proven by an x-ray structure of the intermediate methyl 2,4-anhydro-5-azido-D-lyxonate.[GRAPHICS]

  DOI：

  10.1080/07328300600732485

文献信息

• Furanosyl Oxocarbenium Ion Conformational Energy Landscape Maps as a Tool to Study the Glycosylation Stereoselectivity of 2‐Azidofuranoses, 2‐Fluorofuranoses and Methyl Furanosyl Uronates
  作者：Stefan van der Vorm、Thomas Hansen、Erwin R. van Rijssel、Rolf Dekkers、Jerre M. Madern、Herman S. Overkleeft、Dmitri V. Filippov、Gijsbert A. van der Marel、Jeroen D. C. Codée

  DOI：10.1002/chem.201900651

  日期：2019.5.23

  reactive intermediates is dictated by the conformation of these species. The nature and configuration of functional groups on the carbohydrate ring affect the stability of glycosyl oxocarbenium ions and control the overall shape of the cations. We herein map the stereoelectronic substituent effects of the C2‐azide, C2‐fluoride and C4‐carboxylic acid ester on the stability and reactivity of the complete

  糖基氧碳鎓离子的3D形状决定了它们的稳定性和反应性，在这些反应性中间体上发生的S N 1反应的立体化学过程取决于这些物质的构象。碳水化合物环上官能团的性质和构型影响糖基氧碳鎓离子的稳定性，并控制阳离子的整体形状。我们在本文中通过组合计算和实验方法，绘制了C2-叠氮化物，C2-氟化物和C4-羧酸酯的立体电子取代基对整套非对映异构呋喃糖酶的稳定性和反应性的影响。出乎意料的是，所有研究的呋喃糖基供体都以高度立体选择性的方式反应，从而生成1,2-顺式产品，木糖系列反应除外。核糖，阿拉伯糖和lyxo构成的呋喃糖苷的1,2-顺式选择性可以追溯到中间氧碳鎓离子的最低能量3 E或E 3构象异构体。对木糖基供体的选择性缺乏与采用其他构象的氧碳鎓离子的出现有关。
• Study on fluorination-toxicity relationships. Syntheses of 1-N-[(2R,3R)- and (2R,3S)-4-amino-3-fluoro-2-hydroxybutanoyl] derivatives of kanamycins
  作者：Yoshiaki Takahashi、Chiga ueda、Tsutomu Tsuchiya、Yoshihiko Kobayashi

  DOI：10.1016/0008-6215(93)84060-j

  日期：1993.10

  (2R,3R)- And (2R,3S)-4-azido-3-fluoro-2-hydroxybutanoic acids (11 and 22) have been prepared from 3-deoxy-3-fluoro-1,2-0-isopropylidene-a-D-glucofuranose (1) and 3,5-di-O-benzyl-1,2-O-isopropylidene-alpha-D-xylofuranose (12), respectively. They were then coupled to the H2N-1 group of suitably protected kanamycin A or kanamycin B analogs to give, 1-N-[(2R,3R)- and (2R,3S)-4-amino-3-fluoro-2-hydroxybutanoyl]kanamycins (32-35). This group of compounds (32-34) exhibited similar antibacterial activity and toxicity level as those of the corresponding 1-N-[(S)-4-amino-2-hydroxybutanoyl] (AHB) derivatives of kanamycins. The base strength of the H2N-4''' group of 32 and 34, as determined by C-13 NMR spectroscopy (in D2O) at varying pD values, was found to be lower when compared to the basicity for the corresponding AHB analogs. The relationship between observed toxicity and base strength of the H2N-4''' group is discussed.

  (2R,3R)-和(2R,3S)-4-叠氮-3-氟-2-羟基丁酸(11和22)分别由3-去氧-3-氟-1,2-O-异丙叉基-a-D-古洛吡喃糖(1)和3,5-二-O-苯甲基-1,2-O-异丙叉基-a-D-木糖吡喃糖(12)制备。随后，它们被连接到适当保护的卡那霉素A或卡那霉素B类似物的H2N-1基团上，生成1-N-[(2R,3R)-和(2R,3S)-4-氨基-3-氟-2-羟基丁酰]卡那霉素(32-35)。该类化合物(32-34)表现出与卡那霉素对应1-N-[(S)-4-氨基-2-羟基丁酰](AHB)衍生物相似的抗菌活性和毒性水平。通过C-13核磁共振光谱(在D2O中，不同pD值测定)， -4'''基团(32和34)的碱性强弱与对应的AHB类似物相比较低。观察到的毒性和 -4'''基团的碱强度之间的关系进行了讨论。
• 1,2-Cyclic sulfite and sulfate furanoside diesters: improved syntheses and stability
  作者：Christopher Hardacre、Ivano Messina、Marie E. Migaud、Kerry A. Ness、Sarah E. Norman

  DOI：10.1016/j.tet.2009.06.013

  日期：2009.8

  The facile syntheses of 1,2- and 3,5-cyclic sulfite and sulfate furanoside diesters were conducted in molecular solvents and ionic liquids in the presence of immobilised morpholine. Molecular solvents and ionic liquids performed similarly with regards to overall yields. However, the use of ILs allowed for the reactions to be carried out under atmospheric conditions and showed good recyclability. Additionally

  在固定的吗啉存在下，在分子溶剂和离子液体中轻松合成1,2-和3,5-环亚硫酸盐和硫酸呋喃糖苷二酯。就总产率而言，分子溶剂和离子液体的表现相似。然而，使用IL允许反应在大气条件下进行并且显示出良好的可回收性。另外，IL中的有机物，特别是双（三氟甲磺酰基）酰亚胺}和三五氟乙基三氟磷酸酯基离子液体，在离子液体中实现了产品稳定性的提高，它们也是控制亚硫酰氯和硫酰氯水解的极好介质。
• Studies towards the synthesis of polyhydroxylated pyrrolidine alkaloids isolated from Broussonetia kazinoki (moraceae)
  作者：Marc E. Bouillon、Robert J. Nash、Stephen G. Pyne

  DOI：10.1016/j.tet.2022.133104

  日期：2022.12

  (−)-(6S)-12′-hydroxydodecylmoranoline are reported. These syntheses start from d-xylose employing the Petasis borono-Mannich reaction to stereoselectively introduce the amino group, followed by a chemo- and regioselective O-mesylation to deliver the fully functionalized pyrrolidine moiety after intramolecular SN2-cyclisation. The synthesis of the latter targeted compound involved a ring expansion process of

  L-AB1、L-DMDP 和新型化合物 (−)-phenethyl-L-AB1、(−)-10′-deoxobroussonetine C、(−)-10′-deoxobroussonetine E、(−)-报道了 1'-epi-10'-deoxobroussonetine E 和 (−)-(6S)-12'-hydroxydodecylmoranoline。这些合成从d -木糖开始，采用 Petasis 硼-曼尼希反应立体选择性地引入氨基，然后进行化学和区域选择性 O-甲磺酰化，在分子内 S N之后传递完全功能化的吡咯烷部分2-环化。后一种目标化合物的合成涉及脯氨醇部分在 Mitsunobu 反应条件下扩环成哌啶衍生物的过程。由于在合成的最后阶段形成了意想不到的四氢呋喃衍生物，因此尝试合成所需的 ent-broussonetine C 未成功。还介绍了四种新目标化合物对一组十种糖苷的糖苷酶抑制活性。
• Novel <scp>d</scp>-Xylose Derivatives Stimulate Muscle Glucose Uptake by Activating AMP-Activated Protein Kinase α
  作者：Arie Gruzman、Ofer Shamni、Moriya Ben Yakir、Daphna Sandovski、Anna Elgart、Evgenia Alpert、Guy Cohen、Amnon Hoffman、Yehoshua Katzhendler、Erol Cerasi、Shlomo Sasson

  DOI：10.1021/jm8008713

  日期：2008.12.25

  Type 2 diabetes mellitus has reached epidemic proportions; therefore, the search for novel antihyperglycemic drugs is intense. We have discovered that D-Xylose increases the rate of glucose transport in a non-insulin-dependent manner in rat and human myotubes in vitro. Due to the unfavorable pharmacokinetic properties Of D-Xylose we aimed at synthesizing active derivatives with improved parameters. Quantitative structure-activity relationship analysis identified critical hydroxyl groups in D-xylose. These data were used to synthesize various hydrophobic derivatives Of D-Xylose of which compound 19 the was most potent compound in stimulating the rate of hexose transport by increasing the abundance of glucose transporter-4 in the plasma membrane of myotubes. This effect resulted from the activation of AMP-activated protein kinase without recruiting the insulin transduction mechanism. These results show that lipophilic D-Xylose derivatives may serve as prototype molecules for the development of novel anti hyperglycemic drugs for the treatment of diabetes.