3-O-methyl-D-xylose | 7382-51-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-methyl-D-xylose
• 英文别名: 3-O-methyl-α,β-D-xylopyranose；O³-methyl-D-xylose；O³-methyl-ξ-D-xylopyranose；3-O-methylxylopyranose；(3R,4S,5R)-4-methoxyoxane-2,3,5-triol
• CAS: 7382-51-6
• 化学式: C₆H₁₂O₅
• 分子量: 164.158
• InChiKey: CLSVEGLVXYAUSX-VRPWFDPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  3-O-methyl-D-xylose 、 乙硫醇 在 盐酸 作用下， 以 水 为溶剂， 以76%的产率得到3-O-methyl-D-xylose diethyl dithioacetal
  参考文献：
  名称：

  Novel d-Xylose Derivatives Stimulate Muscle Glucose Uptake by Activating AMP-Activated Protein Kinase α

  摘要：

  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.

  DOI：

  10.1021/jm8008713
• 作为产物：
  描述：

  ((3aR,5R,6S,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-methanol 生成 3-O-methyl-D-xylose
  参考文献：
  名称：

  Novel d-Xylose Derivatives Stimulate Muscle Glucose Uptake by Activating AMP-Activated Protein Kinase α

  摘要：

  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.

  DOI：

  10.1021/jm8008713

文献信息

• Saponin and sapogenol. XXVI. Steroidal saponins from the starfish Acanthaster planci L. (crown of thorns). 2. Structure of the major saponin thornasteroside A.
  作者：ISAO KITAGAWA、MOTOMASA KOBAYASHI

  DOI：10.1248/cpb.26.1864

  日期：——

  The major saponin named thornasteroside A (5) has been isolated from the whole body of starfish Acanthaster planci L. (crown of thorns). In order to facilitate the structural study, thornasteroside A (5) has been converted to a pentaglycoside (designated as dsp-1), which corresponds to a desulfated pregnane-type derivative of 5. On the bases of chemical reactions and physicochemical evidence, the structure of dsp-1 has been elucidated as 10. Based on the accumulated evidence in this and the preceding papers, the structure of thornasteroside A has been established as 20-hydroxy-6α-O-β-D-fucopyranosyl (1→2)-β-D-galactopyranosyl (1→4)-[β-D-quinovopyranosyl (1→2)]-β-D-xylopyranosyl (1→3)-β-D-quinovopyranosyl}-5α-cholest-9 (11)-en-23-on-3β-yl sodium sulfate (5).

  从棘冠海星（Acanthaster planci L.）全身分离得到主要皂苷成分thornasteroside A（5）。为了便于结构研究，将thornasteroside A（5）转化为一种五糖苷（命名为dsp-1），相当于去硫酸化的孕甾烷衍生物。根据化学反应和物化证据，dsp-1的结构被阐明为10。基于本篇及前述论文积累的证据，thornasteroside A的结构被确定为20-羟基-6α-O-β-D-岩藻吡喃糖基（1→2）-β-D-半乳吡喃糖基（1→4）-[β-D-苦苣吡喃糖基（1→2）]-β-D-木吡喃糖基（1→3）-β-D-苦苣吡喃糖基}-5α-胆甾-9（11）-烯-23-酮-3β-基硫酸钠（5）。
• A new steroidal glycoside phrygioside A and its aglycone from the starfish Hippasteria phrygiana
  作者：E. V. Levina、A. I. Kalinovskii、P. V. Andriyashchenko、P. S. Dmitrenok、E. V. Evtushenko、V. A. Stonik

  DOI：10.1007/s11172-005-0165-z

  日期：2004.11

  Three polyhydroxylated steroids were isolated from the Far-Eastern starfish Hippasteria phrygiana collected from the Sea of Okhotsk and were characterized as a new glycoside phrygioside A, viz., sodium (20R, 24S)-3β,4β,7α,8,15β,24-hexahydroxy-24-O-[3-O-methyl-β-D-xylopyranosyl-(1→2)-α-L-arabinofuranosyl]-5α-cholestan-6α-yl sulfate, its aglycone, and the already known marthasterone sulfate.

  从鄂霍次克海采集的远东海星 Hippasteria phrygiana 中分离出三种多羟基化甾体化合物，鉴定为新型糖苷 phrygioside A，即钠 (20R, 24S)-3β,4β,7α,8,15β,24 -hexahydroxy-24-O-[3-O-methyl-β-D-xylopyranosyl-(1→2)-α-L-arabinofuranosyl]-5α-cholestan-6α-yl硫酸盐、它的苷元和已知的marthasterone硫酸盐。
• Pentose derivatives as anti-hyperglycemic drugs
  申请人：Sasson Shlomo

  公开号：US20050277599A1

  公开（公告）日：2005-12-15

  The present invention relates to pentose and pentose derivatives that are effective at increasing glucose transport in a non-insulin dependent manner, and to uses thereof for a) treating and/or preventing hyperglycemia; b) treating and/or preventing the complications of hyperglycemia; c) treating diabetes; d) increasing the rate of cellular glucose transport; e) increasing the rate of cellular glucose uptake; f) improving the ability of a subject to metabolize glucose; g) treating daily blood glucose fluctuations; h) reducing blood sugar levels; i) reducing the dosage of anti-diabetic medication needed for treatment of diabetes. The present invention further provides novel pentose derivatives having beneficial properties in terms of pharmacokinetics, to pharmaceutical compositions comprising these novel compounds and uses thereof.

  本发明涉及以非胰岛素依赖方式有效增加葡萄糖转运的戊糖和戊糖衍生物，并涉及其用于 a) 治疗和/或预防高血糖；b) 治疗和/或预防高血糖并发症；c) 治疗糖尿病；d) 增加细胞葡萄糖转运率； e) 增加细胞葡萄糖摄取率； f) 改善受试者代谢葡萄糖的能力； g) 治疗日常血糖波动； h) 降低血糖水平； i) 减少治疗糖尿病所需的抗糖尿病药物剂量。本发明进一步提供了在药代动力学方面具有有益特性的新型戊糖衍生物，以及包含这些新型化合物的药物组合物及其用途。
• Structure of cucumarioside G1 ? A new triterpene glycoside from the holothurianCucumaria fraudatrix
  作者：Sh. Sh. Afiyatullov、L. Ya. Tishchenko、V. A. Stonik、A. I. Kalinovskii、G. B. Elyakov

  DOI：10.1007/bf00714918

  日期：——
• Glycosides of marine invertebrates. Cucumarioside G1 from the holothurianCucumaria fraudatrix
  作者：Sh. Sh. Afiyatullov、V. A. Stonik、G. B. Elyakov

  DOI：10.1007/bf00576116

  日期：1983.9