1-O-methyl 3,5-di-O-benzyl α(D)xylo-pentoaldofuranose | 79083-38-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-methyl 3,5-di-O-benzyl α(D)xylo-pentoaldofuranose
• 英文别名: methyl 3,5-di-O-benzyl-α-D-xylofuranoside；methyl-3,5-di-O-benzyl-α-D-xylofuranose；1-O-methyl-3,5-di-O-benzyl-α-D-xylofuranose；(2S,3R,4R,5R)-2-methoxy-4-phenylmethoxy-5-(phenylmethoxymethyl)oxolan-3-ol
• CAS: 79083-38-8
• 化学式: C₂₀H₂₄O₅
• 分子量: 344.408
• InChiKey: SOWIHMANTOCUNZ-ZRNYENFQSA-N

物化性质

• 沸点：
  497.0±45.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-O-methyl 3,5-di-O-benzyl α(D)xylo-pentoaldofuranose 在 钯 咪唑 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 四丁基氟化铵 、 silica gel 、 sodium hydride 、 对甲苯磺酸 、 溶剂黄146 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 甲醇 、 甲酸 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-hexanoyl-3-[(4R,5R)-5-(methoxymethoxy)-2-phenyl-1,3-dioxan-4-yl]-2H-furan-5-one
  参考文献：
  名称：

  Formal Synthesis of (-)-Syringolide 1 Starting from D-Xylose Based on a Biomimetic Strategy

  摘要：

  An expeditious and practical synthertic process for a nonproteinaceous elicitor, (-)-syringolide 1, has been developed in a short number of steps utilizing the putative biosynthetic pathway by featuring the elaboration of the protected D-xylose as a starting material.

  DOI：

  10.3987/com-97-7926
• 作为产物：
  描述：

  1,2:3,5-双-O-异亚丙基-alpha-D-呋喃木糖 在 氢氧化钾 、 硫酸 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 55.0h， 生成 1-O-methyl 3,5-di-O-benzyl α(D)xylo-pentoaldofuranose
  参考文献：
  名称：

  Aminonuclosides and Their Derivatives; XII¹. A New Synthesis of 1-O-Methyl-3-azido-2,3-dideoxy-D-ribofuranose

  摘要：

  DOI：

  10.1055/s-1984-31038

文献信息

• A convenient method for deuteration at the alpha position of an oxo group in carbohydrates
  作者：Ahmed El Nemr、Tsutomu Tsuchiya

  DOI：10.1016/s0040-4039(98)00539-5

  日期：1998.5

  CH-Hydrogens at the alpha position of an oxo group in carbohydrates are readily exchanged in 4:4:2:3 1,4-dioxane-THF-Et3N-D2O.

  碳水化合物中一个羰基的α位上的CH-氢很容易在4：4：2：3 1,4-二恶烷-THF-Et 3 N-D 2 O中交换。
• Synthesis of Guanidines From Azides: A General and Straightforward Methodology In Carbohydrate Chemistry
  作者：Andrés G. Santana、Cosme G. Francisco、Ernesto Suárez、Concepción C. González

  DOI：10.1021/jo100876r

  日期：2010.8.6

  The ability of the guanidinylating reagent N′,N′′-diBoc-N-triflyl-guanidine (GN-Tf) to react with in situ formed free amines from azides in carbohydrate scaffolds was explored. This reaction proved to be an efficient method to prepare guanidine derivatives in a one-pot manner with good to excellent yields, either with primary or secondary azides with different substitution patterns. Labile protecting

  所述guanidinylating试剂的能力Ñ '，Ñ ''-diBoc- ñ -triflyl胍（GN-TF）与原位形成的游离胺在碳水化合物支架叠氮化物反应进行了探讨。该反应被证明是一种有效的方法，以一锅法方式制备具有良好或优异产率的胍衍生物，可以使用具有不同取代方式的伯或仲叠氮化物。在这些氢解条件下不除去不稳定的保护基，例如苄基醚。
• The Use of Grignard Reagents in the Synthesis of Carbohydrates. III. The One-way Anomerization of Methyl Glycofuranosides and the Opening of Their Furanose Rings
  作者：Masajiro Kawana、Hiroyoshi Kuzuhara、Sakae Emoto

  DOI：10.1246/bcsj.54.1492

  日期：1981.5

  The anomerization of methyl glycofuranoside derivatives with methylmagnesium iodide or t-butylmagnesium bromide occurred in a one-way manner. For example, methyl 5-O-benzyl-β-D-ribofuranoside (3β) was converted into the corresponding α-anomer (3α) in a 95% yield when a mixture of 3β and t-butylmagnesium bromide in benzene–ether was heated at about 75 °C to remove the ether; the reverse reaction (from

  甲基呋喃糖苷衍生物与甲基碘化镁或叔丁基溴化镁的异构化以单向方式发生。例如，当 3β 和叔丁基溴化镁在苯-醚中的混合物加热时，甲基 5-O-苄基-β-D-呋喃核糖苷 (3β) 以 95% 的产率转化为相应的 α-异头物 (3α)在约 75°C 下除去乙醚；逆反应（从3α到（3β）没有进行。3β与甲基碘化镁反应得到开链产物（33%），除3α（30%）外，还测试了20种异头异构体，并对其作用机理进行了研究。在反应过程中也观察到用格氏试剂裂解苄基或三苯甲基保护基团。
• Synthesis, Conformational Analysis and Biological Studies of Cyclic Cationic Antimicrobial Peptides Containing Sugar Amino Acids
  作者：Tushar Kanti Chakraborty、Dipankar Koley、Rapolu Ravi、Viswanatha Krishnakumari、Ramakrishnan Nagaraj、Ajit Chand Kunwar

  DOI：10.1021/jo801123q

  日期：2008.11.21

  Sugar amino acid based 24-membered macrocyclic C2-symmetric cationic peptides were designed and synthesized. The cationic group was introduced in the sugar amino acids. The conformation of these cyclic compounds was ascertained through NMR techniques, which proved they were amphipathic in nature. All the compounds were bacteriolytic, showed good activity against the Gr(+ve) and Gr(-ve) bacteria, and

  设计并合成了基于糖氨基酸的24元大环C2对称阳离子肽。阳离子基团被引入糖氨基酸中。这些环化合物的构象通过NMR技术确定，证明它们本质上是两亲的。所有化合物均具有溶菌作用，对Gr（+ ve）和Gr（-ve）细菌表现出良好的活性，并且溶血活性低。
• 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.