methyl L-ribofuranoside | 162491-62-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl L-ribofuranoside
• 英文别名: 1-O-Methyl-L-ribofuranose；(2S,3R,4S)-2-(hydroxymethyl)-5-methoxyoxolane-3,4-diol
• CAS: 162491-62-5
• 化学式: C₆H₁₂O₅
• 分子量: 164.158
• InChiKey: NALRCAPFICWVAQ-NNXAEHONSA-N

物化性质

• 沸点：
  348.7±42.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  11
• 可旋转键数：
  2
• 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：

  methyl L-ribofuranoside 在 三氟甲磺酸 、 硫酸 、 lithium carbonate 作用下， 以 乙酸甲酯 为溶剂， 20.0~115.0 ℃ 、3.0 kPa 条件下， 反应 13.5h， 生成 methyl 1-(2,3,5-tri-O-acetyl-β-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate
  参考文献：
  名称：

  Synthesis of Methyl 1-(2,3,5-Tri-O-acetyl-β-l-ribofuranosyl)-1,2,4- triazole-3-carboxylate from l-Ribose:  From a Laboratory Procedure to a Manufacturing Process

  摘要：

  A two-step manufacturing process for methyl 1-(2,3,5-tri-O-acetyl-beta-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate (1) was developed. In step 1, L-ribose was converted to a beta/alpha mixture of 1,2,3,5-tetra-O-acetyl-L-ribofuranoses (2 and 4). The step contained four chemical transformations and was completed in "one-pot" in approximately 95% yield. The crude step 1 product was reacted with methyl 1,2,4-triazole-3-carboxylate (3) in step 2 to produce 1. The successful utilization of both isomers (2 and 4) in step 2 offered advantages of higher overall yield and a much simplified process by eliminating the isolation of pure 2. The process was successfully scaled up to the pilot plant and subsequently in a manufacturing campaign using commercial production facilities.

  DOI：

  10.1021/op050051m
• 作为产物：
  描述：

  5-O-三苯甲基-D-呋喃核糖 在 sodium tetrahydroborate 、 甲酸 、 硫酸 、 potassium carbonate 、 三乙胺 、 三氟乙酸酐 作用下， 以 吡啶 、 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 2.12h， 生成 methyl L-ribofuranoside
  参考文献：
  名称：

  Synthesis and Testing of New Modified Nucleosides

  摘要：

  New efficient routes for the high-yielding synthesis of several classes of modified nucleosides have been developed. We have prepared both the D- and L-enantiomers of the methylene-expanded oxetanocin isonucleosides 1a-e and the L-2',3'-dideoxy isonucleosides 2abc (both the oxa and thia analgoues) as well as new routes for the preparation of L-ribose and 2-deoxy L-ribose 3ab and their modified nucleosides 4.

  DOI：

  10.1080/15257779908041490

文献信息

• Total Chemical Synthesis and Folding of All-<scp>l</scp> and All-<scp>d</scp> Variants of Oncogenic KRas(G12V)
  作者：Adam M. Levinson、John H. McGee、Andrew G. Roberts、Gardner S. Creech、Ting Wang、Michael T. Peterson、Ronald C. Hendrickson、Gregory L. Verdine、Samuel J. Danishefsky

  DOI：10.1021/jacs.7b02988

  日期：2017.6.7

  of hydrophobic binding pockets. Herein, we report a total chemical synthesis of all-l- and all-d-amino acid biotinylated variants of oncogenic mutant KRas(G12V). The protein is synthesized using Fmoc-based solid-phase peptide synthesis and assembled using combined native chemical ligation and isonitrile-mediated activation strategies. We demonstrate that both KRas(G12V) enantiomers can successfully

  Ras 蛋白是参与细胞增殖和存活调节的重要 GTP 酶。Ras 的突变致癌形式会改变效应子结合和先天 GTP 酶活性，导致下游信号转导失调。Ras 的突变形式与大约 30% 的人类癌症有关。尽管数十年来一直致力于开发直接 Ras 抑制剂，但 Ras 长期以来一直被认为是“不可成药的”，因为它对 GTP 具有高亲和力并且缺乏疏水性结合袋。在此，我们报告了致癌突变体 KRas(G12V) 的全 L-和全 D-氨基酸生物素化变体的全化学合成。该蛋白质使用基于 Fmoc 的固相肽合成法合成，并使用组合的天然化学连接和异腈介导的激活策略进行组装。我们证明两种 KRas(G12V) 对映体都可以成功折叠并结合核苷酸底物和结合配偶体，并具有可观察到的对映体歧视。通过证明镜像形式的 KRas 与其相应的对映体三磷酸核苷酸结合的功能能力，本研究为利用该材料进行进一步的生化研究奠定了基础。特别是，这种蛋白质将使镜像酵母表面展示实验能够识别致癌
• 2'-deoxy-L-nucleosides
  申请人：Watanabe Kyoichi

  公开号：US20050090660A1

  公开（公告）日：2005-04-28

  This invention provides processes for the preparation of compounds having the structure: wherein X and Y are same or different, and H, OH, OR, SH, SR, NH 2 , NHR′, or NR′R″ Z is H, F, Cl, Br, I, CN, or NH 2 . R is hydrogen, halogen, lower alkyl of C 1 -C 6 or aralkyl, NO 2 , NH 2 , NHR′, NR′R″, OH, OR, SH, SR, CN, CONH 2 , CSNH 2 , CO 2 H, CO 2 R′, CH 2 CO 2 H, CH 2 CO 2 R′, CH═CHR, CH 2 CH═CHR, or C═CR. R′ and R″ are same or different, and lower alkyl of C 1 -C 6 . R 13 is hydrogen, alkyl, acyl, phosphate (monophosphate, diphosphate, triphosphate, or stabilized phosphate) or silyl; and

  这项发明提供了制备具有以下结构的化合物的方法： 其中 X和Y相同或不同，且H、OH、OR、SH、SR、NH2、NHR′或NR′R″ Z为H、F、Cl、Br、I、CN或NH2 R为氢、卤素、C1-C6的低碳烷基或芳基烷基、NO2、NH2、NHR′、NR′R″、OH、OR、SH、SR、CN、CONH2、CSNH2、CO2H、CO2R′、CH2CO2H、CH2CO2R′、CH═CHR、CH2CH═CHR或C═CR。 R′和R″相同或不同，且为C1-C6的低碳烷基。 R13为氢、烷基、酰基、磷酸酯（单磷酸酯、二磷酸酯、三磷酸酯或稳定磷酸酯）或硅基。
• METHOD FOR PRODUCING THIOLANE SKELETON-TYPE GLYCOCONJUGATE, AND THIOLANE SKELETON-TYPE GLYCOCONJUGATE
  申请人：FUJIFILM Corporation

  公开号：US20160355536A1

  公开（公告）日：2016-12-08

  There is provided a production method of a compound represented by the following formula (II) through a step of reacting a compound represented by the following General Formula (I) with a sulfur compound. In General Formulas (I) and (II), R 1 represents a hydrogen atom or an acyl group, R 2 represents a hydrogen atom, a fluorine atom, an acyloxy group, an arylmethyloxy group, an allyloxy group, an arylmethyloxycarbonyloxy group, or an allyloxycarbonyloxy group, R 3 represents a hydrogen atom or an acyloxy group, R 5 represents an alkyl group or an aryl group, and X represents a leaving group. Here, in a case where R 2 is a fluorine atom, an acyloxy group, an arylmethyloxy group, an allyloxy group, an arylmethyloxycarbonyloxy group, or an allyloxycarbonyloxy group, R 3 is an acyloxy group.

  提供了一种通过将通用式（I）表示的化合物与硫化合物反应的步骤来制备通式（II）表示的化合物的生产方法。在通式（I）和（II）中，R1代表氢原子或酰基，R2代表氢原子、氟原子、酰氧基、芳基甲氧基、烯丙氧基、芳基甲氧羰氧基或烯丙氧羰氧基，R3代表氢原子或酰氧基，R5代表烷基或芳基，X代表离去基团。在R2为氟原子、酰氧基、芳基甲氧基、烯丙氧基、芳基甲氧羰氧基或烯丙氧羰氧基的情况下，R3为酰氧基。
• Process for producing a ribofuranose
  申请人：——

  公开号：US20040034213A1

  公开（公告）日：2004-02-19

  A method of converting pure &agr;-anomer or &bgr;/&agr;-anomer mixtures of 1,2,3,5-tetra-O-acetyl-L-ribofuranose to methyl-1-(2,3,5 -tri-O-acetyl-&bgr;-L-ribofuranosyl)-1,2,4-triazole-3-carboxylate an intermediate for levovirin, as well as, the novel pure &agr;-anomer, alpha 1,2,3,5-tetra-O-acetyl-L-ribofuiranose, are useful in manufacturing levovirin.

  一种将纯的α-异构体或1,2,3,5-四-O-乙酰-L-核糖呋喃糖的β/α-异构体混合物转化为甲基-1-(2,3,5-三-O-乙酰-β-L-核糖呋喃糖基)-1,2,4-三唑-3-羧酸酯的方法，这是左环病毒素的中间体，以及新颖的纯α-异构体，α-1,2,3,5-四-O-乙酰-L-核糖呋喃糖，对于制造左环病毒素很有用。
• A solid-phase approach to novel purine and nucleoside analogs
  作者：Junbiao Chang、Chunhong Dong、Xiaohe Guo、Weidong Hu、Senxiang Cheng、Qiang Wang、Rongfeng Chen

  DOI：10.1016/j.bmc.2005.05.007

  日期：2005.8

  This paper describes a method for the preparation of purine analogs using the solid-phase approach. Nucleoside bases were constructed on Merrifield resin by sequential displacement of purine dichloride with amines, and after detachment, the purine analogs were condensed with d,l-ribofuranoside compounds by the Vorbruggen method. Thereof, l-ribofuranoside was prepared from l-arabinose via the selective

  本文介绍了一种使用固相方法制备嘌呤类似物的方法。通过用胺依次置换二氯化嘌呤，在Merrifield树脂上构建核苷碱基，分离后，通过Vorbruggen方法将嘌呤类似物与d，l-核呋喃糖苷化合物缩合。其中，通过2-OH基团的选择性氧化还原程序，由1-阿拉伯糖制备1-核呋喃糖苷。一些化合物对PBM细胞中的HIV-1表现出中等活性。