methyl β-L-arabinofuranoside | 3795-69-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl β-L-arabinofuranoside
• 英文别名: methyl 5-deoxy-β-L-arabino-hexofuranoside；methyl β-L-arabinoside；methyl-L-arabinose；methyl-β-L-arabinofuranoside；Methyl-β-L-arabinofuranosid；(2S,3R,4R,5S)-2-(Hydroxymethyl)-5-methoxytetrahydrofuran-3,4-diol；(2S,3R,4R,5S)-2-(hydroxymethyl)-5-methoxyoxolane-3,4-diol
• CAS: 3795-69-5
• 化学式: C₆H₁₂O₅
• 分子量: 164.158
• InChiKey: NALRCAPFICWVAQ-AZGQCCRYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.93
• 重原子数：
  11.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.15
• 氢给体数：
  3.0
• 氢受体数：
  5.0

安全信息

• 海关编码：
  2932190090

反应信息

• 作为反应物：
  描述：

  methyl β-L-arabinofuranoside 在 三乙基硅烷 、 三氟甲磺酸三甲基硅酯 、 水 作用下， 以 乙腈 为溶剂， 反应 3.0h， 生成 1,4-脱水戊糖醇
  参考文献：
  名称：

  An efficient synthesis of anhydroalditols and allylic-glycosides

  摘要：

  DOI：

  10.1021/jo00381a030
• 作为产物：
  描述：

  L-(+)-arabinose 生成 methyl β-L-arabinofuranoside
  参考文献：
  名称：

  MIZUTANI, KENJI;KASAI, RYOJI;NAKAMURA, MIDORI;TANAKA, OSAMU;MATSUURA, HIR+, CARBOHYDR. RES., 185,(1989) N, C. 27-38

  摘要：

  DOI：

文献信息

• N.m.r. spectral study of α- and β-l-arabinofuranosides
  作者：Kenji Mizutani、Ryoji Kasai、Midori Nakamura、Osamu Tanaka、Hiromichi Matsuura

  DOI：10.1016/0008-6215(89)84018-2

  日期：1989.1

  -arabinofuranosides of various aliphatic alcohols were synthesized and then investigated by n.m.r. spectroscopy. The 13 C-n.m.r. glycosylation shift of these l -arabinofuranosides is very similar to that of l -arabinopyranosides and other glycopyranosides reported previously. The 3 J H-1,H-2 value of these α- l -arabinofuranosides is significantly different from that of the β anomers and can be used

  摘要合成了各种脂肪醇的1-阿拉伯呋喃糖苷的端基异构对，然后通过核磁共振波谱研究。这些1-阿拉伯呋喃糖苷的13 Cn.mr糖基化转变与先前报道的1-阿拉伯吡喃果糖苷和其他糖吡喃糖苷的转变非常相似。这些α-1-阿拉伯呋喃糖苷的3 J H-1，H-2值与β端基异构体的3 J H-1，H-2值显着不同，可用于确定端基构型。然而，与糖吡喃糖苷的情况相反，1-阿拉伯呋喃糖苷的每个异头异构系列的1 J C-1，H-1值彼此非常相似。还通过核磁共振波谱研究了一些含有1-阿拉伯呋喃糖苷单元的二糖。
• Regio- and stereoselective syntheses of l-pentose derivatives from l-arabinose
  作者：Grigorii G. Sivets

  DOI：10.1016/j.tet.2017.12.045

  日期：2018.3

  were accomplished via simple and efficient reduction of methyl 2-O-mesyl-l-arabinofuranoside with L-Selectride or tandem reaction involving a complex hydride 2-deoxygenation/acylation of intermediate 2-deoxysugar. A new synthesis of 2′-deoxy-2′-fluoro-β-l-arabinofuranosyl thymine (l-FMAU) was performed using a mild fluorination of protected l-ribofuranoside and a novel sequence of conversions for

  新颖升-arabinose，升-核糖，2-脱氧-1-核糖和2-氟-2-脱氧升-arabinose衍生物由易于获得的合成升-arabinose。通过1,2-二-O-的区域选择性转化，研究了不同的合成途径，将甲基3,5-二-O-酰化-1-阿拉伯糖（呋喃核糖）呋喃糖苷作为有价值的中间体，用于制备C-2官能化的1-戊糖。乙酰-3,5-二-O-新戊酰-1-呋喃呋喃糖和甲基l的选择性酰化-阿拉伯呋喃糖苷与4-氯苯甲酰或新戊酰氯。甲基2-脱氧-α- 1-核糖呋喃糖苷，其3,5-二-O-酰基衍生物，制备抗病毒2'-脱氧-1-核苷的宝贵前体的简短的三步五步合成法是通过简单的方法完成的和高效率还原的2- ö -mesyl- 1-阿拉伯呋喃糖苷与三仲丁基硼氢化锂或涉及中间体2-脱氧糖的复合氢化物2-脱氧/酰化串联反应。2'-脱氧-2'-氟-β - 1-阿拉伯呋喃糖基胸腺嘧啶（1- FMAU）的新合成是使用受保护
• Preparation of Methyl 2,3-Anhydro- and 2,3-O-Sulfinylfuranosides from Unprotected Furanosides Using the Mitsunobu Reaction
  作者：Oliver Schulze、Jürgen Voss、Gunadi Adiwidjaja

  DOI：10.1055/s-2001-10806

  日期：——

  A new two step procedure for the synthesis of methyl 2,3-anhydro-α-d-lyxofuranoside and methyl 2,3-anhydro-β-d-ribofuranoside from d-xylose involving the intramolecular Mitsunobu reaction is presented. Likewise, methyl 2,3-anhydro-α-l-lyxofuranoside is obtained from l-arabinose. Cyclic sulfites with d-ribo configuration, synthetic equivalents of the corresponding anhydrosugars, are prepared in three steps from d-ribose.

  本研究提出了一种新的两步法，通过分子内 Mitsunobu 反应从 d-xylose 合成甲基 2,3-anhydro-δ-d-lyxofuranoside 和甲基 2,3-anhydro-δ-d-ribofuranoside。同样，从 l-arabinose 中也得到了甲基 2,3-anhydro-δ-l-lyxofuranoside。以 d- 核糖为原料，通过三个步骤制备出具有 d-ribo 构型的环状亚硫酸盐，即相应无水糖的合成等价物。
• Two iridoid glycosides from Rehmannia glutinosa
  作者：Takashi Morota、Hiroshi Sasaki、Hiroaki Nishimura、Kô Sugama、Masao Chin(Chen Zhengxiong)、Hiroshi Mitsuhashi

  DOI：10.1016/s0031-9422(00)97934-2

  日期：1989.1

  Two new iridoid glycosides named jioglutosides A and B, together with 11 known iridoid glycosides, have been isolated from the fresh roots of Rehmannia glutinosa var. hueichingensis. On the basis of chemical and spectral analyses, the structures of jioglutosides A and B have been elucidated.

  两种新的环烯醚萜苷 A 和 B，连同 11 种已知的环烯醚萜苷，已从熟地黄的新鲜根中分离出来。惠清 在化学和光谱分析的基础上，jioglutosides A 和 B 的结构已经阐明。
• Tetrofuranose nucleoside phosphonic acids: Synthesis and properties
  作者：Ivana Poláková、Miloš Buděšínský、Zdeněk Točík、Ivan Rosenberg

  DOI：10.1135/cccc2011038

  日期：——

  New isoelectronic, non-isosteric phosphonate analogues of nucleoside 5′-phosphates featuring the phosphorus moiety directly attached on the sugar ring in the C4′ position are described. The analogues were synthesised by a nucleosidation reaction from tetrofuranosyl phosphonate synthons and silylated nucleobases. The pyrimidine compounds with erythro and threo configuration in both D- and L-series were prepared, and the structures were assigned by NMR spectroscopy. The results of NMR conformational studies show that all calculated conformers have a maximum pucker in the range typical for nucleosides. In all compounds, the S-type conformer is preferred and is more significant in α-D-threo-compounds. Studies on inhibition of thymidine phosphorylase revealed that one of the prepared phosphonic acids was a competitive inhibitor of the enzyme (K_i = 4 μM).

  描述了新的等电子、非同构的磷酸酯类核苷酸5'-磷酸的类似物，其磷酸基直接连接在糖环的C4'位置。这些类似物是通过从四氧杂环磷酸酯合成物和硅化的核碱基进行核苷化反应合成的。制备了具有D-和L-系列中erythro和threo构型的嘧啶化合物，并通过核磁共振谱学确定了它们的结构。核磁共振构象研究的结果显示，所有计算的构象体现出典型的核苷酸范围内的最大皱曲。在所有化合物中，S-型构象体更受青睐，并在α-D-threo-化合物中更为显著。对胸苷磷酸酶抑制的研究表明，所制备的磷酸类化合物之一是该酶的竞争性抑制剂（K_i = 4 μM）。