2,3-anhydro-β-D-ribofuranoside de methyle | 4891-18-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: 2,3-anhydro-β-D-ribofuranoside de methyle
• 英文别名: methyl 2,3-anhydro-β-D-ribofuranoside；methyl-(2,3-anhydro-β-D-ribofuranoside)；Methyl-(2,3-anhydro-β-D-ribofuranosid)；Methyl-<2,3-anhydro-β-D-ribofuranosid>；Methyl 2,3-anhydro-beta-d-ribofuranoside；[(1R,2R,4R,5R)-4-methoxy-3,6-dioxabicyclo[3.1.0]hexan-2-yl]methanol
• CAS: 4891-18-3
• 化学式: C₆H₁₀O₄
• 分子量: 146.143
• InChiKey: JUSRGBNWFOHRCD-KVTDHHQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-anhydro-β-D-ribofuranoside de methyle 在 ammonium hydroxide 作用下， 反应 16.0h， 以100%的产率得到methyl 3-amino-3-deoxy-β-D-xylofuranoside
  参考文献：
  名称：

  Fluorination by anchimeric assistance of a diallylamino group: application to the synthesis of some methyl aminofluoropentofuranosides

  摘要：

  Methyl 2,3-trans-dialkylaminofluoro-alpha(or beta)-D-pentofuranosides were prepared by fluorination wherein the dialkylamino, group assists the replacement of a trans-vicinal mesylate. Whatever the location of the dialkylamino group (alpha or beta face of the ring), the regioselectivity of fluorination depends mainly on the alpha or beta orientation of the anomeric methoxyl group. The use of a diallylamino substituent led to methyl 3-amino-2,3-dideoxy-2-fluoro-beta-D-xylofuranoside, methyl 2-amino-2,3-dideoxy-3-fluoro-alpha-D-arabinofuranoside, methyl 2-amino-2,3-dideoxy-3-fluoro-beta-D-xylofuranoside, and methyl 3-amino-2,3-dideoxy-2-fluoro-alpha-D-arabinofuranoside. Attempts to obtain 2(or 3),5-difluoro analogues staring from corresponding dimesylates gave only disappointing results.

  DOI：

  10.1016/0008-6215(93)84057-d
• 作为产物：
  描述：

  甲基 beta-D-呋喃木糖苷 在 吡啶 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 反应 1.0h， 以71%的产率得到2,3-anhydro-β-D-ribofuranoside de methyle
  参考文献：
  名称：

  Preparation of Methyl 2,3-Anhydro- and 2,3-O-Sulfinylfuranosides from Unprotected Furanosides Using the Mitsunobu Reaction

  摘要：

  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。

  DOI：

  10.1055/s-2001-10806

文献信息

• An efficient synthesis of methyl 2,3-anhydro-α-d-ribofuranoside
  作者：Christopher S. Callam、Rajendrakumar Reddy Gadikota、Todd L. Lowary

  DOI：10.1016/s0008-6215(00)00277-9

  日期：2001.1

  Abstract An efficient synthesis of methyl 2,3-anhydro-α- d -ribofuranoside is reported. Its preparation is achieved via a four-step sequence from methyl 2,3,5-tri-O-benzoyl-α- d -arabinofuranoside in 74% overall yield.

  摘要报道了有效合成2,3-脱水-α-d-核呋喃糖苷甲基的方法。它的制备是通过由4个步骤组成的甲基2,3,5-三-O-苯甲酰基-α-d-阿拉伯呋喃糖苷分四个步骤完成的，总收率为74％。
• A convenient method for the synthesis of cyclic trithiocarbonates on carbohydrate scaffolds
  作者：Muhammad Saeed、Muhammad Abbas、Raid J. Abdel-Jalil、Muhammad Zahid、Wolfgang Voelter

  DOI：10.1016/s0040-4039(02)02529-7

  日期：2003.1

  An efficient regio- and stereoselective method for the synthesis of cyclic trithiocarbonates on carbohydrate skeleton is described. A freshly prepared solution of sodium trithiocarbonate reacts with cis-oriented epoxytriflate pentoses 7–11 to yield the corresponding cyclic trithiocarbonates 12–16. Structures of all new compounds are established through MS, 1H and 13C NMR techniques.

  描述了在碳水化合物骨架上合成环状三硫代碳酸酯的有效的区域选择性和立体选择性方法。钠新鲜制备的溶液发生反应三硫代碳酸酯与顺式取向的epoxytriflate戊糖7 - 11，得到相应的环状三硫代碳酸酯12 - 16。所有新化合物的结构都是通过MS，1 H和13 C NMR技术确定的。
• The thio-Mitsunobu reaction: a useful tool for the preparation of 2,5-anhydro-2-thio- and 3,5-anhydro-3-thiopentofuranosides
  作者：Oliver Schulze、Jürgen Voss、Gunadi Adiwidjaja、Falk Olbrich

  DOI：10.1016/j.carres.2004.04.020

  日期：2004.7

  The unprotected methyl L-arabinofuranosides, D-ribofuranosides and D-xylofuranosides are transformed into the corresponding S-acetyl-5-thio derivatives by the thio-Mitsunobu reaction. Mesylation and subsequent reaction with sodium hydrogen carbonate led, depending on the configuration of the intermediate, to 2,5-anhydro-2-thio- or 3,5-anhydro-3-thiopentofuranosides. Due to inversion at C-3 or C-2 during

  通过硫代-Mitsunobu反应将未保护的甲基L-阿拉伯呋喃糖苷，D-核呋喃糖苷和D-木呋喃糖苷转化为相应的S-乙酰基-5-硫代衍生物。取决于中间体的构型，甲磺酸化和随后与碳酸氢钠的反应导致2，5-脱水-2-硫代-或3，5-脱水-3-硫代呋喃呋喃糖苷。由于在分子内亲核取代过程中在C-3或C-2处发生倒位，所以产物表现出L-lyxo-，D-阿拉伯糖基或D-lyxo-构型。类似地，甲基2,3-脱水-D-呋喃核糖苷生成具有完整2,3-环氧乙烷基团的5-硫代-S-乙酸盐，将其与碳酸氢钠的环氧化物开环和伴随的闭环反应，仅形成3， 5-脱水-3-硫代-D-木呋喃糖苷。相关的3，通过使3，5-二-O-甲酰基-D-阿拉伯呋喃糖苷与硒化氢钠反应，获得5-脱水-3-硒代-D-呋喃呋喃糖苷。多次X射线衍射分析证明了产品的结构。
• Preparation of selenoanhydro- and telluroanhydroglycofuranosides and some corresponding nucleosides
  作者：Gunadi Adiwidjaja、Oliver Schulze、Jürgen Voss、Jörn Wirsching

  DOI：10.1016/s0008-6215(99)00321-3

  日期：2000.4

  methyl 2-telluro-2,5-anhydro-alpha-D-arabinofuranoside. Starting from 5a we prepared 1-(2-seleno-2,5-anhydro-alpha-D-arabinofuranosyl)uracil and the analogous thymidine nucleoside. Compound 6a could not be transformed into nucleosides.

  将甲基2,3-脱水α-D-呋喃呋喃糖苷（3a）转化为2-硒-2,5-脱水α-D-阿拉伯呋喃糖苷甲基（5a）和3-硒-3,5-脱水α-甲基甲酯通过3a的C-5甲磺酸酯，2,3-甲基脱水5 -O-甲磺酰基-α-D-呋喃呋喃糖苷（4a）的C-5甲磺酸酯与硒化氢钠的反应，分两步生成-D-木呋喃糖苷（6a）。相应的3a的β端基异构体产生的甲基3-硒代-3,5-脱水-β-D-木呋喃糖苷为主要产物，仅产生痕量的甲基2-硒代-2,5-脱水-β-D-阿拉伯呋喃糖苷。碲化氢钠将4a转化为甲基2-telluro-2,5-anhydro-alpha-D-arabinofuranoside。从5a开始，我们制备了1-（2-硒基-2，5-脱水-α-D-阿拉伯呋喃糖基）尿嘧啶和类似的胸苷核苷。化合物6a不能转化为核苷。
• Diastereoselective Michael Initiated Ring Closure on Vinyl Sulfone-Modified Carbohydrates:  A Stereospecific and General Route to α-Substituted Cyclopropanes
  作者：Indrajit Das、Tarun K. Pal、Tanmaya Pathak

  DOI：10.1021/jo701378d

  日期：2007.11.1

  Suitably designed vinyl sulfone-modified furanosides act as substrates for Michael initiated ring closure reactions yielding cyclopropanated carbohydrates. The strategy is general in nature and gives access to cyclopropanes with predefined chiralities on three consecutive carbons with varying substitutions at the α-position.

  适当设计的乙烯基砜改性的呋喃糖苷可作为迈克尔引发的闭环反应的底物，产生环丙烷化的碳水化合物。该策略本质上是通用的，并允许在三个连续的碳原子上具有预定义的手性的环丙烷，在α位上具有不同的取代基。