methyl 2,3-anhydro-5-O-benzyl-α-D-ribofuranoside | 20187-72-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2,3-anhydro-5-O-benzyl-α-D-ribofuranoside
• 英文别名: (1R,2S,4R,5R)-2-methoxy-4-(phenylmethoxymethyl)-3,6-dioxabicyclo[3.1.0]hexane
• CAS: 20187-72-8
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: XAOAXRUYUGVVRU-LPWJVIDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  40.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2,3-anhydro-5-O-benzyl-α-D-ribofuranoside 在 三氟化硼乙醚 作用下， 以 甲醇 为溶剂， 以78%的产率得到2,3-Anhydro-5-O-benzyl-β-D-ribofuranoside de methyle
  参考文献：
  名称：

  FK-506的全合成。第1部分：C16–C34片段的构建

  摘要：

  C23–C27 1,3-二醇是通过Brown的crotylation-osmylation或区域和D-xylofuranose衍生的2,3-anhydro-β-rifurfuranoside的立体选择性开口而构建的。路易斯酸用受保护的硫代糠醛醇催化环氧化物开环，然后氧化螺环缩酮化，将C21–C24螺缩酮建立为掩蔽的α'-烯丙基醛醇。C19-C20三取代的烯烃是通过锆催化的碳铝化反应合成的-用较高级的铜酸盐原位进行金属转移，然后将立体选择性的共轭物加成螺碳烯酮。C27-C28三取代烯烃是通过将铜酸甲酯与烯醇三酯偶联（通过声波作用）或通过C17-醛与C28-乙烯基溴化镁之间的直接偶联而形成的。

  DOI：

  10.1016/s0040-4020(97)00865-x
• 作为产物：
  描述：

  在 potassium hydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 以37%的产率得到Methyl 2,3-anhydro-5-O-benzyl-α-D-lyxofuranoside
  参考文献：
  名称：

  Methyl-α-d-2-selenonyl Pent-2-enofuranoside: A Reactive Selenosugar for the Diversity Oriented Synthesis of Enantiomerically Pure Heterocycles, Carbocycles, and Isonucleosides

  摘要：

  The construction of vinyl selenone on a furanoside led to a highly reactive synthetic intermediate methyl-alpha-D-2-selenonyl pent-2-enofuranoside composed of a masked aldehyde, an electron-deficient double bond along with an excellent leaving group. This new Michael acceptor on reactions with different nudeophiles afforded bicyclic azasugars, cydopropanated carbohydrate, dihydrofuran- and dihydroisoxazole- substituted furanosides, and isonudeosides in moderate to good yields. Hydrolysis of the hemiacetal linkage of some of these modified carbohydrates afforded enantiopure aziridines, nitrocydopropane, and dihydrofuran.

  DOI：

  10.1021/acs.joc.5b01192

文献信息

• A Diastereoselective Unique Route to Cyclopropanes Functionalized at All Three Ring Carbon Atoms from Acyclic Vinyl Sulfone-Modified Carbohydrates
  作者：Ananta Kumar Atta、Tanmaya Pathak

  DOI：10.1021/jo802709q

  日期：2009.4.3

  In a departure from the current trend of using metal-catalyzed routes to cyclopropanation, pentosyl and hexosyl vinyl sulfone-modified carbohydrates having the terminal double bond and a suitably positioned leaving group are reacted in a stereoselective fashion with a series of nucleophiles to yield a myriad of cyclopropanes substituted at all three ring carbon atoms.

  与当前使用金属催化途径进行环丙烷化的趋势背道而驰，具有末端双键和适当位置的离去基团的戊糖基和己糖基乙烯基砜改性的碳水化合物与一系列亲核试剂以立体选择性方式反应，生成无数种在全部三个环碳原子上取代的环丙烷的数目。
• 一种氟代糖内酯合成方法
  申请人：江西师范大学

  公开号：CN114213366A

  公开（公告）日：2022-03-22

  本发明公开了一种氟代糖内酯合成方法。该方法以D‑木糖为起始原料，通过对羟基进行保护合成缩水内醚糖化合物中间体，再经过糖环醇的立体转化、上苄基、脱甲苷、氧化羟基等步骤，即得氟代糖内酯；该合成方法采用的原料简单、廉价易得，且每一个合成步骤都条件温和，处理过程简单，收率相对较高，为含氟生物活性分子的设计提供新的原料和合成途径。
• Regioselective Introduction of 2-Propynyl Groups into the C-2 or C-3 Position of Furanoside Ring
  作者：Dai Kubota、Oyo Mitsunobu

  DOI：10.1246/cl.1997.517

  日期：1997.6

  The reaction of methyl 2,3-anhydro-α-D-ribofuranoside or methyl 2,3-anhydro-5,6-O-cyclohexylidene-α-D-allofuranoside with 2-propynyl metallic reagents exclusively gave the corresponding 2-C-(2-propynyl)-arabino-pentofuranosides and 2-C-(2-propynyl)-altro-hexofuranosides, respectively. In contrast, the β-anomers were selectively attacked at the position 3 to afford the corresponding 3-C-(2-propynyl)furanosides

  甲基 2,3-脱水-α-D-呋喃核糖苷或甲基 2,3-脱水-5,6-O-亚环己基-α-D-异呋喃糖苷与 2-丙炔基金属试剂反应完全得到相应的 2-C- (2-propynyl)-arabino-pentofuranosides 和 2-C-(2-propynyl)-altro-hexofuranosides 分别。相比之下，β-端基异构体在位置 3 处被选择性攻击以提供相应的 3-C-(2-丙炔基)呋喃糖苷。
• Enantiopure 1,4,5-Trisubstituted 1,2,3-Triazoles from Carbohydrates: Applications of Organoselenium Chemistry
  作者：Atanu Bhaumik、Supravat Samanta、Tanmaya Pathak

  DOI：10.1021/jo5009564

  日期：2014.8.1

  A wide range of stable vinyl selenone-modified furanosides has been synthesized for the first time. These 2 pi-partners undergo 1,3-dipolar cycloaddition reactions with a wide range of organic azides to afford enantiopure trisubstituted triazoles. Furanosyl rings opened up during triazole synthesis to generate polyfunctionalized molecules, ready to undergo further transformations. This strategy is one of the most convenient methods for the synthesis of enantiopure 1,4,5-trisubstituted 1,2,3-triazoles where the chiral components are attached to C-4 or C-5 position of triazole ring. These triazoles are formed in a regioselective manner, and several pairs of regioisomeric triazoles have also been synthesized. The approach affords densely functionalized triazoles, which are amenable to further modifications because of the presence of aldehyde and hydroxyl groups. This powerful and practical route adds to the arsenals of chemists and biologists interested in the synthesis and applications of triazoles.
• Fluorination by anchimeric assistance of a diallylamino group: application to the synthesis of some methyl aminofluoropentofuranosides
  作者：Marie-Béatrice Giudicelli、Marie-Agnès Thomé、Dominique Picq、Daniel Anker

  DOI：10.1016/0008-6215(93)84057-d

  日期：1993.10

  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.