甲基 2,3-脱水-beta-D-核吡喃糖苷 | 3150-13-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 甲基 2,3-脱水-beta-D-核吡喃糖苷
• 中文别名: 甲基2,3-脱水-beta-D-核吡喃糖苷
• 英文名称: (1R,2R,5R,6R)-2-Methoxy-3,7-dioxa-bicyclo[4.1.0]heptan-5-ol
• 英文别名: anhydro-2,3-β-D-ribopyranoside de methyle；methyl 2,3-anhydro-β-D-ribopyranoside；methyl 2,3-anhydro-β-L-ribopyranoside；methyl-2,3-anhydro-β-D-ribopyranoside；methyl-(2,3-anhydro-β-D-ribopyranoside)；Methyl-(2,3-anhydro-β-D-ribopyranosid)；Methyl 2,3-anhydro-beta-d-ribopyranoside；(1R,2R,5R,6R)-2-methoxy-3,7-dioxabicyclo[4.1.0]heptan-5-ol
• CAS: 3150-13-8
• 化学式: C₆H₁₀O₄
• 分子量: 146.143
• InChiKey: DISULGQOMPTDEN-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：
  1
• 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

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  甲基 2,3-脱水-beta-D-核吡喃糖苷 在 sodium hydride 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 5.5h， 生成 methyl 3-O-acetyl-4-O-benzyl-β-D-xylopyranoside
  参考文献：
  名称：

  A common access to 2- and 3-substituted methyl β-d-xylopyranosides

  摘要：

  2-Deoxy-, 3-deoxy-, 2-deoxy-2-fluoro- and 3-deoxy-3-fluoro- derivatives of methyl beta -D-xylopyranoside diacetates were prepared by a new common route via 2,3-anhydropentosides. The stereo- and regioselective introduction of fluorine or hydrogen was accomplished by epoxide ring opening of methyl 2,3-anhydro-beta -D-ribopyranoside and methyl 2,3-anhydro-4-O-benzyl-beta -D-lyxopyranoside. Methyl 2.3-anhydro-4-O-benzyl-beta -D-lyxopyranoside was originally obtained in three simple steps from readily available methyl 2,3-anhydro-4-O-benzyl-beta -D-ribopyrinoside. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01957-8
• 作为产物：
  描述：

  methyl-[O2-(toluene-4-sulfonyl)-β-D-arabinopyranoside] 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 34.0h， 生成 甲基 2,3-脱水-beta-D-核吡喃糖苷
  参考文献：
  名称：

  Glycosylation of methyl-2,3-di-O-acetyl-?-D-xylopyranoside triarylmethyl ethers with electron-donor substituents in the aromatic ring by 3,4-di-O-acetyl-1,2-O-[1-(endo-cyano)-ethylidene]-?-D-xylo-pyranose

  摘要：

  DOI：

  10.1007/bf00962335

文献信息

• Construction of the DEF–Benzoxocin Ring System of Nogalamycin and Menogaril via a Reductive Heck Cyclization
  作者：Ruogu Peng、Michael S. VanNieuwenhze

  DOI：10.1021/acs.joc.8b02575

  日期：2019.1.4

  Construction of the DEF-ring system of nogalamycin and menogaril has been achieved with a novel reductive Heck cyclization approach. Our strategy exploited the stereoelectronic preferences dictated by the anomeric effect for introduction of an O-glycosidic bond in order to direct the introduction of a bridging C-glycosidic bond with the desired stereochemistry. Our strategy relied upon a stereoselective

  新颖的还原性Heck环化方法已经实现了诺加霉素和Menogaril的DEF环系统的构建。我们的策略利用了由异头效应所决定的立体电子偏好性，以引入O-糖苷键，从而以所需的立体化学指导C-糖苷键的桥接。我们的策略依赖于立体选择性的O-芳基糖基化反应和高效的亚硒酸酯消除，为研究还原性Heck环化反应提供了关键底物。在优化的条件下，环化反应顺利进行，其收率可与我们先前报道的模型研究中获得的结果相当。
• A total synthesis of (+)-oxybiotin from d-arabinose
  作者：Velimir Popsavin、Goran Benedeković、Mirjana Popsavin、Vladimir Divjaković、Thomas Armbruster

  DOI：10.1016/j.tet.2004.04.040

  日期：2004.6

  A novel ten-step synthesis of (+)-oxybiotin, a biologically active analogue of (+)-biotin, has been achieved starting from d-arabinose.

  从d-阿拉伯糖开始，已经实现了（+）-生物素的生物活性类似物（+）-氧生物素的新颖的十步合成。
• Deoxy and deoxyfluoro analogues of acetylated methyl β-d-xylopyranoside––substrates for acetylxylan esterases
  作者：Mária Mastihubová、Peter Biely

  DOI：10.1016/j.carres.2004.06.001

  日期：2004.8

  synthesized via 2,3-anhydropentopyranoside precursors. Methyl 2,3-anhydro-4-O-benzyl-beta-D-ribopyranoside was transformed into methyl 2,3-anhydro-4-O-benzyl-beta-D-lyxopyranoside in three steps. The epoxide ring opening of 2,3-anhydropentopyranosides was accomplished either by hydride reduction or hydrofluorination. Methyl beta-D-xylopyranoside 2,3,4-tri-O-, 2,4-di-O-, and 3,4-di-O-acetates, and the prepared

  通过2,3合成了乙酰氧基木聚糖酯酶，二-O-乙酰化甲基β-D-吡喃吡喃糖苷的2-脱氧，3-脱氧，2-脱氧-2-氟和3-脱氧-3-氟衍生物的四种修饰底物-脱水戊吡喃糖苷前体。通过三个步骤将甲基2,3-脱水-4-O-苄基-β-D-核吡喃糖苷转化为甲基2,3-脱水-4-O-苄基-β-D-核吡喃糖苷。通过氢化物还原或氢氟化来完成2，3-脱水戊基吡喃糖苷的环氧开环。测试了β-D-吡喃吡喃二甲基2,3,4-tri-O-，2,4-di-O-和3,4-di-O-乙酸酯和制备的二乙酸酯类似物作为乙酰木聚糖酯酶底物的来源裂褶菌公社和里氏木霉。其脱乙酰基速率的测量指出了底物酶的独特结构要求。
• Studies toward the Total Synthesis of Nogalamycin: Construction of the Complete ABCDEF-Ring System via a Convergent Hauser Annulation
  作者：Ruogu Peng、Michael S. VanNieuwenhze

  DOI：10.1021/acs.joc.8b02602

  日期：2019.1.18

  The convergent synthesis of the complete ABCDEF-ring system within nogalamycin, an anthracycline natural product, was studied. The pivotal Hauser annulation for the anthraquinone core construction was achieved by the fusion of two highly functionalized segments: a cyanophthalide (the AB-ring segment) and a tricyclic quinone monoketal (the DEF-ring segment). Key transformations toward the AB-ring segment

  研究了蒽环类天然产物诺加霉素内完整ABCDEF-环系统的收敛合成。蒽醌核心结构的关键Hauser环空反应是通过两个高度官能化的链段的融合而实现的：氰基酞酸酯（AB环链段）和三环醌单缩酮（DEF环链段）。向AB环段的关键转变包括对映选择性烯醇化α-羟基化，非对映选择性氢硼化-氧化和定向芳族锂化-甲酰化。为了制备用于环化的DEF-环链段，使用了由（二乙酰氧基碘）苯（PIDA）对F-环苯酚基团进行的轻度脱芳香化作用。
• Transposition de l'atome d'azote de dialkylaminopentopyranosides; mise en evidence de sels d'aziridinium intermediaires
  作者：D. Picq、M. Cottin、D. Anker、H. Pacheco

  DOI：10.1016/s0040-4020(01)88690-7

  日期：1983.1

  Methyl pyranosides with dimethylamino and sulfonyloxy groups in trans relationship undergo rearrangement with participation of the dimethylamino group. This rearrangement results in a 1,2-shift of the nitrogen function which is assumed to be concerted in apolar solvents such as benzene. On the contrary, in water the shift proceeds via an aziridinium ion (observed by NMR) which is opened in a second

  具有反式关系的二甲基氨基和磺酰氧基的甲基吡喃糖苷在二甲基氨基的参与下发生重排。这种重排导致氮官能团发生1,2-移位，这被认为在非极性溶剂（如苯）中是一致的。相反，在水中，该位移通过在第二步中打开的叠氮鎓离子（通过NMR观察）进行，与水或亲核试剂的收率很高。叠氮鎓离子的开口具有与相应的环氧化物相同的区域选择性。