methyl 2,3-anhydro-6-O-benzoyl-α-D-glucopyranoside | 114768-48-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-anhydro-6-O-benzoyl-α-D-glucopyranoside
• 英文别名: methyl 2,3-anhydro-6-O-benzoyl-α-D-allopyranoside；[(1R,2S,4R,5R,6R)-5-hydroxy-2-methoxy-3,7-dioxabicyclo[4.1.0]heptan-4-yl]methyl benzoate
• CAS: 114768-48-8
• 化学式: C₁₄H₁₆O₆
• 分子量: 280.277
• InChiKey: ACIVZKQDWRKWAY-SKENRDBWSA-N

物化性质

• 沸点：
  442.3±45.0 °C(predicted)
• 密度：
  1.35±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2,3-anhydro-6-O-benzoyl-α-D-glucopyranoside 生成 methyl 2,3-anhydro-6-O-benzoyl-4-O-methylsulphonyl-α-D-allopyranoside
  参考文献：
  名称：

  AL-MASOUDI, NAJIM A. L.;HUGHES, NEIL A., J. CHEM. SOC. PERKIN TRANS., 1,(1987) N 9, 2061-2067

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 2,3-anhydro-α-D-allopyranoside 生成 methyl 2,3-anhydro-6-O-benzoyl-α-D-glucopyranoside
  参考文献：
  名称：

  AL-MASOUDI, NAJIM A. L.;HUGHES, NEIL A., J. CHEM. SOC. PERKIN TRANS., 1,(1987) N 9, 2061-2067

  摘要：

  DOI：

文献信息

• Syntheses of 6-Deoxyhex-5-enopyranosides from 6-Bromo-6-deoxy- or 6-<i>O</i>-<i>p</i>-Tolylsulfonylhexopyranosides by the Use of DBU in DMSO
  作者：Ken-ichi Sato、Noriyuki Kubo、Ritsuko Takada、Shogo Sakuma

  DOI：10.1246/bcsj.66.1156

  日期：1993.4

  Various kinds of nonbranched and methyl-branched 6-deoxyhex-5-enopyranoside derivatives were prepared from 6-bromo-6-deoxy or 6-O-p-tolylsulfonylhexopyranoside in a one-pot procedure by a successive treatment with iodide anion and 1,8-diazabicyclo[5.4.0]undec-7-ene in dimethyl sulfoxide. The scope and limitations of this reaction have become apparent by observing the reactions of 18 substrates. The yields of altropyranoside and 2-deoxyribo-hexopyranoside derivatives were high, except for the 2,3-anhydropyranoside derivative. Methyl-branched 6-deoxyhex-5-enopyranoside derivatives were also obtained in practical yields.

  各种非分支和甲基分支的6-脱氧己-5-烯吡喃苷衍生物是通过将6-溴-6-脱氧或6-O-对甲苯磺酰己吡喃苷与碘离子及1,8-二氮杂双环[5.4.0]十一烯在二甲基亚砜中进行连续处理，采用一锅法制备的。通过观察18种底物的反应，这一反应的范围和局限性变得明显。除了2,3-无水吡喃苷衍生物外，其他的反应产物（如altropyranoside和2-脱氧核糖己吡喃苷衍生物）产率较高。甲基分支的6-脱氧己-5-烯吡喃苷衍生物也以实用的产率获得。
• A synthetic study of methyl 3-deoxy-3-fluoro-α-d-glucopyranosides from methyl 2,3-anhydro-α-d-allopyranosides, and synthesis of 3′-deoxy-3′-fluorokanamycin A and 3′-chloro-3′-deoxykanamycin A
  作者：Eijiro Umemura、Tsutomu Tsuchiya、Yoshihiko Kobayashi、Koichi Tanaka

  DOI：10.1016/0008-6215(92)84101-w

  日期：1992.2

  utilized to measure the effects of solvation and hydrogen bonding relative to the C-4 and C-6 substituents. By application of this reaction, 3′-deoxy-3′-fluorokanamycin A has been prepared by treatment of a 2′,3′-anhydro-3′-epikanamycin A derivative ( 35 ) with KHF 2 . 3′-Chloro-3′-deoxykanamycin A was also prepared.

  摘要在环氧乙烷-1，2-二醇中，4，6-二取代的2，3-脱水-α-d-吡喃果糖苷与氟化氢钾（KHF 2）反应通过环氧乙烷环开环得到相应的2-脱氧-2-氟代-α-d-氨基和3-脱氧-3-氟代-α-d-葡萄糖基吡喃糖基衍生物，后者总是占优势。通过分子力学研究了C-4和C-6处取代基对d-葡萄糖-d-altro（r）的影响，并积极利用实验值和计算值r的差异来衡量效果相对于C-4和C-6取代基的溶剂化和氢键的关系。通过应用该反应，通过用KHF 2处理2′，3′-脱水-3′-表卡那霉素A衍生物（35），制备了3′-脱氧-3′-氟卡那霉素A。还制备了3'-氯-3'-脱氧卡那霉素A。
• Oxidative Cleavage of 4,6-<i>O</i>-Benzylidene Ring with t-Butyl Hydroperoxide and Copper(II) Chloride. Preparation of Methyl 4-<i>O</i>- and 6-<i>O</i>-Benzoylhexopyranoside Derivatives
  作者：Ken-ichi Sato、Tetsutaro Igarashi、Yukio Yanagisawa、Nobuya Kawauchi、Hironobu Hashimoto、Juji Yoshimura

  DOI：10.1246/cl.1988.1699

  日期：1988.10.5

  Copper(II) chloride and palladium(II) acetate were found to be highly effective catalysts for oxidative cleavage of O-benzylidene ring with t-butyl hydroperoxide. Using the former catalyst 4,6-O-benzylidenehexopyranoside derivatives were converted into the corresponding 4- and 6-benzoates in high yields. This reaction was also applicable for conversion of benzyl group into benzoyl one.

  发现氯化铜 (II) 和乙酸钯 (II) 是使用叔丁基氢过氧化物氧化裂解 O-亚苄基环的高效催化剂。使用前一种催化剂，4,6-O-亚苄基己基吡喃糖苷衍生物以高产率转化为相应的4-和6-苯甲酸酯。该反应也适用于将苄基转化为苯甲酰基。
• Regioselective Oxidative Cleavage of Benzylidene Acetals of Glycopyranosides with Periodic Acid Catalyzed by Tetrabutylammonium Bromide
  作者：Jean-Michel Vatèle

  DOI：10.1055/s-0033-1340056

  日期：——

  A combination of periodic acid, tetrabutylammonium bromide, and wet alumina in dichloromethane efficiently oxidized benzylidene acetals of carbohydrates to the corresponding hydroxybenzoates in excellent yields (>90%). Under these conditions, other protecting groups, such as tert-butyl(dimethyl)silyl, tert-butyl(diphenyl)silyl, and functional groups, such as epoxide, were unaffected. By varying the

  高碘酸、溴化四丁基铵和湿氧化铝在二氯甲烷中的组合有效地将碳水化合物的亚苄基缩醛氧化为相应的羟基苯甲酸酯，产率极好 (>90%)。在这些条件下，其他保护基团（例如叔丁基（二甲基）甲硅烷基、叔丁基（二苯基）甲硅烷基）和官能团（例如环氧化物）不受影响。通过改变 C3 位置保护基团的性质，获得了对 4-或 6-苯甲酸酯的良好到高的区域选择性。
• Al-Masoudi, Najim A. L.; Hughes, Neil A., Journal of the Chemical Society. Perkin transactions I, 1987, p. 2061 - 2068
  作者：Al-Masoudi, Najim A. L.、Hughes, Neil A.

  DOI：——

  日期：——