3,4,5,7-tetra-O-benzyl-α-D-gluco-hept-2-ulopyranose | 85398-14-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,5,7-tetra-O-benzyl-α-D-gluco-hept-2-ulopyranose
• 英文别名: (2S,3R,4S,5R,6R)-2-(hydroxymethyl)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-ol
• CAS: 85398-14-7
• 化学式: C₃₅H₃₈O₇
• 分子量: 570.683
• InChiKey: WGFUUMQJBZIOKC-KJQSSVQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,4,5,7-tetra-O-benzyl-α-D-gluco-hept-2-ulopyranose 在 吡啶 、 三乙基硅烷 、 三氟化硼乙醚 、 trityl tetrafluoroborate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 14.0h， 生成 2,6-anhydro-3,4,5-tri-O-benzyl-1-O-(trimethylacetyl)-D-glycero-D-gulo-heptitol
  参考文献：
  名称：

  Conversion of D-glucose to L-glucose: oxidative decarboxylation of .alpha.-oxycarboxylic acids via their diacyl peroxides

  摘要：

  D-Glucose was converted to an L-glucose derivative. The key step was the oxidative decarboxylation of carboxylic acid 12 via its diacyl peroxide derivative. This synthetic scheme proceeds through C-glycosidic compounds and is applicable to other sugar configurations.

  DOI：

  10.1021/jo00002a009
• 作为产物：
  描述：

  methyl 3,4,5,7-tetra-O-benzyl-α-D-gluco-2-heptulopyranoside 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以87%的产率得到3,4,5,7-tetra-O-benzyl-α-D-gluco-hept-2-ulopyranose
  参考文献：
  名称：

  Conversion of D-glucose to L-glucose: oxidative decarboxylation of .alpha.-oxycarboxylic acids via their diacyl peroxides

  摘要：

  D-Glucose was converted to an L-glucose derivative. The key step was the oxidative decarboxylation of carboxylic acid 12 via its diacyl peroxide derivative. This synthetic scheme proceeds through C-glycosidic compounds and is applicable to other sugar configurations.

  DOI：

  10.1021/jo00002a009

文献信息

• Synthetic applications of Ramberg-Bäcklund derived exo-glycals
  作者：Marie-Lyne Alcaraz、Frank K. Griffin、Duncan E. Paterson、Richard J.K. Taylor

  DOI：10.1016/s0040-4039(98)01823-1

  日期：1998.10

  title glycals, prepared from S-glycoside dioxides using the Meyers' variant of the Ramberg-Bäcklund rearrangement are described. These include a formal total synthesis of a novel β-glycosidase inhibitor, and an efficient route to spirocyclic glucose derivatives. In addition, silyl methodology has been developed which allows unprotected exo-glycals to be synthesised.

  描述了使用Ramberg-Bäcklund重排的Meyers'变体由S-糖苷二氧化物制备的标题糖的合成应用。这些包括新型β-糖苷酶抑制剂的正式全合成，以及获得螺环葡萄糖衍生物的有效途径。另外，已经开发了甲硅烷基方法，其允许合成未保护的外糖。
• Desoxy-nitrozucker. 3. Mitteilung. Synthese von Ketosen durch Kettenverlängerung von 1-Desoxy-1-nitro-aldosen. Nucleophile Additionen und Solvolyse von Nitroaethern
  作者：Bernard Aebischer、Jost H. Bieri、Roland Prewo、Andrea Vasella

  DOI：10.1002/hlca.19820650730

  日期：1982.11.3

  Synthesis of Ketoses by Chain Elongation of 1-Deoxy-1-nitroaldoses. Nucleophilic Additions and Solvolysis of Nitro Ethers

  通过1-脱氧-1-硝基醛糖的链延伸合成酮酶。硝基醚的亲核加成和溶剂分解
• A Ramberg−Bäcklund Approach to the Synthesis ofC-Glycosides,C-Linked Disaccharides, andC-Glycosyl Amino Acids
  作者：Duncan E. Paterson、Frank K. Griffin、Marie-Lyne Alcaraz、Richard J. K. Taylor

  DOI：10.1002/1099-0690(200204)2002:7<1323::aid-ejoc1323>3.0.co;2-8

  日期：2002.4

  dioxides using the Meyers variant of the Ramberg−Backlund rearrangement, are described. These include a formal synthesis of a β-glycosidase inhibitor 12 and an efficient route to spirocyclic glucose derivatives 17 and 18. The synthesis of C-linked disaccharides 24, 31, and 38 and the C-glycosyl amino acid 49 using the Ramberg−Backlund rearrangement is also reported. (© Wiley-VCH Verlag GmbH, 69451 Weinheim

  描述了使用 Ramberg-Backlund 重排的 Meyers 变体衍生自 S-糖苷二氧化物的外糖的合成应用。其中包括 β-糖苷酶抑制剂 12 的正式合成和生成螺环葡萄糖衍生物 17 和 18 的有效途径。 使用 Ramberg-Backlund 合成 C-连接的二糖 24、31 和 38 和 C-糖基氨基酸 49重排也有报道。(© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)
• Highly Efficient Synthesis of Ketoheptoses
  作者：Daniel Waschke、Julian Thimm、Joachim Thiem

  DOI：10.1021/ol2012764

  日期：2011.7.15

  A reliable, facile, high overall yielding and diastereoselective synthesis of ketoheptoses was developed and applied for preparation of the two most diabetogenic ketoheptoses as well as in a modified version for the synthesis of kamusol.
• Regioselective synthesis and biological evaluation of spiro-sulfamidate glycosides from exo-glycals
  作者：Mahmoud Benltifa、Miklos De Kiss、Maria Isabel Garcia-Moreno、Carmen Ortiz Mellet、David Gueyrard、Anne Wadouachi

  DOI：10.1016/j.tetasy.2009.07.012

  日期：2009.8

  We report the synthesis of spiro-sulfamidate glycosides from exo-glycals. This route is regioselective and furnishes an original class of spiro-hydantoin glycoside analogues. A biological evaluation of this family on a range of glycosidases shows that these compounds are weak but very selective inhibitors of a-glucosidase and amyloglucosidase. (c) 2009 Elsevier Ltd. All rights reserved.