C-β,β-trehalose peracetate | 130168-59-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: C-β,β-trehalose peracetate
• 英文别名: bis(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)methane；[(2R,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-[[(2S,3S,4R,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]methyl]oxan-2-yl]methyl acetate
• CAS: 130168-59-1
• 化学式: C₂₉H₄₀O₁₈
• 分子量: 676.626
• InChiKey: YXQBHLQYIAPMHC-ZGJSJIGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  47
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  229
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  C-β,β-trehalose peracetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 bis(β-D-glucopyranosyl)methane
  参考文献：
  名称：

  Synthesis and Partial Biological Evaluation of a Small Library of Differentially-Linked β-C-Disaccharides¹

  摘要：

  The synthesis of a small library of differentially-linked beta-C-disaccharides has been carried out through the use of a radical allylation-RCM strategy. Acids 6 were prepared by Keck allylation of a suitable carbohydrate-based radical precursor, followed by oxidative cleavage of the formed alkene. Dehydrative coupling of these acids with the known olefin alcohol 5 then gave the precursor esters 7 in excellent yield. Methylenation of the esters 7 was followed by RCM and in situ hydroboration-oxidation of the formed glycals to furnish the protected beta-C-disaccharides 10 in good overall yield. Five examples were then deprotected and screened for their efficacy as enzyme inhibitors of beta-glycosidase and against several solid-tumor cell lines for in vitro differential cytotoxicity.

  DOI：

  10.1021/jo030039x
• 作为产物：
  描述：

  bis(β-D-glucopyranosyl)nitromethane peracetate 在 偶氮二异丁腈 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以76%的产率得到C-β,β-trehalose peracetate
  参考文献：
  名称：

  Synthesis and conformational studies of .beta.-(1.fwdarw.6)- and .beta.,.beta.-(1.fwdarw.1)-linked C-disaccharides

  摘要：

  An expeditious methodology for the synthesis of beta-(1-->6)- and beta,beta-(1-->1)-linked C-disaccharides has been developed. The methodology is based on the fluoride ion-mediated coupling of the (base-stable) nitronate anion derived from a glycosylnitromethane (1) and an aldehydo-hexodialdose or -hexose derivative. The carba-analogs (methylene-bridged analogs) of beta-D-Glc-(1-->6)-D-Gal and of beta,beta-trehalose (beta-D-Glc-(1-->1)-beta-D-Glc) were thus obtained in six steps only from 1 and D-galactose-derived aldehyde 4 or aldehydo-D-glucose derivative 12, respectively. The preferred conformation of the (1-->1)-linked C-disaccharides, including the symmetrical C-beta,beta-trehalose, was established on the basis of the vicinal coupling constants about the interglycosidic C-C linkages. In all the compounds of this series, the beta-C-glycosidic linkages were found to adopt preferentially the ''anti'' conformation (C2-C1-C7-C1' torsional angle = approximately 180-degrees). Our studies revealed, in particular, that the solution conformation of C-beta,beta-trehalose, in which no stereoelectronic (exo-anomeric) effects are operating, is the same as the one predicted and determined for beta,beta-trehalose, thereby demonstrating that steric effects alone are sufficient to cause the greater stability of the preferred conformation of the parent disaccharide.

  DOI：

  10.1021/jo00053a033

文献信息

• 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)
• Ramberg-Bäcklund Approaches to the Synthesis of C-Linked Disaccharides
  作者：Frank K. Griffin、Duncan E. Paterson、Richard J. K. Taylor

  DOI：10.1002/(sici)1521-3773(19991004)38:19<2939::aid-anie2939>3.0.co;2-s

  日期：1999.10.4

  Readily available S-glycoside dioxides were utilized in a Ramberg-Bäcklund rearrangement for the construction of C-linked disaccharides. This approach is ideally suited to analogue synthesis simply by variation of the alkylating agent, and is illustrated here by the synthesis of beta,beta-C-trehalose (see reaction scheme), a higher homologue of C-trehalose, and methyl C-gentiobioside. Bn=benzyl.

  在Ramberg-Bäcklund重排中利用了现成的S-糖苷二氧化物来构建C键联的二糖。这种方法非常适合简单地通过烷基化剂的变化进行类似物合成，并且在此处通过β，β-C-海藻糖的合成（请参见反应方案），C-海藻糖的较高同源物和甲基C-龙胆生物苷进行说明。 。Bn ＝苄基。
• A concise approach to .beta.-(1.fwdarw.6)- and .beta.,.beta.-(1.fwdarw.1)-linked C-disaccharides. The synthesis of C-.beta.,.beta.-trehalose peracetate
  作者：Olivier R. Martin、Wen Lai

  DOI：10.1021/jo00305a004

  日期：1990.8