3,4,6-tri-O-benzyl-D-glucono-1,5-lactone | 205502-41-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6-tri-O-benzyl-D-glucono-1,5-lactone
• 英文别名: 3,4,6-tri-O-benzyl-D-glucolactone；3,4,6-tri-O-benzyl-D-gluconolactone；(3R,4R,5R,6R)-3-hydroxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-one
• CAS: 205502-41-6
• 化学式: C₂₇H₂₈O₆
• 分子量: 448.516
• InChiKey: FRWRDFOHUINWHU-VEYUFSJPSA-N

物化性质

• 沸点：
  610.0±55.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-benzyl-D-glucono-1,5-lactone 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 生成 (2S,3S,4R,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-prop-1-en-2-yloxan-3-ol
  参考文献：
  名称：

  Highly Stereoselective Hydroformylation of Olefins Possessing Chiral Sugar Templates

  摘要：

  具有手性糖模板的1,1-二取代烯烃的氢羰基化反应，以良好至优异的产率得到了β-取代的醛，最高达99%的非对映选择性。

  DOI：

  10.1055/s-1998-1680
• 作为产物：
  描述：

  3,4,6-tri-O-benzyl-D-glucopyranose 在 吡啶 、 N-(2,2,6,6-tetramethyl-1-oxopiperidin-1-ium-4-yl)acetamide tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到3,4,6-tri-O-benzyl-D-glucono-1,5-lactone
  参考文献：
  名称：

  氧铵盐。第8部分：碱中的氧化：使用4-乙酰氨基-2,2,6,6-四甲基哌啶-1-氧代四氟硼酸O-1将未保护的O-1单糖氧化为内酯

  摘要：

  据报道，吡啶/ CH 2 Cl 2中的氧化剂4-乙酰氨基-2,2,6,6-四甲基哌啶-氧铵四氟硼酸酯是将半缩醛转化为内酯的极佳试剂。具体地，以高收率实现了1-O未保护的糖向其相应的醛糖内酯的转化。碱性反应条件部分地克服了对于氧铵型氧化剂报道的一些缺点，即在酸不稳定基团和β-氧存在下不能进行反应。

  DOI：

  10.1016/s0040-4039(01)01950-5

文献信息

• Oxoammonium salts. Part 8: Oxidations in base: oxidation of O-1 unprotected monosaccharides to lactones using 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate
  作者：Nabyl Merbouh、James M Bobbitt、Christian Brückner

  DOI：10.1016/s0040-4039(01)01950-5

  日期：2001.12

  The oxidant, 4-acetylamino-2,2,6,6-tetramethylpiperidine-oxoammonium tetrafluoroborate in pyridine/CH2Cl2, is reported to be an excellent reagent for the conversion of hemiacetals to lactones. Specifically, the conversion of 1-O unprotected sugars to their corresponding aldonolactones is achieved in high yields. The basic reaction conditions partially overcome some disadvantages reported for oxoammonium-type

  据报道，吡啶/ CH 2 Cl 2中的氧化剂4-乙酰氨基-2,2,6,6-四甲基哌啶-氧铵四氟硼酸酯是将半缩醛转化为内酯的极佳试剂。具体地，以高收率实现了1-O未保护的糖向其相应的醛糖内酯的转化。碱性反应条件部分地克服了对于氧铵型氧化剂报道的一些缺点，即在酸不稳定基团和β-氧存在下不能进行反应。
• A Fries-Type Rearrangement Strategy for the Construction of Stereodefined Quaternary Pseudoanomeric Centers: An Entry into <i>C</i>-Naphthyl Ketosides
  作者：Haijuan Liu、Mylène Lang、Damien Hazelard、Philippe Compain

  DOI：10.1021/acs.joc.3c01474

  日期：2023.10.6

  The stereodefined construction of quaternary pseudoanomeric centers by way of a BF3·Et2O-catalyzed, Fries-type rearrangement of O-ketosides is described. This method provides new access to C-naphthyl ketosides related to biologically relevant products with good to complete stereocontrol in favor of the β product.

  描述了通过 BF 3 ·Et 2 O-催化、O-酮苷的弗里斯型重排来立体定义的四元假异头中心的构建。该方法提供了与生物相关产品相关的C-萘基酮苷的新途径，并具有有利于β产品的良好至完整的立体控制。
• Synthesis of 1-deoxyhept-2-ulosyl-glycono-1,5-lactone utilizing α-selective O-glycosidation of 2,6-anhydro-1-deoxy-d-hept-1-enitols
  作者：Rie Namme、Takashi Mitsugi、Hideyo Takahashi、Moto Shiro、Shiro Ikegami

  DOI：10.1016/j.tet.2006.07.032

  日期：2006.9

  A series of 1-deoxy-heptulo-2-pyranosyl-glycono-1,5-lactones were synthesized utilizing completely a-selective O-glycosidation of heptenitols. Anomeric configuration of the products was confirmed by (3)J(C,H) coupling measurement and X-ray crystal structural analysis. The benzyl-protected ketosyl saccharides were partly unstable, and glycosidic linkage was prone to cleave under the usual debenzylation conditions. To prevent this, we surveyed various additives for the Pd-catalyzed hydrogenation reaction and found that basic alumina was the most effective. (c) 2006 Elsevier Ltd. All rights reserved.
• Highly Stereoselective Hydroformylation of Olefins Possessing Chiral Sugar Templates
  作者：Takashi Takahashi、Satoshi Ebata、Haruo Yamada

  DOI：10.1055/s-1998-1680

  日期：1998.4

  Hydroformylation of 1,1-disubstituted olefins possessing chiral sugar templates gave β-substituted aldehydes in good to excellent yields with up to 99% diastereoselectivity.

  具有手性糖模板的1,1-二取代烯烃的氢羰基化反应，以良好至优异的产率得到了β-取代的醛，最高达99%的非对映选择性。
• Diastereoselective access to <i>C</i>,<i>C</i>-glycosyl amino acids <i>via</i> iron-catalyzed, auxiliary-enabled MHAT coupling
  作者：Mylène Lang、Damien Tardieu、Benoit Pousse、Philippe Compain、Nicolas Kern

  DOI：10.1039/d3cc06249j

  日期：2024.3.14

  Novel C,C-glycosyl amino acids were accessed by means of an iron-catalyzed hydrogen atom transfer sequence. Crucially, two-fold diastereocontrol could be achieved in the ‘matched’ coupling of exo-d-glycals with an enantiopure dehydroalanine acceptor.