phenyl 2,6-di-O-benzyl-3,4-di-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-β-D-glucopyranoside | 795305-88-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,6-di-O-benzyl-3,4-di-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-β-D-glucopyranoside
• 英文别名: phenyl 2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-yl]-1-thio-β-D-glucopyranoside；phenyl 2,6-O-benzyl-3,4,O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-β-D-glucopyranoside；(2S,3S,4aR,5R,7S,8R,8aS)-2,3-dimethoxy-2,3-dimethyl-8-phenylmethoxy-5-(phenylmethoxymethyl)-7-phenylsulfanyl-5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxine
• CAS: 795305-88-3
• 化学式: C₃₂H₃₈O₇S
• 分子量: 566.716
• InChiKey: CDYSXNWBNNDZHN-KIFILCCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  89.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  phenyl 2,6-di-O-benzyl-3,4-di-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-β-D-glucopyranoside 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以91%的产率得到phenyl 2,6-di-O-benzyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Stereocontrolled Formation of β-Glucosides and Related Linkages in the Absence of Neighboring Group Participation:  Influence of a trans-Fused 2,3-O-Carbonate Group

  摘要：

  [GRAPHICS]Phenyl 4,6-di-O-benzyl-2,3-O-carbonyl-beta-D-glucothiopyranoside and the regiosiomeric phenyl 2,6-di-O-benzyl-3,4-O-carbonyl-beta-D-glucothiopyranoside were prepared and studied as glucosyl donors at -60 degrees C in dichloromethane with preactivation by 1-benzenesulfinyl piperidine before addition of the acceptor alcohol. The 2,3-O-carbonate protected donor showed moderate to excellent beta-selectivity under these conditions depending on the acceptor employed, thereby providing a means for 1,2-trans-equatorial glycosidic bonds without recourse to neighboring group participation and its associated problem of ortho ester formation. In contrast, the 3,4-O-carbonate protected donor showed moderate to no beta-selectivity under the conditions employed. The results obtained in this study with carbonate protected glucopyranosyl donors are contrasted with those obtained previously in the manno- and rhamnopyranosyl series when the 2,3-O-carbonate protected is (x-selective and the 3,4-O-carbonate is beta-selective.

  DOI：

  10.1021/jo0508999
• 作为产物：
  描述：

  1-硫代-b-D-吡喃葡萄糖苷对甲苯酯 在 camphor-10-sulfonic acid 、 sodium hydride 、 原甲酸三甲酯 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.17h， 生成 phenyl 2,6-di-O-benzyl-3,4-di-O-(2,3-dimethoxybutane-2,3-diyl)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Stereocontrolled Formation of β-Glucosides and Related Linkages in the Absence of Neighboring Group Participation:  Influence of a trans-Fused 2,3-O-Carbonate Group

  摘要：

  [GRAPHICS]Phenyl 4,6-di-O-benzyl-2,3-O-carbonyl-beta-D-glucothiopyranoside and the regiosiomeric phenyl 2,6-di-O-benzyl-3,4-O-carbonyl-beta-D-glucothiopyranoside were prepared and studied as glucosyl donors at -60 degrees C in dichloromethane with preactivation by 1-benzenesulfinyl piperidine before addition of the acceptor alcohol. The 2,3-O-carbonate protected donor showed moderate to excellent beta-selectivity under these conditions depending on the acceptor employed, thereby providing a means for 1,2-trans-equatorial glycosidic bonds without recourse to neighboring group participation and its associated problem of ortho ester formation. In contrast, the 3,4-O-carbonate protected donor showed moderate to no beta-selectivity under the conditions employed. The results obtained in this study with carbonate protected glucopyranosyl donors are contrasted with those obtained previously in the manno- and rhamnopyranosyl series when the 2,3-O-carbonate protected is (x-selective and the 3,4-O-carbonate is beta-selective.

  DOI：

  10.1021/jo0508999

文献信息

• β-Selective glucosylation in the absence of neighboring group participation: influence of the 3,4-O-bisacetal protecting system
  作者：David Crich、Venkataraman Subramanian、Thomas K. Hutton

  DOI：10.1016/j.tet.2007.03.128

  日期：2007.6

  A 3,4-O-bisacetal 2,6-di-O-benzyl protected thioglucoside is converted to the corresponding glucosyl triflate with 1-benzenesulfinyl piperidine and trifluoromethanesulfonic anhydride. The moderate to excellent beta-selectivity exhibited with this glucosyl triflate with a range of alcohols is generally higher than that observed with the more electronically disarmed corresponding 3,4-O-carbonate, for which a possible reason is advanced. (c) 2007 Elsevier Ltd. All rights reserved.
• Stereocontrolled Formation of β-Glucosides and Related Linkages in the Absence of Neighboring Group Participation:  Influence of a <i>trans</i>-Fused 2,3-<i>O</i>-Carbonate Group
  作者：David Crich、Prasanna Jayalath

  DOI：10.1021/jo0508999

  日期：2005.9.1

  [GRAPHICS]Phenyl 4,6-di-O-benzyl-2,3-O-carbonyl-beta-D-glucothiopyranoside and the regiosiomeric phenyl 2,6-di-O-benzyl-3,4-O-carbonyl-beta-D-glucothiopyranoside were prepared and studied as glucosyl donors at -60 degrees C in dichloromethane with preactivation by 1-benzenesulfinyl piperidine before addition of the acceptor alcohol. The 2,3-O-carbonate protected donor showed moderate to excellent beta-selectivity under these conditions depending on the acceptor employed, thereby providing a means for 1,2-trans-equatorial glycosidic bonds without recourse to neighboring group participation and its associated problem of ortho ester formation. In contrast, the 3,4-O-carbonate protected donor showed moderate to no beta-selectivity under the conditions employed. The results obtained in this study with carbonate protected glucopyranosyl donors are contrasted with those obtained previously in the manno- and rhamnopyranosyl series when the 2,3-O-carbonate protected is (x-selective and the 3,4-O-carbonate is beta-selective.
• Design and Synthesis of 5‘-Deoxy-5‘-Phenyladenophostin A, a Highly Potent IP₃ Receptor Ligand¹
  作者：Tetsuya Mochizuki、Yoshihiko Kondo、Hiroshi Abe、Colin W. Taylor、Barry V. L. Potter、Akira Matsuda、Satoshi Shuto

  DOI：10.1021/ol0602710

  日期：2006.3.1

  5'-Deoxy-5'-phenyladenophostin A (5), designed as a useful IP3 receptor ligand based on the previous structure-activity relationship studies, was successfully synthesized via two key stereoselective glycosidation steps. This compound proved to be a highly potent IP3 receptor agonist.