(3aS,3bS,6S,6aS,7aS)-6-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-tetrahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxol-5-one | 202063-30-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: (3aS,3bS,6S,6aS,7aS)-6-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-tetrahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxol-5-one
• 英文别名: (1S,2S,6S,8S,9S)-9-[tert-butyl(dimethyl)silyl]oxy-4,4-dimethyl-3,5,7,11-tetraoxatricyclo[6.3.0.02,6]undecan-10-one
• CAS: 202063-30-7
• 化学式: C₁₅H₂₆O₆Si
• 分子量: 330.453
• InChiKey: BLOHTVOLZHPJGW-XGZQDADWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3aS,3bS,6S,6aS,7aS)-6-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-tetrahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxol-5-one 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 0.08h， 生成 5-O-tert-butyldimethylsilyl-7-deoxy-1,2,O-isopropylidene-β-L-glycero-D-manno-heptofuranose
  参考文献：
  名称：

  d-甘露糖醛酸内酯中的6 R-和6 S -6 C-甲基甘露糖。抑制磷酸葡萄糖变位酶和磷酸甘露糖异位酶：用于研究甘露糖初级代谢的药物

  摘要：

  6 S - 3和6 R - 6 6 C-甲基甘露糖的合成分别依赖于衍生自d-甘露糖醛酸内酯的完全和部分受保护的酮的相反和高度立体选择性还原。硼氢化钠还原甲硅烷基化的酮2伴随着甲硅烷基保护基团的完全迁移到新的立体异构中心。当在氯化铈（III）存在下进行还原时，甲硅烷基迁移被抑制。两种差向异构体都是磷酸葡萄糖变位酶和磷酸甘露糖突变酶的良好抑制剂，并且是磷酸己糖合酶的特异性抑制剂。这项工作证实了6 C-烷基己糖提供了一组有价值的，具有良好生物利用度的化合物，用于研究与糖磷酸酯的初级代谢有关的酶。-7-脱氧-2,3-的X射线晶体分析：5,6二ö异亚丙基α-L- -glycero- d -manno- heptofuranose 16进行报告。

  DOI：

  10.1016/s0957-4166(98)00492-3
• 作为产物：
  描述：

  D-mannofuranurono-6,3-lactone 在 吡啶 、 camphor-10-sulfonic acid 、 copper(II) sulfate 作用下， 反应 21.17h， 生成 (3aS,3bS,6S,6aS,7aS)-6-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-tetrahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxol-5-one
  参考文献：
  名称：

  Mannuronolactone acetonide: easy access to C-3 OH and C-5 OH of mannose

  摘要：

  The synthesis of D-mannuronolactone acetonide 1 is described from alginic acid and provides an efficient route for the manipulation at C-5 of mannose. Reduction gives a new acetonide of mannose, 1,2-O-isopropylidene-beta-D-mannofuranose which, on further acetonation, gives 1,2:5,6-di-O-isopropylidene-beta-D-mannofuranose [giving easy access to C-3 OH of mannose] together with a small amount of 1,2:3,5-di-O-isopropylidene-beta-D-mannofuranose. Some silylated derivatives of mannuronolactone allow immediate access to the C-6 of mannose. Such intermediates are likely to be of value in the synthesis of derivatives of mannose. (C) 1997 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00604-6

文献信息

• 6R- and 6S-6C-Methylmannose from d-mannuronolactone. Inhibition of phosphoglucomutase and phosphomannomutase: agents for the study of the primary metabolism of mannose
  作者：Angeles Martin、Mark P Watterson、Andrew R Brown、Faiqa Imtiaz、Bryan G Winchester、David J Watkin、George W.J Fleet

  DOI：10.1016/s0957-4166(98)00492-3

  日期：1999.1

  The syntheses of 6S-3 and 6R-6 6C-methylmannoses rely on opposite and highly stereoselective reductions of fully and partially protected ketones derived from d-mannuronolactone, respectively. Reduction of the silylated ketone 2 by sodium borohydride was accompanied by complete migration of the silyl protecting group to the new stereogenic centre; the silyl migration was suppressed when the reduction

  6 S - 3和6 R - 6 6 C-甲基甘露糖的合成分别依赖于衍生自d-甘露糖醛酸内酯的完全和部分受保护的酮的相反和高度立体选择性还原。硼氢化钠还原甲硅烷基化的酮2伴随着甲硅烷基保护基团的完全迁移到新的立体异构中心。当在氯化铈（III）存在下进行还原时，甲硅烷基迁移被抑制。两种差向异构体都是磷酸葡萄糖变位酶和磷酸甘露糖突变酶的良好抑制剂，并且是磷酸己糖合酶的特异性抑制剂。这项工作证实了6 C-烷基己糖提供了一组有价值的，具有良好生物利用度的化合物，用于研究与糖磷酸酯的初级代谢有关的酶。-7-脱氧-2,3-的X射线晶体分析：5,6二ö异亚丙基α-L- -glycero- d -manno- heptofuranose 16进行报告。
• Mannuronolactone acetonide: easy access to C-3 OH and C-5 OH of mannose
  作者：Mark P. Watterson、Angeles Martin、Thomas M. Krülle、Juan C. Estevez、George W.J. Fleet

  DOI：10.1016/s0957-4166(97)00604-6

  日期：1997.12

  The synthesis of D-mannuronolactone acetonide 1 is described from alginic acid and provides an efficient route for the manipulation at C-5 of mannose. Reduction gives a new acetonide of mannose, 1,2-O-isopropylidene-beta-D-mannofuranose which, on further acetonation, gives 1,2:5,6-di-O-isopropylidene-beta-D-mannofuranose [giving easy access to C-3 OH of mannose] together with a small amount of 1,2:3,5-di-O-isopropylidene-beta-D-mannofuranose. Some silylated derivatives of mannuronolactone allow immediate access to the C-6 of mannose. Such intermediates are likely to be of value in the synthesis of derivatives of mannose. (C) 1997 Published by Elsevier Science Ltd. All rights reserved.