<2'S,2''S,6'S,6''S> methyl 6-O-(tert-butyldiphenylsilyl)-3-O,4-O-(6',6''-diphenyloctahydro-2',2''-bipyran-2',2''-diyl)-α-D-glucopyranoside | 154859-11-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: <2'S,2''S,6'S,6''S> methyl 6-O-(tert-butyldiphenylsilyl)-3-O,4-O-(6',6''-diphenyloctahydro-2',2''-bipyran-2',2''-diyl)-α-D-glucopyranoside
• CAS: 154859-11-7
• 化学式: C₄₅H₅₄O₈Si
• 分子量: 751.004
• InChiKey: MZVUBURIAKVAAZ-OFDWYVBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.36
• 重原子数：
  54
• 可旋转键数：
  9
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  84.8
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 <2'S,2''S,6'S,6''S> methyl 6-O-(tert-butyldiphenylsilyl)-3-O,4-O-(6',6''-diphenyloctahydro-2',2''-bipyran-2',2''-diyl)-α-D-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 16.0h， 以94%的产率得到<2'S,2''S,6'S,6''S> methyl 2-O-acetyl-6-O-(tert-butyldiphenylsilyl)-3-O,4-O-(6',6''-diphenyloctahydro-2',2''-bipyran-2',2''-diyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Dispiroketals in synthesis (Part 17): Regioselective protection of D-glucopyranoside D-galactopyranoside and D-mannopyranoside substrates.

  摘要：

  Chiral recognition of enantiomeric trans-1,2-diol relationships leading to regioselective formation of 1,8,13,16-tetraoxadispiro[5.0.5.4] hexadecanes (dispiroketals) of various D-glucopyranoside, D-galactopyranoside and D-mannopyranoside substrates is described. Regioselectivity is achieved using the enantiomerically pure disubstituted tetrahydro-6,6'-bi-2H-pyrans 1, 2, 3, 4 and 5. Facile removal of the dispiroketal protecting group from a number of the sugar adducts has been achieved.

  DOI：

  10.1016/s0957-4166(00)80404-8
• 作为产物：
  描述：

  叔丁基二苯基氯硅烷 在 咪唑 、 camphor-10-sulfonic acid 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 46.0h， 生成 <2'S,2''S,6'S,6''S> methyl 6-O-(tert-butyldiphenylsilyl)-3-O,4-O-(6',6''-diphenyloctahydro-2',2''-bipyran-2',2''-diyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Dispiroketals in synthesis (Part 17): Regioselective protection of D-glucopyranoside D-galactopyranoside and D-mannopyranoside substrates.

  摘要：

  Chiral recognition of enantiomeric trans-1,2-diol relationships leading to regioselective formation of 1,8,13,16-tetraoxadispiro[5.0.5.4] hexadecanes (dispiroketals) of various D-glucopyranoside, D-galactopyranoside and D-mannopyranoside substrates is described. Regioselectivity is achieved using the enantiomerically pure disubstituted tetrahydro-6,6'-bi-2H-pyrans 1, 2, 3, 4 and 5. Facile removal of the dispiroketal protecting group from a number of the sugar adducts has been achieved.

  DOI：

  10.1016/s0957-4166(00)80404-8

文献信息

• Dispiroketals in synthesis (part 8): Regioselective protection of D-glucopyranose substrates
  作者：David A. Entwistle、Andrew B. Hughes、Steven V. Ley、Giuseppina Visentin

  DOI：10.1016/s0040-4039(00)75815-1

  日期：1994.1

  A new process for the efficient regioselective formation of 1,8,13,16-tetraoxadispiro[5.0.5.4]hexadecanes (dispiroketals) of various D-elucopyranosyl substrates by the chiral recognition of enantiomeric trans 1,2-diol relationships is described. This was achieved using the novel enantiomerically pure 2,2'-disubstituted 3,3',4,4'-tetrahydro-6,6'-bi-2H-pyrans 1, 2 and 11. New conditions for the removal of dispiroketal protecting groups are presented.
• Dispiroketals in synthesis (Part 17): Regioselective protection of D-glucopyranoside D-galactopyranoside and D-mannopyranoside substrates.
  作者：Paul J. Edwards、David A. Entwistle、Christophe Genicot、Steven V. Ley、Giuseppina Visentin

  DOI：10.1016/s0957-4166(00)80404-8

  日期：1994.12

  Chiral recognition of enantiomeric trans-1,2-diol relationships leading to regioselective formation of 1,8,13,16-tetraoxadispiro[5.0.5.4] hexadecanes (dispiroketals) of various D-glucopyranoside, D-galactopyranoside and D-mannopyranoside substrates is described. Regioselectivity is achieved using the enantiomerically pure disubstituted tetrahydro-6,6'-bi-2H-pyrans 1, 2, 3, 4 and 5. Facile removal of the dispiroketal protecting group from a number of the sugar adducts has been achieved.