benzyl 2,3-O-isopropylidene-6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside | 91652-71-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2,3-O-isopropylidene-6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside
• 英文别名: benzyl 6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-α-D-mannopyranoside；(3aS,4S,6R,7R,7aS)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-4-phenylmethoxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol
• CAS: 91652-71-0
• 化学式: C₃₂H₄₀O₆Si
• 分子量: 548.751
• InChiKey: NBZXITPOHSIBIQ-ZNOUKXQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.39
• 重原子数：
  39.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  benzyl 2,3-O-isopropylidene-6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside 在 偶氮二异丁腈 、 水 、 三正丁基氢锡 、 sodium hexamethyldisilazane 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.33h， 生成 (2S,3S,4S,6S)-2-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3,4-diol
  参考文献：
  名称：

  Grignard additions to 2-uloses: synthesis of stereochemically pure tertiary alcohols

  摘要：

  The addition of Grignard reagents to a number of 2-uloses has been investigated. Despite initial low diastereoselectivities it was found that tuning the ketone starting materials and studying solvent effects allowed formation of a single alcohol product. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.02.106
• 作为产物：
  描述：

  D-甘露糖 在 咪唑 、 camphor-10-sulfonic acid 、 乙酰氯 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 47.5h， 生成 benzyl 2,3-O-isopropylidene-6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of the α-Mannosidase inhibitors swainsonine [(1S, 2R, 8R, 8aR)-1,2,8-trihydroxyoctahydroindolizine] and 1,4-dideoxy-1,4-imino-d-mannitol from mannose

  摘要：

  DOI：

  10.1016/s0040-4020(01)86850-2

文献信息

• Comparative investigations on the regioselective mannosylation of 2,3,4-triols of mannose
  作者：Piotr Cmoch、Zbigniew Pakulski

  DOI：10.1016/j.tetasy.2008.05.032

  日期：2008.6

  Regioselective glycosylation of 2,3,4-unprotected benzyl alpha-D-mannopyranoside and allyl alpha- and -beta-D-mannopyranosides has been investigated. The configuration at the anomeric centre influences the outcome of the reaction. Possible role of hydrogen-bonding network in glycosylation of the above triols used as glycosidic acceptors is discussed. (C) 2008 Elsevier Ltd. All rights reserved.
• Enantiospecific Synthesis of Swainsonine, (1S, 2R, 8R, 8aR)-1,2,8-trihydroxyoctahydroindolizine, from D-mannose
  作者：G.W.J. Fleet、M.J. Gough、P.W. Smith

  DOI：10.1016/s0040-4039(01)90059-0

  日期：——
• Four-component one-pot synthesis of a branched manno-pentasaccharide: tert-butyldiphenylsilyl ether as an in situ removable carbohydrate-protecting group
  作者：Swarbhanu Sarkar、Samrat Dutta、Gora Das、Asish Kumar Sen

  DOI：10.1016/j.tet.2011.03.109

  日期：2011.6

  A branched mannose-pentasaccharide was synthesized in a convergent one-pot sequence involving chemo- and regioselective glycosylations of suitable acceptors and in situ removal of tert-butyldiphenylsilyl group. The process demonstrated that a combination of TMSOTf and TfOH can be used as an effective reagent for the fast and selective in situ de-protection of tert-butyldiphenylsilyl group, and also serve as part of the promoter system for the subsequent glycosylation reaction. (C) 2011 Elsevier Ltd. All rights reserved.
• BASHYAL, BHARAT P.;FLEET, GEORGE W. J.;GOUGH, MAX J.;SMITH, PAUL W., TETRAHEDRON, 43,(1987) N 13, 3083-3093
  作者：BASHYAL, BHARAT P.、FLEET, GEORGE W. J.、GOUGH, MAX J.、SMITH, PAUL W.

  DOI：——

  日期：——