cyclohexyl 6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside | 637034-68-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: cyclohexyl 6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
• 英文别名: (2R,3S,6S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-cyclohexyloxy-3,6-dihydro-2H-pyran-3-ol
• CAS: 637034-68-5
• 化学式: C₁₈H₃₄O₄Si
• 分子量: 342.551
• InChiKey: HBQYKVPJIGOHED-BBWFWOEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  cyclohexyl 6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 在 manganese(IV) oxide 、 异氰酸苯酯 、 三乙胺 作用下， 以 二氯甲烷 、 环己烷 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Filho, Joao R. de Freitas; Cottier, Louis; Srivastava, Rajendra M., Synlett, 2003, # 9, p. 1358 - 1360

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酰化葡萄烯糖 在 咪唑 、 montmorillonite K-10 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 cyclohexyl 6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  Filho, Joao R. de Freitas; Cottier, Louis; Srivastava, Rajendra M., Synlett, 2003, # 9, p. 1358 - 1360

  摘要：

  DOI：

文献信息

• Stereocontrolled palladium(0)-catalyzed preparation of unsaturated azidosugars: an easy access to 2- and 4-aminoglycosides
  作者：Ronaldo N. de Oliveira、Louis Cottier、Denis Sinou、Rajendra M. Srivastava

  DOI：10.1016/j.tet.2005.06.041

  日期：2005.8

  The palladium-catalyzed substitution of alkyl 4,6-di-O-acetyl-alpha-D-erythro-hex-2-eno-pyranosides using NaN3 as the nucleophile gave predominantly the corresponding alkyl 2-azido-2,3,4-trideoxy-alpha-D-threo-hex-2-enopyranosides in the presence of Pd(PPh3)(4). However, alkyl 6-O-acetyl-4-azido-2,3,4-trideoxy-alpha-D-erythro-hex-2-enopyranosi des were obtained as the major products using Pd(PPh3)4 as the catalyst in the presence of dppb as the added ligand. Conversely, alkyl 6-O-(tert-butyidimethylsilyl)-4-0-methoxycarbonyl-2,3-dideoxy-alpha-D-hex-2-enopyranosides gave exclusively alkyl 4-azido-6-O-(tert-butyldimethylsilyi)-2,3,4-trideoxy-alpha-D-erythro-hex-2-enopyranosides in the presence of Pd-2(dba)(3)/PPh3 as the catalyst and Me3SiN3 as the nucleophile. The bis-hydroxylation followed by hydrogenation of ethyl 4-azido-2,3,4-trideoxy-alpha-D-erythro-hex-2-enopyranoside afforded the corresponding 4-amino-alpha-D-mannopyranoside, when propyl 2-azido-2,3,4-trideoxy-alpha-D-threo-hex-3-enopyranoside gave the 2-amino-alpha-D-altropyranoside under the same conditions. (c) 2005 Elsevier Ltd. All rights reserved.