methyl 2-O-(tert-butyldimethylsilyl)-β-D-xylofuranoside | 877466-16-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-O-(tert-butyldimethylsilyl)-β-D-xylofuranoside
• CAS: 877466-16-5
• 化学式: C₁₂H₂₆O₅Si
• 分子量: 278.421
• InChiKey: MWLNZCCMUSREKX-LMLFDSFASA-N

反应信息

• 作为反应物：
  描述：

  methyl 2-O-(tert-butyldimethylsilyl)-β-D-xylofuranoside 在 吡啶 、 二甲基二环氧乙烷 、 三氟乙酸酐 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 15.5h， 生成 methyl 2,5-bis-O-(tert-butyldimethylsilyl)-4-C-methyl-α-L-arabinofuranoside
  参考文献：
  名称：

  Anti versus Syn Opening of Epoxides Derived from 9-(3-Deoxy-β-d-glycero-pent-3-enofuranosyl)adenine with Me₃Al:  Factors Controlling the Stereoselectivity

  摘要：

  [graphics]Upon epoxidation with dimethyldioxirane, the 2',5'-bis-O-silyl derivatives of 9-(3-deoXy-beta-D-glyceropent-3-enofuranosyl)adenine gave the respective "3',4'-up" epoxides exclusively. Reaction between these epoxides and Me3Al was investigated in detail. It was found that the stereoselectivity of epoxide ring opening (anti versus syn) varied significantly upon changing the amount of Me3Al, the solvent, the O-silyl protecting group, and the reaction temperature. A possible reaction mechanism is proposed.

  DOI：

  10.1021/jo052243l
• 作为产物：
  描述：

  methyl 3,5-di-O-benzoyl-2-O-(tert-butyldimethylsilyl)-β-D-xylofuranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以98%的产率得到methyl 2-O-(tert-butyldimethylsilyl)-β-D-xylofuranoside
  参考文献：
  名称：

  Anti versus Syn Opening of Epoxides Derived from 9-(3-Deoxy-β-d-glycero-pent-3-enofuranosyl)adenine with Me₃Al:  Factors Controlling the Stereoselectivity

  摘要：

  [graphics]Upon epoxidation with dimethyldioxirane, the 2',5'-bis-O-silyl derivatives of 9-(3-deoXy-beta-D-glyceropent-3-enofuranosyl)adenine gave the respective "3',4'-up" epoxides exclusively. Reaction between these epoxides and Me3Al was investigated in detail. It was found that the stereoselectivity of epoxide ring opening (anti versus syn) varied significantly upon changing the amount of Me3Al, the solvent, the O-silyl protecting group, and the reaction temperature. A possible reaction mechanism is proposed.

  DOI：

  10.1021/jo052243l