(3S,4R,5S)-4-Bromo-5-(tert-butyl-dimethyl-silanyloxymethyl)-3,5-dimethyl-dihydro-furan-2-one | 321907-63-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3S,4R,5S)-4-Bromo-5-(tert-butyl-dimethyl-silanyloxymethyl)-3,5-dimethyl-dihydro-furan-2-one
• 英文别名: (3S,4R,5S)-4-bromo-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-3,5-dimethyloxolan-2-one
• CAS: 321907-63-5
• 化学式: C₁₃H₂₅BrO₃Si
• 分子量: 337.329
• InChiKey: JBSDAWQOGLPACA-BREBYQMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,4R,5S)-4-Bromo-5-(tert-butyl-dimethyl-silanyloxymethyl)-3,5-dimethyl-dihydro-furan-2-one 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 L-(+)-酒石酸二异丙酯 、 二异丁基氢化铝 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 生成 [(2S,3R)-3-((2S,3R,4S,5R)-3-Bromo-5-methoxy-2,4-dimethyl-tetrahydro-furan-2-yl)-2-methyl-oxiranylmethoxy]-tert-butyl-dimethyl-silane
  参考文献：
  名称：

  Use of the non-aldol aldol process in the synthesis of the C1–C11 fragment of the tedanolides: use of lactol ethers in place of tetrahydrofurans

  摘要：

  The use of a lactol methyl ether 23 in place of the simple tetrahydrofuran 11 allows for the high yielding non-aldol aldol process to occur without concomitant tetrahydropyran formation (cf 13) to give the desired product 24 in good yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01726-3
• 作为产物：
  描述：

  ((2S,3R,4S)-3-Bromo-2,4-dimethyl-tetrahydro-furan-2-ylmethoxy)-tert-butyl-dimethyl-silane 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 、 乙腈 为溶剂， 以70%的产率得到(3S,4R,5S)-4-Bromo-5-(tert-butyl-dimethyl-silanyloxymethyl)-3,5-dimethyl-dihydro-furan-2-one
  参考文献：
  名称：

  Use of the non-aldol aldol process in the synthesis of the C1–C11 fragment of the tedanolides: use of lactol ethers in place of tetrahydrofurans

  摘要：

  The use of a lactol methyl ether 23 in place of the simple tetrahydrofuran 11 allows for the high yielding non-aldol aldol process to occur without concomitant tetrahydropyran formation (cf 13) to give the desired product 24 in good yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01726-3

文献信息

• Use of the non-aldol aldol process in the synthesis of the C1–C11 fragment of the tedanolides: use of lactol ethers in place of tetrahydrofurans
  作者：Michael E Jung、Christopher P Lee

  DOI：10.1016/s0040-4039(00)01726-3

  日期：2000.12

  The use of a lactol methyl ether 23 in place of the simple tetrahydrofuran 11 allows for the high yielding non-aldol aldol process to occur without concomitant tetrahydropyran formation (cf 13) to give the desired product 24 in good yield. (C) 2000 Elsevier Science Ltd. All rights reserved.