(3R,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-4-((2S,3R,5S)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-butyric acid | 204004-38-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3R,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-4-((2S,3R,5S)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-butyric acid
• 英文别名: (3R,4R)-3-[tert-butyl(dimethyl)silyl]oxy-4-methoxy-4-[(2S,3R,5S)-5-methoxy-3-methyloxolan-2-yl]butanoic acid
• CAS: 204004-38-6
• 化学式: C₁₇H₃₄O₆Si
• 分子量: 362.539
• InChiKey: XLVDJMWPXVMXMC-WOOFSFRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3R,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-4-((2S,3R,5S)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-butyric acid 在 chromium dichloride 、 4-二甲氨基吡啶 、 2,4,6-三氯苯甲酰氯 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 nickel dichloride 作用下， 以 四氢呋喃 、 二甲基亚砜 、 甲苯 、 苯 为溶剂， 反应 19.0h， 生成 (3R,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-4-((2S,3R,5S)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-butyric acid (3E,5E)-(R)-1,8-dimethyl-7-oxo-nona-3,5-dienyl ester
  参考文献：
  名称：

  Toward a total synthesis of an aglycone of spiramycin; preparation of a C-10/C-15 fragment

  摘要：

  Esters of the dienyl iodide 2a, which was obtained stereoselectively from the corresponding tin derivative 2b, were shown to condense with i-butyraldehyde in the conditions of the Kishi-Nozaki-Takai reaction without alteration of the E,E configuration of the butadiene moiety. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)83164-4
• 作为产物：
  描述：

  (3R,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-4-((2S,3R,5S)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-butyraldehyde 在 potassium permanganate 、 potassium dihydrogenphosphate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 0.25h， 以87%的产率得到(3R,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-4-((2S,3R,5S)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-butyric acid
  参考文献：
  名称：

  Toward a total synthesis of an aglycone of spiramycin; installation of the hydroxy groups at C-4 and C-5: a model study

  摘要：

  The stereochemical course of the osmium-mediated bis-hydroxylation of the allylic derivative 6c, whose the structure is closely related to that of a C-1/C-7 fragment of the title aglycone, has been established unambiguously by X-ray analysis of a carboxylic acid derived from one of the two diastereomeric dials which formed. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10760-2

文献信息

• Toward a total synthesis of an aglycone of spiramycin; installation of the hydroxy groups at C-4 and C-5: a model study
  作者：G Oddon、D Uguen、A De Cian、J Fischer

  DOI：10.1016/s0040-4039(97)10760-2

  日期：1998.3

  The stereochemical course of the osmium-mediated bis-hydroxylation of the allylic derivative 6c, whose the structure is closely related to that of a C-1/C-7 fragment of the title aglycone, has been established unambiguously by X-ray analysis of a carboxylic acid derived from one of the two diastereomeric dials which formed. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
• Toward a total synthesis of an aglycone of spiramycin; preparation of a C-10/C-15 fragment
  作者：G. Oddon、D. Uguen

  DOI：10.1016/s0040-4039(97)83164-4

  日期：1998.3

  Esters of the dienyl iodide 2a, which was obtained stereoselectively from the corresponding tin derivative 2b, were shown to condense with i-butyraldehyde in the conditions of the Kishi-Nozaki-Takai reaction without alteration of the E,E configuration of the butadiene moiety. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.