(3R)-4-[(2S,3R,5R)-2-[(1R,2R)-2-[tert-butyl(dimethyl)silyl]oxy-1-methoxybut-3-enyl]-5-methoxyoxolan-3-yl]-1-dimethoxyphosphoryl-3-methylbutan-2-ol | 200621-35-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: (3R)-4-[(2S,3R,5R)-2-[(1R,2R)-2-[tert-butyl(dimethyl)silyl]oxy-1-methoxybut-3-enyl]-5-methoxyoxolan-3-yl]-1-dimethoxyphosphoryl-3-methylbutan-2-ol
• CAS: 200621-35-8
• 化学式: C₂₃H₄₇O₈PSi
• 分子量: 510.681
• InChiKey: OZEQQCMSHWYWRA-RZVFZJBNSA-N

物化性质

• 沸点：
  540.455±50.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.060±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.83
• 重原子数：
  33
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3R)-4-[(2S,3R,5R)-2-[(1R,2R)-2-[tert-butyl(dimethyl)silyl]oxy-1-methoxybut-3-enyl]-5-methoxyoxolan-3-yl]-1-dimethoxyphosphoryl-3-methylbutan-2-ol 在 potassium permanganate 、 potassium dihydrogenphosphate 、 dimethyl sulfide borane 、 hydroxide 、 双氧水 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 、 叔丁醇 为溶剂， 反应 10.5h， 生成 (3R,4R)-3-[tert-butyl(dimethyl)silyl]oxy-4-[(2S,3R,5R)-3-[(2R)-4-dimethoxyphosphoryl-2-methyl-3-oxobutyl]-5-methoxyoxolan-2-yl]-4-methoxybutanoic acid
  参考文献：
  名称：

  Preparation of the C1∼C10 fragment of carbonolide B. A relay approach to carbomycin B

  摘要：

  Reaction of methyl 2,3-anhydro-5,6-O-cyclohexylidene-beta-D-allofuranoside with 2-methyl-2-propenylmagnesium chloride selectively gave methyl 5,6-O-cyclohexylidene-3-deoxy-3-C-(2-methyl- 2-propenyl)-beta-D-glucofuranoside, which was convened into the C1 similar to C10 fragment of carbonolide B by a sequence of reactions involving hydroboration of the prochiral double bond, oxidative cleavage between C5-C6, and subsequent stereoselective three-carbon elongation at the C5 position. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10258-1
• 作为产物：
  描述：

  (2R,3R,4R,5S)-5-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]-2-methoxy-4-(2-methylprop-2-enyl)oxolan-3-ol 在 sodium periodate 、 tetrafluoroboric acid 、 偶氮二异丁腈 、 甲基锂 、 hydroxide 、 双氧水 、 三正丁基氢锡 、 sodium hydride 、 戴斯-马丁氧化剂 、 三乙胺 、 magnesium bromide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 苯 为溶剂， 反应 61.42h， 生成 (3R)-4-[(2S,3R,5R)-2-[(1R,2R)-2-[tert-butyl(dimethyl)silyl]oxy-1-methoxybut-3-enyl]-5-methoxyoxolan-3-yl]-1-dimethoxyphosphoryl-3-methylbutan-2-ol
  参考文献：
  名称：

  Preparation of the C1∼C10 fragment of carbonolide B. A relay approach to carbomycin B

  摘要：

  Reaction of methyl 2,3-anhydro-5,6-O-cyclohexylidene-beta-D-allofuranoside with 2-methyl-2-propenylmagnesium chloride selectively gave methyl 5,6-O-cyclohexylidene-3-deoxy-3-C-(2-methyl- 2-propenyl)-beta-D-glucofuranoside, which was convened into the C1 similar to C10 fragment of carbonolide B by a sequence of reactions involving hydroboration of the prochiral double bond, oxidative cleavage between C5-C6, and subsequent stereoselective three-carbon elongation at the C5 position. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10258-1

文献信息

• Preparation of the C1∼C10 fragment of carbonolide B. A relay approach to carbomycin B
  作者：Takaaki Shimura、Chiyoko Komatsu、Masakazu Matsumura、Yuzo Shimada、Kazuo Ohta、Oyo Mitsunobu

  DOI：10.1016/s0040-4039(97)10258-1

  日期：1997.12

  Reaction of methyl 2,3-anhydro-5,6-O-cyclohexylidene-beta-D-allofuranoside with 2-methyl-2-propenylmagnesium chloride selectively gave methyl 5,6-O-cyclohexylidene-3-deoxy-3-C-(2-methyl- 2-propenyl)-beta-D-glucofuranoside, which was convened into the C1 similar to C10 fragment of carbonolide B by a sequence of reactions involving hydroboration of the prochiral double bond, oxidative cleavage between C5-C6, and subsequent stereoselective three-carbon elongation at the C5 position. (C) 1997 Elsevier Science Ltd.