(4S,5R)-2,2,5-trimethyl-1,3-dioxolane-4-methanol | 111319-77-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,5R)-2,2,5-trimethyl-1,3-dioxolane-4-methanol
• 英文别名: (2S,3R)-2,3-(propane-2,2-dioxy)-1-butanol；[(4S,5R)-2,2,5-trimethyl-1,3-dioxolan-4-yl]methanol
• CAS: 111319-77-8
• 化学式: C₇H₁₄O₃
• 分子量: 146.186
• InChiKey: VWUQFWPEGNZUQV-RITPCOANSA-N

物化性质

• 沸点：
  192.1±15.0 °C(Predicted)
• 密度：
  0.989±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S,5R)-2,2,5-trimethyl-1,3-dioxolane-4-methanol 在 正丁基锂 、 草酰氯 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (6S,7S)-6,7-(propane-2,2-dioxy)-5-hydroxyocta-2-en-4-lactone
  参考文献：
  名称：

  Versicolactones A and B: total synthesis and structure revision

  摘要：

  To further determine absolute configurations of versicolactones A and B, total synthesis of versicolactones A and B and their six stereoisomers were reported in this Letter. The H-1 and C-13 NMR spectra of the synthetic erythro-stereoisomers matched perfectly with those of the natural products. Combined with the comparison of the specific rotations, the absolute configuration of versicolactones A and B were revised as (4Z,6R,7S)- and (4E,6R,7S)- from the corresponding (4Z,6R,7R)- and (4E,6R,7R)-6,7-dihydroxyocta-2,4-dien-4-lactone, respectively. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.120
• 作为产物：
  描述：

  (2S,3R,4S,5S)-2,3-(propane-2,2-dioxy)hexane-1,4,5-triol 在 咪唑 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 sodium periodate 、 lithium aluminium tetrahydride 、 四丁基氟化铵 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 20.33h， 生成 (4S,5R)-2,2,5-trimethyl-1,3-dioxolane-4-methanol
  参考文献：
  名称：

  Versicolactones A and B: total synthesis and structure revision

  摘要：

  To further determine absolute configurations of versicolactones A and B, total synthesis of versicolactones A and B and their six stereoisomers were reported in this Letter. The H-1 and C-13 NMR spectra of the synthetic erythro-stereoisomers matched perfectly with those of the natural products. Combined with the comparison of the specific rotations, the absolute configuration of versicolactones A and B were revised as (4Z,6R,7S)- and (4E,6R,7S)- from the corresponding (4Z,6R,7R)- and (4E,6R,7R)-6,7-dihydroxyocta-2,4-dien-4-lactone, respectively. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.120

文献信息

• Enzymatic enantioselective hydrolysis of 2,2-dimethyl-1,3-dioxolane-4-carboxylic esters
  作者：M. Pottie、J. Van der Eycken、M. Vandewalle、J.M. Dewanckele、H. Röper

  DOI：10.1016/s0040-4039(01)93775-x

  日期：1989.1

  2,2-Dimethyl-1,3-dioxolane-4-carboxylic acid derived chiral building blocks were prepared from substituted α,β-unsaturated acids with high enantiomeric purities by enzymatic hydrolysis of their n.butyl esters.

  2，2-二甲基-1，3-二氧戊环-4-羧酸衍生的手性结构单元是由具有高对映体纯度的取代的α，β-不饱和酸通过其正丁酯的酶促水解制备的。
• Asymmetric Dihydroxylations of ?-SubstitutedN-(?,?-Enoyl)bornane-10,2-sultams
  作者：Wolfgang Oppolzer、Jean-Pierre Barras

  DOI：10.1002/hlca.19870700703

  日期：1987.11.4

  Pure (E)- or (Z)-enoylsultams 2 were Oxidized with OsO4/N-Methylmorpholine N-oxide in a stereospecific and highly π-face-selective manner. Acetalization of the resulting 1,2-diols furnished, after purification, the stable, crystalline acetals 6 in >99% d.e. and in 63–74% overall yield from 2. Reductive or hydrolytic cleavage of 6 gave enantiomerically pure alcohols 8 or carboxylic acids 9 with recovery

  用OsO 4 / N-甲基吗啉N-氧化物以立体有择且高度π面选择性的方式将纯净的（E）-或（Z）-烯酰基阿磺酰胺2氧化。纯化后得到的1,2-二醇的缩醛化反应提供了稳定的结晶乙缩醛6，其> 99％de的产率为63-74％，总产率为2。6的还原或水解裂解得到对映体纯的醇8或羧酸9，同时回收了苏丹助剂1。
• Synthesis of alditols by reductive radical fragmentation of N-phthalimido glycosides. Preparation of chiral synthetic intermediates
  作者：Angeles Martín、María S. Rodríguez、Ernesto Suárez

  DOI：10.1016/s0040-4039(99)01482-3

  日期：1999.10

  The reaction of N-phthalimido glycofuranosides and glycopyranosides with produces radical β-fragmentation of the carbohydrate C1C2 bond through the formation of anomeric alkoxy radicals. This constitutes a new two-step methodology for the facile conversion of carbohydrates into the corresponding acyclic alditols with one fewer carbon.

  的反应Ñ -phthalimido glycofuranosides并用glycopyranosides通过异头烷氧基自由基的形成产生碳水化合物C1C2键的自由基β-碎片。这构成了一种新的两步法，可轻松地将碳水化合物转化为碳含量低的相应无环醛糖醇。
• OPPOLZER, WOLFGANG;BARRAS, JEAN-PIERRE, HELV. CHIM. ACTA, 70,(1987) N 7, 1666-1675
  作者：OPPOLZER, WOLFGANG、BARRAS, JEAN-PIERRE

  DOI：——

  日期：——
• FUGANTI C.; GRASSELLI P.; SERVI S.; LAZZARINI A.; CASATI P., J. CHEM. SOC. CHEM. COMMUN.,(1987) N 8, 538-539
  作者：FUGANTI C.、 GRASSELLI P.、 SERVI S.、 LAZZARINI A.、 CASATI P.

  DOI：——

  日期：——