(4S,5S)-(-)-2,2,N,N,N',N'-hexamethyl-1,3-dioxolane-4,5-dicarboxamide | 111828-49-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,5S)-(-)-2,2,N,N,N',N'-hexamethyl-1,3-dioxolane-4,5-dicarboxamide
• 英文别名: (4S,5S)-4-N,4-N,5-N,5-N,2,2-hexamethyl-1,3-dioxolane-4,5-dicarboxamide
• CAS: 111828-49-0
• 化学式: C₁₁H₂₀N₂O₄
• 分子量: 244.291
• InChiKey: VCLVBIPTRZNCGF-YUMQZZPRSA-N

物化性质

• 沸点：
  380.6±42.0 °C(Predicted)
• 密度：
  1.114±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,5S)-(-)-2,2,N,N,N',N'-hexamethyl-1,3-dioxolane-4,5-dicarboxamide 生成 (4R,5R,1'S)-4,5-bis-(1'-hydroxyhex-1'-yl)-2,2-dimethyl-1,3-dioxolane
  参考文献：
  名称：

  酒石酸的转化：旋光性α-氢醛衍生物的简便合成

  摘要：

  描述了由旋光性酒石酸合成（）-和（）-2-苄氧基-和2-（叔丁基二苯基甲硅烷氧基）-醛的方法。

  DOI：

  10.1016/s0040-4039(00)96267-1
• 作为产物：
  描述：

  D-酒石酸 生成 (4S,5S)-(-)-2,2,N,N,N',N'-hexamethyl-1,3-dioxolane-4,5-dicarboxamide
  参考文献：
  名称：

  酒石酸的转化：旋光性α-氢醛衍生物的简便合成

  摘要：

  描述了由旋光性酒石酸合成（）-和（）-2-苄氧基-和2-（叔丁基二苯基甲硅烷氧基）-醛的方法。

  DOI：

  10.1016/s0040-4039(00)96267-1

文献信息

• Preparation and Structural Analysis of Several New α,α,α′,α′-Tetraaryl-1,3-dioxolane-4,5-dimethanols (TADDOL's) and TADDOL analogs, their evaluation as titanium ligands in the enantioselective addition of methyltitanium and diethylzinc reagents to benzald
  作者：Yoshio N. Ito、Xavier Ariza、Albert K. Beck、Andrej Boháč、Camille Ganter、Robert E. Gawley、Florian N. M. Kühnle、Juraj Tuleja、Yan Ming Wang、Dieter Seebach

  DOI：10.1002/hlca.19940770802

  日期：1994.12.14

  Preparation and screening of twenty new ligands, all analogs of α,α,α′,α′-tetraaryl-1,3-dioxolane-4,5-dimethanol (TADDOL), for the Ti-catalyzed asymmetric addition of methyltri(isopropoxy)titanium and diethylzinc to benzaldehyde are described. These ligands have the dioxolane ring of the TADDOL's replaced by cyclobutane, cyclopentane, cyclohexene, cyclohexane, bicyclo[2.2.1]heptene and -heptane and

  Ti催化不对称加成甲基三（异丙氧基）的二十种新配体的制备和筛选，这些配体是α，α，α'，α'-四芳基-1,3-二氧戊环-4,5-二甲醇（TADDOL）的所有类似物描述了钛和二乙基锌与苯甲醛。这些配体具有被环丁烷，环戊烷，环己烯，环己烷，双环[2.2.1]庚烯和-庚烷以及双环[2.2.2]辛烯和-辛烷部分取代的TADDOL的二氧戊环。一些具有取代芳基的H原子或烷基，并且其中九个具有C 2对称性。X射线晶体学和分子力学用于分析配体的结构，并且两个结构特征似乎与选择性相关：（i）螯合O原子和邻位原子的扭转角轴向Ph族的-C原子（小，约19°，最佳角度，图8），以及（ii）轴向Ph族的“垂直度”（图9）。竞争实验表明，TADDOL 1a催化甲基钛和二乙基锌的添加速度比相关的二氧戊环类似物12a，12c和12e快50倍以上（方案7），表明配体需要轴向和赤道芳基（见脚注6）这些反应的加速催化。提出了完
• Stereoselective total syntheses of (−)-hygrophorone A¹², 4-<i>O</i>-acetyl-hygrophorone A¹² and (+)-hygrophorone B¹²
  作者：Sayani Das、Anu Dalal、Shivajirao L. Gholap

  DOI：10.1039/d0ob02303e

  日期：——

  Total syntheses of anti-fungal cyclopentenones (−)-hygrophorone A12, 4-O-acetyl-hygrophorone A12 and (+)-hygrophorone B12 were achieved in high overall yields from D-(−)-tartaric acid. The key feature of these syntheses is the aqueous KOH-mediated diastereoselective intramolecular aldol reaction to form β-hydroxy ketone with three contiguous chiral centres, which was further elaborated to (−)-hygrophorone

  抗真菌环戊烯酮的全合成（ - ） - hygrophorone甲12，4- ø -乙酰基hygrophorone甲12和（+） - hygrophorone乙12是在高的总产率从取得d - （ - ） -酒石酸。这些合成的关键特征是水性KOH介导的非对映选择性分子内醇醛羟醛反应，形成具有三个连续手性中心的β-羟基酮，并将其进一步精制为（-）-大佛尔酮A 12和（+）-大佛尔酮B 12。此处报道的合成路线操作简单且非对映选择性高，适合合成潮氧佛酮的几种类似物。
• Intermediates for preparating non-peptide retroviral protease inhibitors
  申请人：ABBOTT LABORATORIES

  公开号：EP0839798A2

  公开（公告）日：1998-05-06

  Intermediates, for preparing non-peptide retroviral protease inhibitors, said intermediates having the formula: or an acid addition salt thereof or an N-protected derivative thereof wherein at each occurrence the N-protecting group is independently selected from the group consisting of formyl, acetyl, pivaloyl, t-butylacetyl, t-butyloxycarbonyl, benzyloxycarbonyl, benzyl and isopropylaminocarbonyl; or said intermediates being selected from: (2S,3R,4S,5S)-2,5-di-(N-(Cbz-valinyl)amino)-3,4-dihydroxy-1,6-diphenylhexane; (2S,3S,4S,5S)-2,5-di-(N-(Cbz-valinyl)amino)-3,4-dihydroxy-1,6-diphenylhexane; (2S,3R,4R,5S)-2,5-di-(N-(Cbz-valinyl)amino)-3,4-dihydroxy-1,6-diphenylhexane; (2S,3S,4S,5S)-2,5-di-(N-(valinyl)amino)-3,4-dihydroxy-1,6-diphenylhexane; (2S,3R,4S,5S)-2,5-di-(N-(valinyl)amino)-3,4-dihydroxy-1,6-diphenylhexane; (2S,3R,4R,5S)-2,5-di-(N-(valinyl)amino)-3,4-dihydroxy-1,6-diphenylhexane; (2S,3S,4R,5S)-2-(N-(t-butyloxy)carbonyl)amino)-5-(N-(Cbz-valinyl)amino)-3,4-dihydroxy-1,6-diphenylhexane; 2-(N-benzyl-N-(benzyloxycarbonyl)amino)-5-(t-butyloxycarbonylamino)-1,6-diphenyl-3-hexene-3,4-oxide; 2-amino-5-(t-butyloxycarbonylamino)-1,6-diphenyl-3-hexene-3,4-oxide; and 2,5-di-(t-butyloxycarbonylamino)-1,6-diphenyl-3-hexene-3,4-oxide; or an acid addition salt thereof.

  用于制备非肽类逆转录病毒蛋白酶抑制剂的中间体，所述中间体具有以下式子： 或其酸加成盐或其 N-保护衍生物，其中每次出现时，N-保护基独立选自甲酰、乙酰、特戊酰、叔丁基乙酰、叔丁氧羰基、苄氧羰基、苄基和异丙氨基羰基组成的组；或所述中间体选自以下物质 (2S,3R,4S,5S)-2,5-二(N-(Cbz-缬氨酰)氨基)-3,4-二羟基-1,6-二苯基己烷； (2S,3S,4S,5S)-2,5-二(N-苄氧羰基缬氨酰氨基)-3,4-二羟基-1,6-二苯基己烷； (2S,3R,4R,5S)-2,5-二(N-苄氧羰基缬氨酰氨基)-3,4-二羟基-1,6-二苯基己烷； (2S,3S,4S,5S)-2,5-二(N-(缬氨酰)氨基)-3,4-二羟基-1,6-二苯基己烷； (2S,3R,4S,5S)-2,5-二(N-(缬氨酰)氨基)-3,4-二羟基-1,6-二苯基己烷； (2S,3R,4R,5S)-2,5-二(N-(缬氨酰)氨基)-3,4-二羟基-1,6-二苯基己烷； (2S,3S,4R,5S)-2-(N-(叔丁氧基)羰基)氨基)-5-(N-(Cbz-缬氨酰)氨基)-3,4-二羟基-1,6-二苯基己烷； 2-(N-苄基-N-(苄氧羰基)氨基)-5-(叔丁氧羰基氨基)-1,6-二苯基-3-己烯-3,4-氧化物； 2-氨基-5-(叔丁氧羰基氨基)-1,6-二苯基-3-己烯-3,4-氧化物；以及 2,5-二（叔丁氧羰基氨基）-1,6-二苯基-3-己烯-3,4-氧化物； 或其酸加成盐。
• Stereoselective Synthesis of (+)-Goniothalesdiol
  作者：Kavirayani R. Prasad、Shivajirao L. Gholap

  DOI：10.1021/jo060159f

  日期：2006.4.1

  Stereoselective synthesis of antitumor tetrahydrofuran (+)-goniothalesdiol was achieved in high overall yield from (-)-D-tartaric acid. Key features include an FeCl3 mediated THF formation with very high selectivity. Synthesis of natural gonithalesdiol and its analogue 2,5-bis-epi-goniothalesdiol was achieved from a common intermediate.
• Stereoselective Total Synthesis of Bioactive Styryllactones (+)-Goniofufurone, (+)7-<i>epi</i>-Goniofufurone, (+)-Goniopypyrone, (+)-Goniotriol, (+)-Altholactone, and (−)-Etharvensin
  作者：Kavirayani R. Prasad、Shivajirao L. Gholap

  DOI：10.1021/jo0702342

  日期：2008.1.1

  [GRAPHICS]Stereoselective total synthesis of biologically active styryllactones 7-epi-goniofufurone, goniofufurone, goniopypyrone, goniotriol, altholactone, and etharvensin was achieved in high overall yields from a common intermediate derived from D-(-)-tartaric acid. It is based on the utility of a masked tetrol, comprising an alkene tether and four contiguous hydroxy groups. The pivotal reaction sequence involves hydroxy-directed lactonization via the oxidation of alkene, and subsequent elaboration to styryllactones. The masked tetrol was prepared by the extension of gamma-phenyl-gamma-hydroxy butyramide, readily obtained from the bis-dimethylamide of tartaric acid, employing a combination of selective Grignard additions and a stereoselective reduction.