(2S,3S)-3,4-epoxy-1,2-di-O-isopropylidenebutane-1,2-diol | 93367-10-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S)-3,4-epoxy-1,2-di-O-isopropylidenebutane-1,2-diol
• 英文别名: (4S)-2,2-dimethyl-4-[(2S)-oxiran-2-yl]-1,3-dioxolane；(S)-2,2-dimethyl-4-((S)-oxiran-2-yl)-1,3-dioxolane；(2S,3S)-1,2-epoxy-3,4-isopropylidenedioxy-butane
• CAS: 93367-10-3
• 化学式: C₇H₁₂O₃
• 分子量: 144.17
• InChiKey: VFFXYLYACPOCSJ-WDSKDSINSA-N

物化性质

• 沸点：
  174.2±25.0 °C(Predicted)
• 密度：
  1.133±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：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  31
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3,4-epoxy-1,2-di-O-isopropylidenebutane-1,2-diol 在 sodium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 双氧水 、 三苯基膦 作用下， 反应 48.25h， 生成 (R)-4-(2-羟乙基)-2,2-二甲基-1,3-二氧戊环
  参考文献：
  名称：

  Saibaba, Rasha; Sarma, Mallela S. P.; Abushanab, Elie, Synthetic Communications, 1989, vol. 19, # 17, p. 3077 - 3086

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl (2R)-2-[(1S)-3,3-dimethyl(2,4-dioxolanyl)]-2-hydroxyacetate 在 lithium aluminium tetrahydride 、 TEA 、 对甲苯磺酰氯 作用下， 生成 (2S,3S)-3,4-epoxy-1,2-di-O-isopropylidenebutane-1,2-diol
  参考文献：
  名称：

  Synthesis of the C₁−C₁₂ Fragment of the Tedanolides. Aldol−Non-Aldol Aldol Approach

  摘要：

  The combination of highly stereoselective non-aldol aldol and aldol processes allows the preparation of the completely protected C-1-C-12 fragment 2 of the novel macrocyclic cytotoxic agent tedanolide 1.

  DOI：

  10.1021/ol0714038

文献信息

• Formal total synthesis of aspergillides A and B
  作者：Gangavaram V.M. Sharma、Vennampalli Manohar

  DOI：10.1016/j.tetasy.2012.02.009

  日期：2012.2

  The formal total synthesis of the cytotoxic 14-membered macrolides, aspergillides A and B is described. A combination of a chiron approach and an asymmetric synthesis is adopted for the synthesis of the target macrolides. The required 2,6-syn and 2,6-anti tetrahydropyrans were constructed via a tandem Sharpless asymmetric epoxidation and 6-exo cyclization on δ-hydroxy allylic alcohols, as the key steps

  描述了细胞毒性的14元大环内酯类，曲霉内酯A和B的正式全合成。将Chiron方法和不对称合成的组合用于目标大环内酯的合成。通过串联的Sharpless不对称环氧化和在δ-羟基烯丙醇上的6- exo环化反应来构建所需的2,6- syn和2,6-抗四氢吡喃，这是关键步骤。必需的手性合成子是由1-抗坏血酸制备的。
• Practical enantiospecific syntheses of (+) erythro-9- (2s-hydroxy-3r-nonyl) adenine.
  作者：Elie Abushanab、Michel Bessodes、Kostas Antonakis

  DOI：10.1016/s0040-4039(01)91182-7

  日期：1984.1

  Three enantiospecific syntheses of 1S (2S-benzyloxethyl) oxirane (9) from L-ascorbic acid, L(+) tartaric acid, and Z-butene 1,4-diol are reported. The conversion of 9 to 2S-hydroxy-3R-nonylamine (19) is also described.

  报道了从L-抗坏血酸，L（+）酒石酸和Z-丁烯1,4-二醇合成1S（2S-苄氧基乙基）环氧乙烷（9）的三种对映体特异性化合物。还描述了从9到2S-羟基-3R-壬胺的转化（19）。
• A convenient approach to total synthesis of synargentolide-B from l-ascorbic acid and d-ribose
  作者：Saidulu Konda、K. Bhaskar、Lingaiah Nagarapu、Dattatray M. Akkewar

  DOI：10.1016/j.tetlet.2014.03.133

  日期：2014.5

  A convenient and practical approach for the total synthesis of naturally occurring lactone synargentolide-B has been accomplished in 14 steps from the commercially available l-ascorbic acid and d-ribose involving Bestmann–Ohira reaction, zinc mediated allylation, ring closing-metathesis, and cross-metathesis reactions. The highlight of our strategy describes a one-pot reaction involving stereoselective

  对于天然存在的内酯synargentolide-B已经在14个步骤由市售完成了全合成的方便和实用的方法升抗坏血酸和ð核糖涉及Bestmann-大平反应，锌介导的烯丙基化，环闭合复分解反应，并跨复分解反应。我们策略的重点是描述一锅反应，包括立体选择性添加烯丙基锌试剂和选择性还原末端炔烃以获得关键的高级中间体。
• Total Synthesis of Anticancer Agent EBC-23
  作者：Dodda Vasudeva Reddy、Gowravaram Sabitha、Tadikamalla Prabhakar Rao、Jhillu Singh Yadav

  DOI：10.1021/acs.orglett.6b01849

  日期：2016.9.2

  Total synthesis of spiroketal EBC-23 has been described by two divergent approaches from three simple building blocks. Gold-catalyzed cycloisomerization of alkynol and acid-mediated spirocyclization of diketalketone were successfully utilized to effect spiroketal formation. A Cu(I)–P(Cy)3-catalyzed protocol for the highly regio- and stereocontrolled hydroboration of internal propargylic alcohol was

  螺旋体EBC-23的总合成已通过三种简单的构建基块中的两种不同方法进行了描述。金催化炔醇的环异构化和酸介导的二酮内酯的螺环化已成功地用于影响螺环的形成。Cu（I）–P（Cy）3催化的内部炔丙醇的高度区域控制和立体控制的硼氢化反应协议已通过乙烯基硼酸酯有效地应用于β-羟基酮。
• First stereoselective total synthesis of panaxjapyne C
  作者：Pallavi Thakur、B. Kumaraswamy、G. Raji Reddy、Rakeshwar Bandichhor、K. Mukkanti

  DOI：10.1016/j.tetlet.2012.04.087

  日期：2012.7

  The first stereoselective total synthesis of polyacetylene panaxjapyne C is described. The key reactions include regioselective opening of the epoxide and Cadiot–Chodkiewicz cross-coupling reactions. l-Ascorbic acid was used as a chiral pool material for the construction of the both terminal acetylenes.

  描述了聚乙炔人参ja啶C的第一立体选择性全合成。关键反应包括环氧化物的区域选择性开放和Cadiot-Chodkiewicz交叉偶联反应。1-抗坏血酸用作两个末端乙炔的手性池材料。