(2R,3R)-3-hydroxy-2-<(2,6-diisopropoxybenzoyl)oxy>butanedioic acid | 131703-53-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3R)-3-hydroxy-2-<(2,6-diisopropoxybenzoyl)oxy>butanedioic acid
• 英文别名: (2R,3R)-2-O-(2,6-diisopropoxybenzoyl) tartaric acid；(2R,3R)-2-O-(2,6-diisopropoxybenzoyl)tartaric acid；(2R,3R)-2-O-(2,6-diisopropoxybenzoyl) tartrate；(2R,3R)-2-[2,6-di(propan-2-yloxy)benzoyl]oxy-3-hydroxybutanedioic acid
• CAS: 131703-53-2
• 化学式: C₁₇H₂₂O₉
• 分子量: 370.356
• InChiKey: JIEYCPILVNXLJR-ZIAGYGMSSA-N

物化性质

• 沸点：
  575.5±50.0 °C(Predicted)
• 密度：
  1.326±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  140
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-hydroxy-2-<(2,6-diisopropoxybenzoyl)oxy>butanedioic acid 、 2,6-双(三氟甲基)苯硼酸 以 further solvent(s) 为溶剂， 生成
  参考文献：
  名称：

  Catalytic asymmetric allylation using a chiral (acyloxy)borane complex as a versatile Lewis acid catalyst

  摘要：

  In the presence of 20 mol % of a chiral (acyloxy)borane (CAB) complex prepared from (2R,3R)-2-O-(2,6-diisopropoxybenzoyl)tartaric acid and borane-tetrahydrofuran, various allyltrimethylsilanes react with achiral aldehydes to afford the corresponding homoallylic alcohols in good yields with high diastereo- and enantioselectivities. Furthermore, the reactivity of allylation can be improved without reducing the enantioselelctivity by using 10-20 mol % of the CAB complex prepared from 3,5-bis(trifluoromethyl)phenylboronic acid and chiral tartaric acid derivative. The observed selectivities and re-face attack of nucleophiles on the carbonyl carbons of aldehydes imply that the extended transition-state model is applicable.

  DOI：

  10.1021/ja00077a054
• 作为产物：
  描述：

  2,6-二羟基苯甲酸 在 palladium on activated charcoal 氢氧化钾 、 氢气 、 potassium carbonate 、 三氟乙酸酐 作用下， 以 甲醇 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 25.0~80.0 ℃ 、101.33 kPa 条件下， 反应 100.5h， 生成 (2R,3R)-3-hydroxy-2-<(2,6-diisopropoxybenzoyl)oxy>butanedioic acid
  参考文献：
  名称：

  稳定易制备的CAB催化剂催化不对称杂Diels-Alder反应

  摘要：

  通过在室温下混合酒石酸衍生物和芳基硼​​酸原位制备稳定的手性（酰氧基）硼烷（CAB）配合物。该催化剂的溶液有效地催化杂Diels-Alder反应以产生高光学纯度的二氢吡喃酮衍生物。

  DOI：

  10.1016/s0040-4020(01)80812-7
• 作为试剂：
  描述：

  反式肉桂醛 、 反-1-甲氧基-3-(三甲基硅氧基)-1,3-丁二烯 在 2-异丙氧基苯硼酸 、 (2R,3R)-3-hydroxy-2-<(2,6-diisopropoxybenzoyl)oxy>butanedioic acid 、 三氟乙酸 作用下， 生成 (S)-(+)-2-[(E)-styryl]-2,3-dihydro-4H-pyran-4-one 、 (R)-2-(E)-styryl-2,3-dihydro-4H-pyran-4-one
  参考文献：
  名称：

  稳定易制备的CAB催化剂催化不对称杂Diels-Alder反应

  摘要：

  通过在室温下混合酒石酸衍生物和芳基硼​​酸原位制备稳定的手性（酰氧基）硼烷（CAB）配合物。该催化剂的溶液有效地催化杂Diels-Alder反应以产生高光学纯度的二氢吡喃酮衍生物。

  DOI：

  10.1016/s0040-4020(01)80812-7

文献信息

• Catalytic Asymmetric Aldol-Type Reactions Using a Chiral (Acyloxy)borane Complex
  作者：Kazuaki Ishihara、Tohru Maruyama、Makoto Mouri、Qingzhi Gao、Kyoji Furuta、Hisashi Yamamoto

  DOI：10.1246/bcsj.66.3483

  日期：1993.11

  In the presence of 20 mol% of a chiral (acyloxy)borane (CAB) complex prepared from BH3·THF and a chiral mono-O-acylated tartaric acid, achiral silyl enol ethers or ketene silyl acetals react with achiral aldehydes to afford the corresponding aldol-type adducts in good yields with high enantio- and diastereoselectivities. Furthermore, the reactivity of aldol-type reactions can be improved without reducing

  在 20 mol% 的由 BH3·THF 和手性单-O-酰化酒石酸制备的手性（酰氧基）硼烷（CAB）配合物存在下，非手性甲硅烷基烯醇醚或烯酮甲硅烷基缩醛与非手性醛反应得到相应的醛醇型加合物产率高，对映选择性和非对映选择性高。此外，通过使用由3,5-双(三氟甲基)苯基硼酸和手性酒石酸衍生物制备的10-20mol%的CAB配合物，可以在不降低对映选择性的情况下提高羟醛型反应的反应性。通过使用由邻苯氧基苯基硼酸和手性酒石酸衍生物制备的 20 mol% 的 CAB 配合物，还可以在不降低化学产率的情况下提高对映选择性。
• Tartaric acid and its acyl derivatives. Part 5. Direct synthesis of monoacyltartaric acids and novel mono(benzoyl)tartaric anhydride: unusual findings in tartaric acid acylation
  作者：Urszula Bernaś、Halina Hajmowicz、Izabela D. Madura、Monika Majcher、Ludwik Synoradzki、Krzysztof Zawada

  DOI：10.3998/ark.5550190.0011.b01

  日期：——

  unprotected tartaric acid 1 by acyl chlorides to the corresponding monoacyltartaric acids 2 has been shown. Several unusual cases in the acylation of 1 are observed; it has been found that two routes of acylation are possible. In the benzoylation of 1, in addition to the expected products, the formation of a previously undescribed monobenzoyltartaric anhydride 7a is reported. An unusual DME cleavage

  未保护的酒石酸 1 被酰氯实际酰化为相应的单酰基酒石酸 2 已被证明。在 1 的酰化中观察到几个不寻常的情况；已经发现有两种酰化途径是可能的。在 1 的苯甲酰化中，除了预期的产物外，还报告了先前未描述的单苯甲酰酒石酸酐 7a 的形成。还观察到在酰化过程中不寻常的 DME 裂解。
• Use of 1,3-Dioxin-4-ones and Related Compounds in Synthesis. XLIV. Asymmetric Aldol Reaction of 4-Trimethylsiloxy-6-methylene-1,3-dioxines: Use of Tartaric Acid-Derived (Acyloxy)borane Complex as the Catalyst.
  作者：Masayuki SATO、Satoshi SUNAMI、Yoshiaki SUGITA、Chikara KANEKO

  DOI：10.1248/cpb.42.839

  日期：——

  A novel enantioselective synthesis of 1, 3-dioxin-4-ones having a 2-hydroxylated alkyl group at the 6-position has been accomplished by chiral tartaric acid-derived acylborane-mediated aldol condensation of the silyl enol ether derived from 6-methyl-derivatives of 1, 3-dioxin-4-one with achiral aldehydes.

  通过手性酒石酸衍生的酰基硼烷介导的源自 6-甲基的硅烯醇醚的醇醛缩合，完成了在 6 位具有 2-羟基化烷基的 1, 3-二恶英-4-酮的新型对映选择性合成-1, 3-二恶英-4-酮与非手性醛的衍生物。
• Asymmetric Allylation Polymerization of Bis(allylsilane) and Dialdehyde Containing Arylsilane Structure
  作者：Toshihiro Kumagai、Shinichi Itsuno

  DOI：10.1021/ma012023j

  日期：2002.6.1
• Asymmetric Polymer Synthesis by Repetitive SakuraiHosomi Allylation Reaction of Compounds Possessing Both Formyl and Allylsilane Functions
  作者：Shinichi Itsuno、Toshihiro Kumagai

  DOI：10.1002/1522-2675(200210)85:10<3185::aid-hlca3185>3.0.co;2-b

  日期：2002.10

  Trialkylallylsilanes generally react with aldehydes in the presence of a Lewis acid to the corresponding homoallylic alcohols. Chiral Lewis acids promote the same reaction to yield the enantiomerically-enriched homoallylalcohols. We have prepared four compounds (7-10) that possess both formyl and allylsilane functions. Lewis acids initiated self-polyaddition reactions of these compounds by means of repetitive allylation. The use of chiral Lewis acids resulted in the formation of optically active polymers that possess exo-methylene and secondary OH functions in their main chain. The optical purity of these chiral polymers was estimated based on the results of model asymmetric reactions between benzaldehyde and beta-substituted allylsilanes and by controlled degradation.