(1α,2α,3α,4β,5β)-pentahydroxycyclohexane | 78148-00-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1α,2α,3α,4β,5β)-pentahydroxycyclohexane
• 英文别名: (+)-1-deoxy-allo-inositol；3-deoxy-neo-inositol；(+)-talo-quercitol；(1S)-cyclohexane-1r,2c,3,4t,5t-pentaol；2D-1-deoxy-allo-inositol；(S)-Cyclohexan-1r,2c,3,4t,5t-pentaol；(1S,2S,4S,5S)-cyclohexane-1,2,3,4,5-pentol
• CAS: 78148-00-2
• 化学式: C₆H₁₂O₅
• 分子量: 164.158
• InChiKey: IMPKVMRTXBRHRB-FCAWWPLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  101
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1α,2α,3α,4β,5β)-pentahydroxycyclohexane 、 乙酸酐 在 吡啶 作用下， 反应 8.0h， 以90%的产率得到(1α,2α,3α,4β,5β)-pentaacetoxycyclohexane
  参考文献：
  名称：

  通过衍生自碳水化合物的对映体纯的炔烃系链的醛的自由基环异构化，不对称合成（+）-allo-quercitol和（+）-tal-quercitol。

  摘要：

  我们首次描述了从碳水化合物中获得的对映体纯的炔烃系醛的自由基环化反应（6、7）。报道了由D-核糖的衍生物获得的化合物6和7的合成。这些自由基前体已被氢化三丁基锡加偶氮二异丁腈进行环化，在闭环后分别产生两个碳环。这些碳环已作为E和Z乙烯基锡异构体的混合物获得，但在闭环过程中形成的新立体中心具有出色的非对映选择性。原甲酸酯化后，仅检测到并分离出一种非对映异构体。通过详细的（1）H NMR分析，可以确定在碳环化过程中形成的新立体中心的绝对构型。7-甲氧基甲氧基-2的具体转化，2-二甲基-4-亚甲基-5-叔丁基二甲基甲硅烷基氧基-（3aR，5S，7S，7aS）-全氢苯并[d] [1,3]二恶唑成光学纯的（+）-allo-槲皮醇和（+）-talo描述了-槲皮醇。从这些结果，我们得出结论，在激进的前体和条件的适当选择，生物兴趣的高功能环己烷衍生物的合成现已推出。

  DOI：

  10.1021/jo010455m
• 作为产物：
  描述：

  (1R,3R,7S,9S)-5,5,11,11-tetramethyl-4,6,10,12-tetraoxatricyclo[7.3.0.03,7]dodecan-2-ol 在 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 (1α,2α,3α,4β,5β)-pentahydroxycyclohexane
  参考文献：
  名称：

  Desymmetrization of Cyclohexadienylsilanes. Regio-, Diastereo-, and Enantioselective Access to Sugar Mimics

  摘要：

  Desymmetrization of cyclohexadienylsilanes available from Birch reduction of the corresponding arylsilanes is efficiently carried out using Sharpless asymmetric dihydroxylation and aminohydroxylation. Complete diastereocontrol and reasonable enantiocontrol have been attained during the preparation of the desired diols. An excellent regiocontrol has also been observed during aminohydroxylation of dienylsilanol 6b. The resulting diol 8 and hydroxycarbamate 27 have then been elaborated further, offering a straightforward access to various types of cyclitols, aminocyclitols, carbasugars, as well as the antibiotic palitantine 4. The complete functionalization of the original arylsilanes 5 is thus typically achieved in fewer than eight steps with high stereoselectivities and excellent overall yield.

  DOI：

  10.1021/jo991225z

文献信息

• A unified and common intermediate strategy for the asymmetric total synthesis of 3-deoxy-neo-inositol and conduritol E
  作者：Amarendra Panda、Rayhan Gafur Biswas、Shantanu Pal

  DOI：10.1016/j.tetlet.2016.06.127

  日期：2016.8

  3-deoxy-neo-inositol and conduritol E starting from d-ribose via a common chiral cyclohexenol derivative. The focal attributes of the synthetic route include stereoselective Grignard reaction, Wittig olefination, ring closing metathesis (RCM), and cis dihydroxylation.

  对于对映体纯的3-脱氧-新肌醇和conduritol E，从d-核糖开始，通过常见的手性环己烯醇衍生物，已经概述了一种有效，简单且统一的合成方法。合成路线的重点属性包括立体选择性格氏反应，Wittig烯烃化，闭环复分解（RCM）和顺式二羟基化。
• Carbohydrate Carbocyclization by a Novel Zinc-Mediated Domino Reaction and Ring-Closing Olefin Metathesis
  作者：Lene Hyldtoft、Robert Madsen

  DOI：10.1021/ja001415n

  日期：2000.9.1

  is described using two consecutive organometallic transformations: a novel zinc-mediated domino reaction to give functionalized dienes followed by ring-closing olefin metathesis. In the first reaction, methyl ω-deoxy-ω-iodo glycosides undergo reductive elimination with zinc to produce a terminal double bond. This also liberates the aldehyde which is immediately alkylated in situ by various organozinc

  使用两个连续的有机金属转化描述了碳水化合物碳环化的一般方法：一种新型的锌介导的多米诺反应，产生官能化的二烯，然后是闭环烯烃复分解。在第一个反应中，甲基ω-脱氧-ω-碘糖苷与锌进行还原消除以产生末端双键。这也释放出醛，该醛立即被各种有机锌试剂原位烷基化。在巴比耶条件下，用亚甲基碘和几种烯丙基溴进行烷基化。锌通过促进还原消除和激活烷基卤而发挥双重作用。通过添加二乙烯基锌进行乙烯基化。当产生一个新的立体中心时，一般会观察到中等至极好的立体控制。氨基可以通过在烷基化之前将中间体醛捕获为亚胺来引入。铟金属也可以促进还原消除-烯丙基化序列。所有的...
• Synthesis of Two New Quercitol (Deoxyinositol) Stereoisomers. Nuclear Magnetic Resonance and Optical Rotatory Configurational Proofs^1,2
  作者：G. E. McCasland、Stanley Furuta、L. F. Johnson、J. N. Shoolery

  DOI：10.1021/ja01471a026

  日期：1961.5
• Total Synthesis of Quercitols: (+)-allo-, (–)-proto-, (+)-talo-, (–)-gala-, (+)-gala-, neo-, and (–)-epi-Quercitol
  作者：Reinhard Brückner、Johannes Aucktor

  DOI：10.1055/s-0034-1379603

  日期：——

  The cyclohexenenones exo-and endo-2 were converted into the cyclohexenyl acetates exo-and endo-3 and exo-and endo-5 with a diastereoselectivity of >99: 1 (2 steps). Ether cleavage with DDQ in CH2Cl2/H2O (20: 1) and in situ ketal hydrolysis afforded the cyclohexenones 6 and 7 in up to 83% and 87% yield, respectively. Compound 6 was converted into (+)-allo- and (-)-proto-quercitol with a diastereoselectivity of 100: 0 (4 steps). Moreover, 6 was carried on to (-)-talo-quercitol whereas 7 furnished the four remaining title quercitols (3-5 steps) including both enantiomers of gala-quercitol.
• Desymmetrization of Cyclohexadienylsilanes. Regio-, Diastereo-, and Enantioselective Access to Sugar Mimics
  作者：Rémy Angelaud、Odile Babot、Trevor Charvat、Yannick Landais

  DOI：10.1021/jo991225z

  日期：1999.12.1

  Desymmetrization of cyclohexadienylsilanes available from Birch reduction of the corresponding arylsilanes is efficiently carried out using Sharpless asymmetric dihydroxylation and aminohydroxylation. Complete diastereocontrol and reasonable enantiocontrol have been attained during the preparation of the desired diols. An excellent regiocontrol has also been observed during aminohydroxylation of dienylsilanol 6b. The resulting diol 8 and hydroxycarbamate 27 have then been elaborated further, offering a straightforward access to various types of cyclitols, aminocyclitols, carbasugars, as well as the antibiotic palitantine 4. The complete functionalization of the original arylsilanes 5 is thus typically achieved in fewer than eight steps with high stereoselectivities and excellent overall yield.