(-)-2-deoxy-allo-inositol | 40617-62-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-2-deoxy-allo-inositol
• 英文别名: (-)-gala quercitol；(-)-gala-quercitol；(1S)-cyclohexane-1r,2c,3t,4t,5c-pentaol；(1S)-Cyclohexan-1r,2c,3t,4t,5c-pentaol；(1S)-Cyclohexanpentol-(1r.2c.3t.4t.5c)；(-)(1R)-2-Desoxy-allo-inosit
• CAS: 40617-62-7
• 化学式: C₆H₁₂O₅
• 分子量: 164.158
• InChiKey: IMPKVMRTXBRHRB-BYIBVSMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.81
• 重原子数：
  11.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  101.15
• 氢给体数：
  5.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (-)-2-deoxy-allo-inositol 、 乙酸酐 在 sodium acetate 作用下， 生成 (-)-penta-O-acetyl-2-deoxy-allo-inositol
  参考文献：
  名称：

  Synthesis of Two New Quercitol (Deoxyinositol) Stereoisomers. Nuclear Magnetic Resonance and Optical Rotatory Configurational Proofs^1,2

  摘要：

  DOI：

  10.1021/ja01471a026
• 作为产物：
  描述：

  甲基-Β-D-吡喃半乳糖苷 在 palladium on activated charcoal 吡啶 、 四氯化碳 、 氢氧化钾 、 硫酸 、 氢气 、 苄基三甲基氯化铵 、 sodium hydride 、 lithium tri-t-butoxyaluminum hydride 、 硫脲 、 三苯基膦 、 mercury dichloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， -40.0~110.0 ℃ 、20.68 kPa 条件下， 反应 40.17h， 生成 (-)-2-deoxy-allo-inositol
  参考文献：
  名称：

  Stereoselective synthesis of 6-deoxy and 3,6-dideoxy-D-myo-inositol precursors of deoxy-myo-inositol phosphate analogues from D-galactose

  摘要：

  The synthesis of chiral protected D-6-deoxy-myo-inositol derivatives from D-galactose is described. Ferrier rearrangement of hexenogalactopyranosides has been employed to produce the corresponding 6-deoxy-cyclohexanone polyols. The stereoselectivity of the carbocyclic transformation was discussed on the basis of the experimental data and a mechanism has been proposed. From deoxy-inososes, the access to a variety of 6-deoxy and 3,6-dideoxy-myo-inositol was performed to prepare suitable monool, diol and triol precursors for the synthesis of D-deoxy-myo-inositol phosphate analogues. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)10101-6

文献信息

• 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...
• Stereoselective syntheses of (+)-proto, (−)-gala quercitols and carba-l-rhamnose from d-(−)-quinic acid
  作者：Andiappan Murugan、Anuj K. Yadav、Mukund K. Gurjar

  DOI：10.1016/j.tetlet.2005.07.052

  日期：2005.9

  Efficient syntheses of (+)-proto, (−)-gala quercitols and carba-l-rhamnose from d-(−)-quinic acid are described.

  （+）的有效合成-原，（ - ） -晚会quercitols和从d卡巴-L-鼠李糖- （ - ） -奎尼酸中描述。
• 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.
• Landais, Yannick, Chimia, 1998, vol. 52, # 3, p. 104 - 111
  作者：Landais, Yannick

  DOI：——

  日期：——
• Desymmetrization of a Silyl-2,5-cyclohexadiene. Synthesis of (+)-Conduritol E and (−)-2-Deoxy-<i>allo</i>-inositol
  作者：Rémy Angelaud、Yannick Landais

  DOI：10.1021/jo960814r

  日期：1996.1.1