(1R,2S,4S,5S)-cyclohexane-1,2,3,4,5-pentol | 131435-06-8

• 物质功能分类: 有机原料 - 醇、酚、酚醇类化合物及衍生物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2S,4S,5S)-cyclohexane-1,2,3,4,5-pentol
• 英文别名: 1D-1,2,3,5/4-cyclohexanepentol；(-)-2-deoxy-epi-inositol；2-deoxy-D-epi-inositol；D-6-Deoxy-myo-inositol；2-deoxy-epi-inositol；(+)-epi-quercitol；1D-6-deoxy-myo-inositol
• CAS: 131435-06-8
• 化学式: C₆H₁₂O₅
• 分子量: 164.158
• InChiKey: IMPKVMRTXBRHRB-GNFDWLABSA-N

物化性质

• 熔点：
  192.0 to 197.0 °C

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：

  (1R,2S,4S,5S)-cyclohexane-1,2,3,4,5-pentol 在 乙酸酐 、 对甲苯磺酸 、 二甲基亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 (2R,3R,4S,6R)-2,3:4,5-bis(isopropylidenedioxy)-1-cyclohexanone
  参考文献：
  名称：

  SYNTHESIS OF 1- AND 3-C-(AMINOMETHYL)-1,2,3,4,5-CYCLOHEXANEPENTOLS FROM (+)-epi-QUERCITOL1

  摘要：

  Oxidation of three di-O-isopropylidene derivatives 2a-4a, newly derived from (+)-epi-quercitol (1), with acetic anhydride in DMSO gave the corresponding ketones 5-7, which underwent aldol-type condensation with nitromethane under basic conditions to give selectively the protected derivatives 8a-10a of C-nitromethyl-1,2,3,4,5-cyclohexanepentols, respectively. On treatment with diazomethane in DMSO, the ketones 6 and 7 gave single spiro epoxides 11 and 12, the structures of which were confirmed by converting them into new C-(azidomethyl)cyclohexanepentols 16 and 17. The nitro compounds were hydrogenated in the presence of Raney nickel to give the amines isolated as the N-acetyl derivatives. Deprotection gave three new 1- and 3-C-aminomethyldeoxyinositols 15c-17c. The aminocyclitols obtained and their N-acetyl derivatives were assayed for inhibitory activity against examples of glycosidases.

  DOI：

  10.1081/car-100108284
• 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 、 18-冠醚-6 、 硫酸 、 氢气 、 sodium methylate 、 苄基三甲基氯化铵 、 sodium hydride 、 甲基磺酰氯 、 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 ℃ 、34.48 kPa 条件下， 反应 61.17h， 生成 (1R,2S,4S,5S)-cyclohexane-1,2,3,4,5-pentol
  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

• Synthesis of the Enantiomers of 6-Deoxy-myo-Inositol 1,3,4,5-Tetrakisphosphate, Structural Analogues ofmyo-Inositol 1,3,4,5-Tetrakisphosphate
  作者：Graeme Horne、Barry V. L. Potter

  DOI：10.1002/1521-3765(20010105)7:1<80::aid-chem80>3.0.co;2-b

  日期：2001.1.5

  for the synthesis of racemic 6-deoxy-myo-inositol 1,3,4,5-tetrakisphosphate [6-deoxy-DL-Ins(1,3,4,5)P4] and the chiral antipodes D- and L-6-deoxy-myo-inositol 1,3,4,5-tetrakisphosphate are described here. The racemic tetrakisphosphate was synthesised from DL-1,2-O-isopropylidene-myo-inositol in eight steps. Deoxygenation at C-6 was achieved following the Barton-McCombie procedure. Both chiral tetrakisphosphates

  D-肌醇 1,3,4,5-四磷酸 [Ins(1,3,4,5)P4] 从已建立的第二信使 D-肌醇 1,4,5-三磷酸 [Ins( 1,4,5)P4] 在受刺激的细胞中。尽管进行了广泛的研究，特别是关于其在介导细胞 Ca2+ 流入方面的潜在作用，但尚未描述这种磷酸肌醇的确切细胞功能。然而，已经在许多组织中鉴定出结合位点，并且它已显示出与 Ins(1,4,5)P3 协同作用。为了帮助阐明识别和激活受体所必需的 Ins(1,3,4,5)P4 部分的作用机制和结构要求，需要这种四磷酸的结构类似物。外消旋 6-deoxy-myo-inositol 1,3,4,5-tetrakisphosphate [6-deoxy-DL-Ins(1,3,4, 5)P4] 和手性对映体 D-和 L-6-脱氧-肌醇 1,3,4,5-四磷酸在这里进行了描述。外消旋四磷酸是由 DL-1,2-O-异亚丙基-肌醇分八步合成的。按照
• An Advantageous Synthesis of 1D- and 1L-1,2,3,5/4-Cyclohexanepentol
  作者：Marco A. Biamonte、Andrea Vasella

  DOI：10.1002/hlca.19980810319

  日期：——

  The title compounds D-10 and L-10 were prepared from 1 in eight steps and in a combined overall yield of 41–49%.

  标题化合物D- 10和L- 10由1步制备，共分八步，总收率达到41-49％。
• (+)-proto-Quercitol, a natural versatile chiral building block for the synthesis of the α-glucosidase inhibitors, 5-amino-1,2,3,4-cyclohexanetetrols
  作者：Sumrit Wacharasindhu、Wisuttaya Worawalai、Wimolpun Rungprom、Preecha Phuwapraisirisan

  DOI：10.1016/j.tetlet.2009.02.153

  日期：2009.5

  diastereomerically pure 5-amino-1,2,3,4-cyclohexanetetrols (6 and 11) and quercitol derivatives from naturally available (+)-proto-quercitol (1) is described. The stereochemistry of 1 is perfectly set up for regioselective protection of the hydroxy group which was further functionalized into the target aminocyclitol in a straightforward manner. The present approach provides a protocol for preparing aminocyclitols

  描述了由天然可得的（+）-原-槲皮醇（1）有效合成非对映体纯的5-氨基-1,2,3,4-环己烷四醇（6和11）和槲皮醇衍生物。立体化学1的建立是为了对羟基进行区域选择性保护，该羟基以直接的方式进一步官能化成目标氨基环糖醇。本方法提供了用于大量制备氨基环醇的方案。另外，使用改进的Mosher方法解决了（+）-原-槲皮醇的绝对立体化学。在合成的氨基环糖醇中，有11种可能通过IC抑制α-葡萄糖苷酶50值12.5μM，其比标准降糖药，阿卡波糖的大45倍的®。
• Convenient synthesis of 3- and 6-deoxy-d-myo-inositol phosphate analogues from (+)-epi- and (−)-vibo-quercitols
  作者：Seiichiro Ogawa、Yoji Tezuka

  DOI：10.1016/j.bmcl.2006.06.096

  日期：2006.10

  Starting from (+)-epi- and (-)-vibo-quercitols readily produced by bioconversion of myo-inositol, some biologically interesting phosphate and polyphosphate analogues, including the Ins(1,4,5)P(3) derivatives of 3-deoxy- and 6-deoxy-D-myo-inositol, could be readily prepared in a conventional manner. In addition, chemical modification at C-2 of the 3-deoxy Ins(1,4,5)P(3) provided 2-epimer, and 2-deoxy

  从通过肌醇生物转化而容易产生的（+）-表-和（-）-维-槲皮醇开始，一些生物学上有趣的磷酸盐和多磷酸盐类似物，包括3的Ins（1,4,5）P（3）衍生物-脱氧-和6-脱氧-D-肌醇可以容易地以常规方式制备。此外，3-脱氧Ins（1,4,5）P（3）在C-2处的化学修饰提供了2-电子异构体，2-脱氧和2-脱氧-2-氟形式。测定了获得的八种多磷酸盐类似物对PDH-Pase和PDH-K以及G6Pase的生物学活性，但没有一个被证明是阳性的。
• Highly stereoselective and stereospecific syntheses of a variety of quercitols from d-(−)-quinic acid
  作者：Tzenge-Lien Shih、Ya-Ling Lin、Wei-Shen Kuo

  DOI：10.1016/j.tet.2004.11.084

  日期：2005.2

  The highly stereoselective synthesis of (−)-epi-, (−)-allo- and neo-quercitols as well as stereospecific synthesis of (−)-talo- and (+)-gala-quercitols have been achieved. The general strategy is employing dihydroxylation of the isolated double bond of various kinds of protected chiral (1,4,5)-cyclohex-2-ene-triols, which are derived from d-(−)-quinic acid. The choosing of protecting groups from either

  （ - ） -的高度立体选择性合成外延- ， - （ - ） -异基因-和新-quercitols以及的立体定向合成（ - ） -距骨-和（+） -节日-quercitols已经实现。通用策略是对衍生自d-（-）-奎尼酸的各种受保护的手性（1,4,5）-环己-2-烯-三醇的分离的双键进行二羟基化。从BBA（2,3-丁烷丁二醛）或乙酰基中选择保护基将导致二羟基化的立体选择性的不同程度。另一方面，亚环己基缩醛部分归因于二羟基化过程中的立体特异性，以提供所需的分子。