(1R,2R,3S,4R)-4-(hydroxymethyl)cyclopentane-1,2,3-triol | 165875-03-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2R,3S,4R)-4-(hydroxymethyl)cyclopentane-1,2,3-triol
• 英文别名: 4a-carba-β-D-lyxofuranose
• CAS: 165875-03-6
• 化学式: C₆H₁₂O₄
• 分子量: 148.159
• InChiKey: PHKHGSSZAJVEQK-ARQDHWQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (1R,2R,3S,4R)-4-(hydroxymethyl)cyclopentane-1,2,3-triol 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以92%的产率得到1,2,3,5-Tetra-O-acetylcarba-β-D-lyxofuranose
  参考文献：
  名称：

  利用CrCl 2介导的多米诺骨牌反应和闭环易位的环戊醇的新方法。4a-carba-β-d-呋喃糖的合成

  摘要：

  使用Nozaki–Hiyama–Kishi条件和闭环复分解描述了一种由d-核糖合成环戊醇的有效方法。在该转化中，ω-脱氧-ω-碘呋喃核糖苷在CrCl 2的存在下进行还原消除，得到相应的烯烃-醛，该烯烃-醛在相同条件下被亲核试剂捕集，得到所需的二烯烃种类。用第二代Grubbs催化剂在二烯烃上进行的闭环易位反应产生了所需的碳环。

  DOI：

  10.1016/j.tetasy.2011.04.012
• 作为产物：
  描述：

  (3R,4R,5R)-5-((4S,5S)-5-Bromomethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-3,4-dihydroxy-dihydro-furan-2-one 在 吡啶 、 盐酸 、 sodium tetrahydroborate 、 sodium periodate 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 38.0h， 生成 (1R,2R,3S,4R)-4-(hydroxymethyl)cyclopentane-1,2,3-triol
  参考文献：
  名称：

  Highly Functionalized Cyclopentanes by Radical Cyclization of Unsaturated Bromolactones. 2. A Facile Synthesis of the First Carbaaldohexofuranoses and Their Conversion to Carbapentofuranoses

  摘要：

  A novel type of carbasugars, carbaaldohexofuranoses, has been prepared using a 5-exo-trig radical cyclization of C-2 substituted 2,3-unsaturated 7-bromoheptono-1,4-lactones as the key step. During the cyclization step, two-stereogenic centers were farmed with high stereoselectivity. The lactone moieties of the cyclopentane derivatives were reduced to the alcohols, and the following carbahexofuranoses were synthesized: carba-beta-D-mannofuranose, carba-alpha-L-glucofuranose and 5-amino-5-deoxycarba-alpha-L-glucofuranose. Side chain degradation of the two former compounds gave the carbapentofuranoses: carba-alpha-L-xylofuranose and carba-beta-D-lyxofuranose.

  DOI：

  10.1021/jo971928l

文献信息

• Synthesis of 4a-Carba-<scp>d</scp>-lyxofuranose Derivatives and Their Evaluation as Inhibitors of GH38 α-Mannosidases
  作者：Mária Zajičková、Ján Moncoľ、Sergej Šesták、Juraj Kóňa、Miroslav Koóš、Maroš Bella

  DOI：10.1002/ejoc.201801586

  日期：2019.2.7

  4a‐Carba‐β‐d‐lyxofuranose and its three derivatives were synthesized and evaluated as inhibitors of GH38 α‐mannosidases. Only 1‐amino‐4a‐carba‐β‐d‐lyxofuranose exhibited reasonable inhibitory activity (IC50 = 200 µm) against Golgi α‐mannosidase from Drosophila melanogaster (GMIIb). The inhibitory activity of 1‐amino‐4a‐carba‐β‐d‐lyxofuranose against GMIIb was discussed by means of molecular modelling

  合成了4a-Carba-β- d-木糖呋喃糖及其三种衍生物，并将其评估为GH38α-甘露糖苷酶的抑制剂。只有1氨基-4a卡巴-β- d -lyxofuranose展出合理的抑制活性（IC 50 = 200μ米）对来自高尔基体α甘露糖苷酶黑腹果蝇（GMIIb）。通过分子模拟讨论了1-氨基-4a-卡巴-β - d-呋喃糖对GMIIb的抑制活性。
• Synthesis of All Stereoisomeric Carbapentofuranoses
  作者：Christoph Marschner、Judith Baumgartner、Herfried Griengl

  DOI：10.1021/jo00121a046

  日期：1995.8

  All carbocyclic analogs of the pentofuranoses were synthesized starting from norborn-5-en-2-one (1). By using either base- or acid-catalyzed Baeyer-Villiger reaction of 1, the central intermediates 2 and 3 were obtained. The required functionalization of the olefinic double bond was achieved either by cis-hydroxylation in the case of the ribo, lyre, and alpha-xylo derivatives or by epoxidation and subsequent opening with aqueous perchloric acid. In the latter case, a pronounced selectivity for opening the epoxy alcohol in the 3-position was found. If an epoxy acetate with both functions on the same side of the ring was used, the epoxide was opened in the 2-position by neighboring group participation of the acetate. The requisite side chain degradation was accomplished either by conversion of the ester into an olefin and subsequent dihydroxylation/cleavage reaction or by Curtius rearrangement to the amine and its conversion into an acetate.