(1R,2S,3R,4R)-4-(hydroxymethyl)cyclopentane-1,2,3-triol | 118013-56-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2S,3R,4R)-4-(hydroxymethyl)cyclopentane-1,2,3-triol
• 英文别名: (1R,2S,3R,4R)-4-(hydroxymethyl)cyclopentae-1,2,3-triol；(1R,2S,3R,4R)-4-hydroxymethylcyclopentane-1,2,3-triol；(1R,2S,3S,4R)-2,3,4-trihydroxycyclopentane-1-methanol；4a-carba-β-D-ribofuranose；β-D-carbaribofuranose；carba-β-D-ribofuranose
• CAS: 118013-56-2
• 化学式: C₆H₁₂O₄
• 分子量: 148.159
• InChiKey: PHKHGSSZAJVEQK-KAZBKCHUSA-N

物化性质

• 沸点：
  292.7±40.0 °C(Predicted)
• 密度：
  1.508±0.06 g/cm3(Predicted)

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：

  (1R,2S,3R,4R)-4-(hydroxymethyl)cyclopentane-1,2,3-triol 在 吡啶 、 camphor-10-sulfonic acid 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 (1R,2R,3S,4R)-4-acetoxy-1-(acetoxymethyl)-2,3-(isopropylidenedioxy)cyclopentane
  参考文献：
  名称：

  Syntheses of (1S,2S,3S,4R)- and (1R,2R,3S,4R)-2,3,4-trihydroxycyclopentane-1-methanol, carbocyclic analogs of .alpha.-L-arabinofuranose and .beta.-D-ribofuranose

  摘要：

  DOI：

  10.1021/jo00263a005
• 作为产物：
  描述：

  (+/-)-4β-Hydroxymethyl-2α,3α-(isopropylidenedioxy)cyclopentane-1β-ol 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到(1R,2S,3R,4R)-4-(hydroxymethyl)cyclopentane-1,2,3-triol
  参考文献：
  名称：

  Synthesis of α- and β-D-carbaribofuranose from (+)-norborn-5-en-2-one

  摘要：

  DOI：

  10.1016/0040-4039(90)80170-q

文献信息

• A Convenient Approach for Access to Both Carbapentofuranoses and Carbahexopyranoses. Stereocontrolled Synthesis of Enantiopure Carba-<scp>d</scp>-ribofuranoses, Carba-<scp>d</scp>-arabinofuranoses and Carba-<scp>l</scp>-gulopyranose
  作者：Subrata Ghosh、Tanurima Bhaumik、Niladri Sarkar、Abhijit Nayek

  DOI：10.1021/jo061717t

  日期：2006.12.1

  key step involves ring-closing metathesis of dienols 6 derived from a (R)-(+)-glyceraldehyde derivative 4 to form the substituted cyclopentenol 9 and cyclohexenol 34a. Stereocontrolled addition of hydroxyl groups followed by conversion of the ketal unit to hydroxymethyl group in these intermediates led to carbapentoses and -hexoses. Stereoselectivity during introduction of hydroxyl groups arises through

  报道了一种对映体纯净形式的Carcarbugars的新方法。关键步骤涉及衍生自（R）-（+）-甘油醛衍生物4的二烯醇6的闭环易位，以形成取代的环戊烯醇9和环己烯醇34a。在这些中间体中立体控制地添加羟基，然后将缩酮单元转化为羟甲基，导致产生碳戊糖和-己糖。在引入羟基的过程中，立体选择性是由烯丙基取代基构成的位阻引起的。本方法的显着特征是d-和l的可访问性系列的羧甲基戊糖，分别由β- d-和β- 1-碳氢呋喃呋喃糖酶17和20的合成说明。卡巴-α- d -ribofuranose 25，生物合成中间对抗生素芒霉素，也被从相同的环戊烯醇合成9。环戊烯醇9a中的官能团操纵也使能够获得呋喃糖呋喃糖32。本合成策略可以延长carbahexopyranose的合成，由卡巴-β-的合成如图升-gulopyranose 40B。
• Variable Strategy toward Carbasugars and Relatives. 2.¹ Diversity-Based Synthesis of β-<scp>d</scp>-Xylo, β-<scp>d</scp>-Ribo, β-<scp>l</scp>-Arabino, and β-<scp>l</scp>-Lyxo 4a-Carbafuranoses and (4a-Carbafuranosyl)thiols
  作者：Gloria Rassu、Luciana Auzzas、Luigi Pinna、Vincenzo Zambrano、Lucia Battistini、Franca Zanardi、Lucia Marzocchi、Domenico Acquotti、Giovanni Casiraghi

  DOI：10.1021/jo010585v

  日期：2001.11.1

  The silyloxy diene-based construction of carbasugars, previously exploited for the synthesis of four carbocyclic furanose and pyranose analogues, has been investigated further. By introducing a novel silylative cycloaldolization protocol and by adjusting a couple of minor transformations, the efficiency of this synthetic sequence was greatly improved. Through a series of lactone/thiolactone aldehyde cyclization precursors, four carbafuranoses (4a-carba-beta -D-xylofuranose, 4a-carba-beta -D-ribofuranose, 4a-carba-beta -L-arabinofuranose, and 4a-carba-beta -L-lyxofuranose) and four (carbafuranosyl)thiols [(4a-carba-beta -D-xylofuranosyl)thiol, (4a-carba-beta -D-ribofuranosyl)thiol, (4a-carba-beta -L-arabinofuranosyl)thiol, and (4a-carba-beta -L-lyxofuranosyl)thiol] were assembled. From this study, it was shown that these constructions tolerate a variety of precursors, and in many instances, they are suitable for scaling-up.
• Stereoselective synthesis of a novel natural carbasugar and analogues from hydroxymethylated cycloalkenone scaffolds
  作者：Rohan Rej、Navendu Jana、Shantasree Kar、Samik Nanda

  DOI：10.1016/j.tetasy.2012.03.001

  日期：2012.3

  Novel carbasugars from Streptomyces lincolnensis have been synthesized from an enantiomerically pure 5-hydroxymethyl-cyclohex-2-enone scaffold via a stereoselective approach. Several structural analogues of those carbasugars have also been synthesized in a stereoselective manner from hydroxymethylated cycloalkenone derivatives. (C) 2012 Elsevier Ltd. All rights reserved.
• MARSCHNER, CHRISTOPH;PENN, GERHARD;GRIENGL, HERFRIED, TETRAHEDRON LETT., 31,(1990) N0, C. 2873-2874
  作者：MARSCHNER, CHRISTOPH、PENN, GERHARD、GRIENGL, HERFRIED

  DOI：——

  日期：——
• TADANO, KIN-ICHI;HAKUBA, KEN;KIMURA, HIROSHI;OGAWA, SEIICHIRO, J. ORG. CHEM., 54,(1989) N, C. 276-279
  作者：TADANO, KIN-ICHI、HAKUBA, KEN、KIMURA, HIROSHI、OGAWA, SEIICHIRO

  DOI：——

  日期：——