(1S,2S,3S,4S)-4-(hydroxymethyl)cyclopentane-1,2,3-triol | 105265-95-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2S,3S,4S)-4-(hydroxymethyl)cyclopentane-1,2,3-triol
• 英文别名: (1~{S},2~{S},3~{S},4~{S})-4-(hydroxymethyl)cyclopentane-1,2,3-triol
• CAS: 105265-95-0
• 化学式: C₆H₁₂O₄
• 分子量: 148.159
• InChiKey: PHKHGSSZAJVEQK-BXKVDMCESA-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 、 (1S,2S,3S,4S)-4-(hydroxymethyl)cyclopentane-1,2,3-triol 在 吡啶 作用下， 生成 (1S,2S,3S,4S)-2,3,4-triacetoxy-1-(acetoxymethyl)cyclopentane
  参考文献：
  名称：

  A novel transformation of four aldoses to some optically pure pseudohexopyranoses and a pseudopentofuranose, carbocyclic analogs of hexopyranoses and pentofuranose. Synthesis of derivatives of (1S,2S,3R,4S,5S)-, (1S,2S,3R,4R,5S)-, (1R,2R,3R,4R,5S)-, (1S,2S,3R,4S,5R)-2,3,4,5-tetrahydroxy-1-(hydroxymethyl)cyclohexanes and (1S,2S,3S,4S)-2,3,4-trihydroxy-1(hydroxymethyl)cyclopentane

  摘要：

  DOI：

  10.1021/jo00386a011
• 作为产物：
  描述：

  (1'S,4''R,5R)-5-[(2,2-dimethyl-1,3-dioxolan-4-yl)hydroxymethyl]-5H-furan-2-one 在 2,6-二甲基吡啶 、 盐酸 、 sodium tetrahydroborate 、 sodium periodate 、 锂硼氢 、 silica gel 、 溶剂黄146 、 三乙胺 、 N,N-二异丙基乙胺 、 nickel dichloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 38.5h， 生成 (1S,2S,3S,4S)-4-(hydroxymethyl)cyclopentane-1,2,3-triol
  参考文献：
  名称：

  Variable Strategy toward Carbasugars and Relatives. 2.¹ Diversity-Based Synthesis of β-d-Xylo, β-d-Ribo, β-l-Arabino, and β-l-Lyxo 4a-Carbafuranoses and (4a-Carbafuranosyl)thiols

  摘要：

  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.

  DOI：

  10.1021/jo010585v

文献信息

• A NEW TRANSFORMATION OF ALDOSE DERIVED SYNTHONS TO PSEUDO-HEXOPYRANOSE OR PSEUDO-PENTOFURANOSE DERIVATIVES
  作者：Kin-ichi Tadano、Hiroo Maeda、Masahide Hoshino、Youichi Iimura、Tetsuo Suami

  DOI：10.1246/cl.1986.1081

  日期：1986.7.5

  The d-ribose or d-erythrose derived acyclic synthon, which possesses a 2-malonyl carbon chain at C-1 position, was cyclized stereoselectively to a six- or five-membered carbocycle. Those carbocycles were converted into pseudo-β-l-mannopyranose derivatives or pseudo-β-l-arabinofuranose derivatives efficeintly.

  源自于d-核糖或d-赤藓糖的无环合成物，在C-1位拥有一个2-马隆基碳链，经过立体选择性环化形成了六元或五元碳环。这些碳环有效地转化为伪-β-l-甘露糖吡喃糖衍生物或伪-β-l-阿拉伯糖呋喃糖衍生物。
• Synthesis of 4a-carba-β-l-lyxofuranose, 4a-carba-β-l-arabinofuranose and 2,2,5-trimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one using Mn/CrCl3 mediated domino reactions and ring closing metathesis
  作者：Girija Prasad Mishra、Bejugam Santhosh Kumar、B. Venkateswara Rao

  DOI：10.1016/j.tetasy.2012.07.014

  日期：2012.8

  A common method for the synthesis of 4a-carba-beta-L-lyxofuranose and 4a-carba-beta-L-arabinofuranose from D-mannose and 2,2,5-trimethy1-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one from o-ribose is described using catalytic Nozaki-Hiyama-Kishi (NHK) conditions and ring closing metathesis (RCM). In this transformation, omega-deoxy-omega-iodo manno/ribo furanoside undergoes reductive elimination in the presence of Mn/CrCl3 to give the corresponding olefin-aldehyde which was trapped by nucleophile under the same conditions to afford the desired diolefinic species. The ring closing metathesis reaction on these diolefinic species with Grubbs second generation catalyst produced the required carbocycles. (c) 2012 Elsevier Ltd. All rights reserved.
• 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.
• (R)-2,3-O-Cyclohexylideneglyceraldehyde: a useful template for a simple entry into carbafuranose stereoisomers
  作者：Sibanarayan Tripathy、Angshuman Chattopadhyay

  DOI：10.1016/j.tetasy.2012.09.007

  日期：2012.10

  (R)-2,3-O-Cyclohexylideneglyceraldehyde 1 provides a simple route for the preparation of carbafuranoses. This has been exemplified by the preparation of 10c and 10d, the derivatives of carba D-xylofuranose and carba-L-arabinofuranose respectively, starting from homoallylic alcohol 2a derived from 1. The key step in this protocol was the intramolecular allylation of 9 promoted by several metals under wet conditions that resulted in the construction of the carbafuranose skeleton of 10. The potential of several metals regarding the efficacy and stereoselectivity of this crucial intramolecular allylation reaction has been studied. The moderate stereoselectivity in all of the successful intramolecular allylations of 9 yielding both D-10c and L-10d as the major products contributed significantly in attaining stereo-divergence in this route. The utility of this route was due to the easy availability of 1, and the operational simplicity as well as scalability of all of the reactions involved. (C) 2012 Elsevier Ltd. All rights reserved.
• A novel transformation of four aldoses to some optically pure pseudohexopyranoses and a pseudopentofuranose, carbocyclic analogs of hexopyranoses and pentofuranose. Synthesis of derivatives of (1S,2S,3R,4S,5S)-, (1S,2S,3R,4R,5S)-, (1R,2R,3R,4R,5S)-, (1S,2S,3R,4S,5R)-2,3,4,5-tetrahydroxy-1-(hydroxymethyl)cyclohexanes and (1S,2S,3S,4S)-2,3,4-trihydroxy-1(hydroxymethyl)cyclopentane
  作者：Kinichi Tadano、Hiroo Maeda、Masahide Hoshino、Youichi Iimura、Tetsuo Suami

  DOI：10.1021/jo00386a011

  日期：1987.5