4a-carba-β-L-lyxofuranose | 113299-30-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4a-carba-β-L-lyxofuranose
• 英文别名: (1S,2S,3R,4S)-4-(hydroxymethyl)cyclopentane-1,2,3-triol
• CAS: 113299-30-2
• 化学式: C₆H₁₂O₄
• 分子量: 148.159
• InChiKey: PHKHGSSZAJVEQK-AZGQCCRYSA-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 、 4a-carba-β-L-lyxofuranose 在 吡啶 作用下， 生成 (1S,2R,3S,4S)-2,3,4-triacetoxy-1-(acetoxymethyl)cyclopentane
  参考文献：
  名称：

  Transformation of D-erythrose to some pseudoaldopentofuranoses. Syntheses of (1S,2R,3S,4S)-, (1R,2R,3S,4S)-, and (1R,2S,3S,4S)-2,3,4-trihydroxy-1-(hydroxymethyl)cyclopentanes and (1R,2S,3R,4R)-2,3-dihydroxy-4-(hydroxymethyl)-1-cyclopentanamine

  摘要：

  DOI：

  10.1021/jo00242a016
• 作为产物：
  描述：

  (5S)-5-[(1R,2R)-1-[tert-butyl(dimethyl)silyl]oxy-2,3-dihydroxypropyl]oxolan-2-one 在 盐酸 、 sodium periodate 、 锂硼氢 、 silica gel 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 13.5h， 生成 4a-carba-β-L-lyxofuranose
  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

• 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.
• TADANO, KIN-ICHI;HOSHINO, MASAHIDE;OGAWA, SEIICHIRO;SUAMI, TETSUO, J. ORG. CHEM., 53,(1988) N 7, 1427-1432
  作者：TADANO, KIN-ICHI、HOSHINO, MASAHIDE、OGAWA, SEIICHIRO、SUAMI, TETSUO

  DOI：——

  日期：——