2,3-O-isopropylidene-α-L-lyxofuranose | 76249-51-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-O-isopropylidene-α-L-lyxofuranose
• 英文别名: 2,3-O-Isopropylidene-α-L-lyxose；(3aR,4R,6S,6aR)-6-(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-ol
• CAS: 76249-51-9
• 化学式: C₈H₁₄O₅
• 分子量: 190.196
• InChiKey: OYYTWUSIDMJZCP-BDVNFPICSA-N

物化性质

• 沸点：
  337.4±42.0 °C(Predicted)
• 密度：
  1.267±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,5-二异氰酸硝基苯 、 2,3-O-isopropylidene-α-L-lyxofuranose 以4.8 mg的产率得到1,5-di-O-(3,5-dinitrophenyl)carbamoyl-2,3-O-isopropylidene-α-L-lyxofuranose
  参考文献：
  名称：

  Tsukamoto, Sachiko; Kaneko, Koh; Hayashi, Koji, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 3, p. 637 - 641

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-Isopropylidene-D-gulono-γ-lactone 在 sodium tetrahydroborate 、 sodium periodate 作用下， 生成 2,3-O-isopropylidene-α-L-lyxofuranose
  参考文献：
  名称：

  First synthesis of aldopentono-1,4-thiolactones

  摘要：

  A convenient synthesis of enantiomerically pure aldopentono-1,4-thiolactones is described. Thus, 4-thio-D-ribono-1,4-lactone (12) has been prepared from D-gluono-1,4-lactone (1), via its 2,3-O-isopropylidene derivative 3. The 5,6-glycol system of 3 was oxidized with NaIO4. Chemoselective reduction of the resulting aldehyde function with NaBH3CN led to 2,3-O-isopropylidene-L-lyxono-1,4-lactone (7). Tosylation of 7 and subsequent treatment of the tosylate 8 with sodium methoxide afforded methyl 4,5-epoxy-2,3-O-isopropylidene-L-lyxonate (9) as a key intermediate. Treatment of 9 with thiourea gave the 4,5-thiirane derivative having the D-ribo configuration (10). Regioselective opening of the thiirane ring and simultaneous thiolactonization took place by heating 10 with KOAc-HOAc-DMF. The resulting 5-O-acetyl-2,3-0-isopropylidene-4-thio-D-ribono-1,4-lactone (11) was readily converted, by acid removal (2 % HCI) of the protecting groups, into the crystalline thiolactone 12. A similar approach was employed for the synthesis of 4-thio-L-lyxono-1,4-lactone (19), starting from D-ribono-1,4-lactone (13).

  DOI：

  10.1021/jo00079a034

文献信息

• Efficient “Dehomologation” of Di-<i>O-</i>isopropylidenehexofuranose Derivatives To Give <i>O-</i>Isopropylidenepentofuranoses by Sequential Treatment with Periodic Acid in Ethyl Acetate and Sodium Borohydride
  作者：Meiqiang Xie、David A. Berges、Morris J. Robins

  DOI：10.1021/jo960355u

  日期：1996.1.1
• TSUKAMOTO, SACHIKO;KANEKO, KOH;HAYASHI, KOJI, CHEM. AND PHARM. BULL., 37,(1989) N, C. 637-641
  作者：TSUKAMOTO, SACHIKO、KANEKO, KOH、HAYASHI, KOJI

  DOI：——

  日期：——
• First synthesis of aldopentono-1,4-thiolactones
  作者：Oscar Varela、Patricia A. Zunszain

  DOI：10.1021/jo00079a034

  日期：1993.12

  A convenient synthesis of enantiomerically pure aldopentono-1,4-thiolactones is described. Thus, 4-thio-D-ribono-1,4-lactone (12) has been prepared from D-gluono-1,4-lactone (1), via its 2,3-O-isopropylidene derivative 3. The 5,6-glycol system of 3 was oxidized with NaIO4. Chemoselective reduction of the resulting aldehyde function with NaBH3CN led to 2,3-O-isopropylidene-L-lyxono-1,4-lactone (7). Tosylation of 7 and subsequent treatment of the tosylate 8 with sodium methoxide afforded methyl 4,5-epoxy-2,3-O-isopropylidene-L-lyxonate (9) as a key intermediate. Treatment of 9 with thiourea gave the 4,5-thiirane derivative having the D-ribo configuration (10). Regioselective opening of the thiirane ring and simultaneous thiolactonization took place by heating 10 with KOAc-HOAc-DMF. The resulting 5-O-acetyl-2,3-0-isopropylidene-4-thio-D-ribono-1,4-lactone (11) was readily converted, by acid removal (2 % HCI) of the protecting groups, into the crystalline thiolactone 12. A similar approach was employed for the synthesis of 4-thio-L-lyxono-1,4-lactone (19), starting from D-ribono-1,4-lactone (13).
• Tsukamoto, Sachiko; Kaneko, Koh; Hayashi, Koji, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 3, p. 637 - 641
  作者：Tsukamoto, Sachiko、Kaneko, Koh、Hayashi, Koji

  DOI：——

  日期：——