5-thio-L-fucose | 131064-76-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻烷
• 英文名称: 5-thio-L-fucose
• 英文别名: 5-deoxy-5-thio-α-L-fucopyranose；I+/--L-Galactopyranose, 6-deoxy-5-thio-；(2R,3S,4R,5S,6S)-6-methylthiane-2,3,4,5-tetrol
• CAS: 131064-76-1
• 化学式: C₆H₁₂O₄S
• 分子量: 180.225
• InChiKey: QVIFEFBNURQVKR-SXUWKVJYSA-N

物化性质

• 熔点：
  159-160 °C(Solv: methanol (67-56-1))
• 沸点：
  321.8±42.0 °C(Predicted)
• 密度：
  1.582±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  106
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 5-thio-L-fucose 在 吡啶 作用下， 生成 1,2,3,4-tetra-O-acetyl-5-thio-α-L-fucopyranose
  参考文献：
  名称：

  从d-阿拉伯糖轻松合成5-thio-1-fucose和5-thio-d-阿拉伯糖

  摘要：

  摘要由5-O-三苯甲基-d-阿拉伯糖基呋喃糖或d-阿拉伯糖二乙基二硫缩醛在C-5上一键延伸，合成了11个步骤的5-巯基-呋喃葡萄糖四乙酸酯。实现了将醚中的MeLi高度非对映选择性地添加到1,2-O-异亚丙基-β-d-阿拉伯糖基戊二醛-1,4-呋喃糖衍生物中，得到相应的6-脱氧-β-d-呋喃糖异构体。良品率高。通过在HMPA中用KSAc取代5-甲苯磺酸酯并反转构型，将硫原子引入6-脱氧-d-呋喃呋喃糖衍生物的C-5处，得到5-硫-1-呋喃葡萄糖。还由6-脱氧-β-d-呋喃糖衍生物制备3-O-取代的-1-岩藻糖衍生物。5-硫代-1-呋喃糖的5-脱甲基类似物5-噻吩基-阿拉伯吡喃喃糖四乙酸酯也由5个步骤由5-O-三苯甲基-d-阿拉伯呋喃糖合成。

  DOI：

  10.1016/0008-6215(95)00323-1
• 作为产物：
  描述：

  在 lithium aluminium tetrahydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 3.0h， 生成 5-thio-L-fucose
  参考文献：
  名称：

  Applications of Cyclic Sulfates of vic-Diols:  Synthesis of Episulfides, Olefins, and Thio Sugars

  摘要：

  A new efficient and expeditious one-pot synthesis of thiiranes and olefins from cyclic sulfates of vic-diols is described. Opening of cyclic sulfates with potassium thioacetate or potassium thiocyanate followed by treatment with sodium methoxide led to episulfides. Olefins were obtained when potassium selenocyanate was used as nucleophile, and the obtained monoesters were treated with sodium borohydride. This method was applied to acyclic polyols derived from chiral glycerine, 1,2-isopropylidenehexofuranoses with different subtituents at C-3, and dimethyl acetals derived from pentoses and hexoses. The methodology is highly versatile, and its applicability has been demonstrated by the synthesis of different 4- and 5-thiosugars by opening of the thiirane ring with sodium acetate or lithium aluminum hydride. Reduction with lithium aluminum hydride of the thiocyanate sulfate potassium salt obtained by the opening of cyclic sulfate with KSCN allowed the direct synthesis of 5-deoxy-4-thio- and 6-deoxy-5-thiosugars. Cyclic thiosugars with the sulfur atom in the ring are obtained by acidic hydrolysis of the 5-thiol derivatives of 1,2-O-isopropylidenehexofuranoses and 4-thiopentose dimethyl acetals. Using this method, an efficient synthesis of 5-thio-L-fucose as well as the synthesis of 2,5-dideoxy-4-thiofuranose is described.

  DOI：

  10.1021/jo962066b

文献信息

• Syntheses of L-Fucopyranose and Its Homologs with Ring Heteroatoms Other than Oxygen. Stereocontrolled Conversion of a Common D-Arabinofuranoside Intermediate.
  作者：Shunya Takahashi、Hiroyoshi Kuzuhara

  DOI：10.1246/cl.1992.21

  日期：——

  l-Fucopyranose and a couple of l-fucosidase inhibitors, 5-deoxy-5-thio-l-fucopyranose and 1,5-dideoxy-1,5-imino-l-fucitol, were prepared from a common pentose intermediate with α-d-arabino configuration. Stereoselectivities on carbon chain elongation of the key intermediate were successfully controlled by choosing the appropriate organometallic reagents.

  l-岩藻吡喃糖以及几种l-岩藻苷酶抑制剂，5-脱氧-5-硫-l-岩藻吡喃糖和1,5-二脱氧-1,5-亚氨基-l-岩藻醇，均由具有α-d-阿拉伯糖构型的普通戊糖中间体制备而成。通过选择适当的金属有机试剂，成功控制了关键中间体碳链延伸的立体选择性。
• A Facile Synthesis of 5-Thio-L-fucose and 3-O-Allyl-L-fucose Triacetate from D-Arabinose.
  作者：Hironobu Hashimoto、Masayuki Izumi

  DOI：10.1246/cl.1992.25

  日期：——

  5-Thio-L-fucose and 3-O-allyl-L-fucose triacetate were synthesized from D-arabinose via D-arabino-pentodialdo-1,4-furanose derivative

  5-硫代-L-岩藻糖和3-O-烯丙基-L-岩藻糖三乙酸酯由D-阿拉伯糖通过D-阿拉伯-戊二醛-1,4-呋喃糖衍生物合成
• HASHIMOTO, HIRONOBU;FUJIMORI, TAKETOSHI;YUASA, HIDEYA, J. CARBOHYDR. CHEM. , 9,(1990) N, C. 683-694
  作者：HASHIMOTO, HIRONOBU、FUJIMORI, TAKETOSHI、YUASA, HIDEYA

  DOI：——

  日期：——
• Applications of Cyclic Sulfates of <i>vic</i>-Diols:  Synthesis of Episulfides, Olefins, and Thio Sugars
  作者：Francisco G. Calvo-Flores、Pilar García-Mendoza、Fernando Hernández-Mateo、Joaquín Isac-García、Francisco Santoyo-González

  DOI：10.1021/jo962066b

  日期：1997.6.13

  A new efficient and expeditious one-pot synthesis of thiiranes and olefins from cyclic sulfates of vic-diols is described. Opening of cyclic sulfates with potassium thioacetate or potassium thiocyanate followed by treatment with sodium methoxide led to episulfides. Olefins were obtained when potassium selenocyanate was used as nucleophile, and the obtained monoesters were treated with sodium borohydride. This method was applied to acyclic polyols derived from chiral glycerine, 1,2-isopropylidenehexofuranoses with different subtituents at C-3, and dimethyl acetals derived from pentoses and hexoses. The methodology is highly versatile, and its applicability has been demonstrated by the synthesis of different 4- and 5-thiosugars by opening of the thiirane ring with sodium acetate or lithium aluminum hydride. Reduction with lithium aluminum hydride of the thiocyanate sulfate potassium salt obtained by the opening of cyclic sulfate with KSCN allowed the direct synthesis of 5-deoxy-4-thio- and 6-deoxy-5-thiosugars. Cyclic thiosugars with the sulfur atom in the ring are obtained by acidic hydrolysis of the 5-thiol derivatives of 1,2-O-isopropylidenehexofuranoses and 4-thiopentose dimethyl acetals. Using this method, an efficient synthesis of 5-thio-L-fucose as well as the synthesis of 2,5-dideoxy-4-thiofuranose is described.
• A facile synthesis of 5-thio-l-fucose and 5-thio-d-arabinose from d-arabinose
  作者：Masayuki Izumi、Osamu Tsuruta、Hironobu Hashimoto

  DOI：10.1016/0008-6215(95)00323-1

  日期：1996.1

  A 3-O- substituted- l -fucose derivative was also prepared from 6-deoxy-β- d -altrofuranose derivatives. 5-Thio- d -arabinopyranose tetraacetate, the 5-demethyl analog of 5-thio- l -fucose, was also synthesized from 5-O- trityl- d -arabinofuranose in 5 steps. 5-Thio- d -arabinose showed weak inhibitory activity against α- l -fucosidase from bovine kidney ( K i = 0.77 mM ).

  摘要由5-O-三苯甲基-d-阿拉伯糖基呋喃糖或d-阿拉伯糖二乙基二硫缩醛在C-5上一键延伸，合成了11个步骤的5-巯基-呋喃葡萄糖四乙酸酯。实现了将醚中的MeLi高度非对映选择性地添加到1,2-O-异亚丙基-β-d-阿拉伯糖基戊二醛-1,4-呋喃糖衍生物中，得到相应的6-脱氧-β-d-呋喃糖异构体。良品率高。通过在HMPA中用KSAc取代5-甲苯磺酸酯并反转构型，将硫原子引入6-脱氧-d-呋喃呋喃糖衍生物的C-5处，得到5-硫-1-呋喃葡萄糖。还由6-脱氧-β-d-呋喃糖衍生物制备3-O-取代的-1-岩藻糖衍生物。5-硫代-1-呋喃糖的5-脱甲基类似物5-噻吩基-阿拉伯吡喃喃糖四乙酸酯也由5个步骤由5-O-三苯甲基-d-阿拉伯呋喃糖合成。