1-deoxy-5-thio-D-mannopyrano-3,6-lactone | 1245608-81-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻烷
• 英文名称: 1-deoxy-5-thio-D-mannopyrano-3,6-lactone
• 英文别名: (1S,4S,5R,8S)-4,8-dihydroxy-6-oxa-2-thiabicyclo[3.2.1]octan-7-one
• CAS: 1245608-81-4
• 化学式: C₆H₈O₄S
• 分子量: 176.193
• InChiKey: WNJSHNDCJNHSLC-LECHCGJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  92.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-deoxy-5-thio-D-mannopyrano-3,6-lactone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以74%的产率得到1-deoxythiomannojirimycin
  参考文献：
  名称：

  Enantioselective and Protecting Group-Free Synthesis of 1-Deoxythionojirimycin, 1-Deoxythiomannojirimycin, and 1-Deoxythiotalonojirimycin

  摘要：

  1-Deoxythioglyconojirimycins were synthesized by using a protecting group-free strategy, starting from readily available carbohydrates, in good overall yield. Use of benzyl-triethylammonium tetrathiomolybdate, [BnEt3N](2)MoS4, as a sulfur transfer reagent and borohydride exchange resin (BER) reduction of a lactone enabled the efficient synthesis of the title compounds.

  DOI：

  10.1021/jo1010125
• 作为产物：
  描述：

  2,6-Dibromo-2,6-dideoxy-D-glucono-1,4-lactone 在 benzyltriethylammonium tetrathiomolybdate 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 以59%的产率得到1-deoxy-5-thio-D-mannopyrano-3,6-lactone
  参考文献：
  名称：

  Enantioselective and Protecting Group-Free Synthesis of 1-Deoxythionojirimycin, 1-Deoxythiomannojirimycin, and 1-Deoxythiotalonojirimycin

  摘要：

  1-Deoxythioglyconojirimycins were synthesized by using a protecting group-free strategy, starting from readily available carbohydrates, in good overall yield. Use of benzyl-triethylammonium tetrathiomolybdate, [BnEt3N](2)MoS4, as a sulfur transfer reagent and borohydride exchange resin (BER) reduction of a lactone enabled the efficient synthesis of the title compounds.

  DOI：

  10.1021/jo1010125

文献信息

• Enantioselective and Protecting Group-Free Synthesis of 1-Deoxythionojirimycin, 1-Deoxythiomannojirimycin, and 1-Deoxythiotalonojirimycin
  作者：Thanikachalam Gunasundari、Srinivasan Chandrasekaran

  DOI：10.1021/jo1010125

  日期：2010.10.1

  1-Deoxythioglyconojirimycins were synthesized by using a protecting group-free strategy, starting from readily available carbohydrates, in good overall yield. Use of benzyl-triethylammonium tetrathiomolybdate, [BnEt3N](2)MoS4, as a sulfur transfer reagent and borohydride exchange resin (BER) reduction of a lactone enabled the efficient synthesis of the title compounds.