5-thio-D-ribopyranose | 1910-72-1

• 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-D-ribopyranose
• 英文别名: 5-thio-D-ribose；D-Ribothiapyranose；(3R,4R,5S)-thiane-2,3,4,5-tetrol
• CAS: 1910-72-1；15354-46-8；15354-47-9；70267-99-1；86087-77-6；96896-26-3；96896-30-9
• 化学式: C₅H₁₀O₄S
• 分子量: 166.198
• InChiKey: QWVJFKXOINHVGD-SOOFDHNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  10
• 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：

  5-thio-D-ribopyranose 、 diethyl((benzylsulfonyl)methyl)phosphonate 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  A protecting group-free approach to C-glycosides using the Ramberg–Bäcklund reaction

  摘要：

  The one-pot conversion of unprotected monosaccharides directly into benzyisulfonylmethylene C-glycosides via a Horner-Wadsworth-Emmons/ring closure process is reported. Similar reactions giving sulfone-linked disaccharides are also discussed. One-pot transformations of unprotected monosaccharides to give styrenyl C-glycosides, by a tandem Horner Wadsworth-Emmons/ring closure-halogenation/Ramberg-Backlund sequence, is then described. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.10.099
• 作为产物：
  描述：

  1-O-acetyl-5-S-acetyl-2,3-O-isopropylidene-α-D-ribofuranose 在 Zerolit-225-H+ 、 水 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 5-thio-D-ribopyranose
  参考文献：
  名称：

  2，3-O-异亚丙基-5-硫代-d-核糖和5-硫代-d-核糖的方便合成；1,4-脱水-2,3-O-异亚丙基-α-d-核吡喃糖的合成

  摘要：

  摘要2，3-O-异亚丙基-d-呋喃核糖的顺序甲基化—乙酰化得到1-O-乙酰基-2,3-O-异亚丙基-5-O-甲磺酰基-β-d-核呋喃糖，将其转化为1-O -乙酰基-5-（S）-乙酰基-2,3-O-异亚丙基-5-硫代-β-d-核糖，其脱乙酰基得到2,3-O-异亚丙基-5-硫代-d-核糖。 β-吡喃糖形式，被水解为5-硫代-d-核糖。通过1-O-乙酰基-2,3-O-异亚丙基-5-O-甲磺酰基-β-d-的甲醇钠处理获得1,4-脱水-2,3-O-异亚丙基-α-d-核糖吡喃糖。通过1-（S）-乙酰基-2,3-O-异亚丙基-5-O-甲磺酰基类似地合成呋喃核糖和1,4-脱水-2,3-O-异亚丙基-5-硫代-α-d-核糖吡喃糖-5-硫代-α-d-呋喃核糖。

  DOI：

  10.1016/s0008-6215(99)00064-6

文献信息

• Synthesis of 4-cyanophenyl and 4-nitrophenyl 1,5-dithio-d-ribopyranosides as well as their 2-deoxy and 2,3-dideoxy derivatives possessing antithrombotic activity
  作者：Éva Bozó、Sándor Boros、János Kuszmann

  DOI：10.1016/s0008-6215(99)00175-5

  日期：1999.9

  1,2,3,4-Tetra-O-acetyl-5-thio-D-ribopyranose as well as its 1-bromide were used as donors in the reaction with 4-cyano- and 4-nitrobenzenethiol to give the corresponding thiogrycosides in different anomeric ratios depending on the reaction conditions. Zemplen deacetylation afforded 4-cyanophenyl as well as 4-nitrophenyl 1,5-dithio-alpha- and beta-D-ribopyranosides, respectively. 1,3,4-Tri-O-acetyl-2-deoxy-5-thio-D-erythro-pentopyranose was synthesized from methyl 2-deoxy-D-erythro-pentofuranoside and was coupled with 4-cyano- and 4-nitrobenzenethiol to give anomeric mixtures from which 4-cyanophenyl as well. as 4-nitrophenyl. 1,5-dithio-beta-D-erythro-pentopyranosides were isolated after deacetylation. 1,4-Di-O-acetyl-2,3-dideoxy-5-thio-D-glycero-pentopyranose was obtained starting from 1,2;5,6-di-O-isopropylidene-D-mannitol and used as the donor in the glycosylation reaction with 4-cyano- and 4-nitrobenzenethiol. The resulting anomeric mixtures were separated to give, after deacetylation, 4-cyanophenyl as well as 4-nitrophenyl 2,3-dideoxy-1,5-dithio-beta-D-glycero-pentopyranosides. All of these thioglycosides showed significant antithrombotic activity on rats after oral administration. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Convenient synthesis of 2,3-O-isopropylidene-5-thio-d-ribose and 5-thio-d-ribose; synthesis of 1,4-anhydro-2,3-O-isopropylidene-α-d-ribopyranose and 1,4-anhydro-2,3-O-isopropylidene-5-thio-α-d-ribopyranose
  作者：Andrea Fleetwood、Neil A. Hughes

  DOI：10.1016/s0008-6215(99)00064-6

  日期：1999.4

  Abstract Sequential mesylation–acetylation of 2,3-O-isopropylidene- d -ribofuranose gave 1-O-acetyl-2,3-O-isopropylidene-5-O-methanesulfonyl-β- d -ribofuranose that was converted into 1-O-acetyl-5-(S)-acetyl-2,3-O-isopropylidene-5-thio-β- d -ribose, deacetylation of which gave 2,3-O-isopropylidene-5-thio- d -ribose as the β-pyranose form, which was hydrolysed to 5-thio- d -ribose. 1,4-Anhydro-2,3-O-isopropylidene-α-

  摘要2，3-O-异亚丙基-d-呋喃核糖的顺序甲基化—乙酰化得到1-O-乙酰基-2,3-O-异亚丙基-5-O-甲磺酰基-β-d-核呋喃糖，将其转化为1-O -乙酰基-5-（S）-乙酰基-2,3-O-异亚丙基-5-硫代-β-d-核糖，其脱乙酰基得到2,3-O-异亚丙基-5-硫代-d-核糖。 β-吡喃糖形式，被水解为5-硫代-d-核糖。通过1-O-乙酰基-2,3-O-异亚丙基-5-O-甲磺酰基-β-d-的甲醇钠处理获得1,4-脱水-2,3-O-异亚丙基-α-d-核糖吡喃糖。通过1-（S）-乙酰基-2,3-O-异亚丙基-5-O-甲磺酰基类似地合成呋喃核糖和1,4-脱水-2,3-O-异亚丙基-5-硫代-α-d-核糖吡喃糖-5-硫代-α-d-呋喃核糖。
• A protecting group-free approach to C-glycosides using the Ramberg–Bäcklund reaction
  作者：Stéphane Jeanmart、Richard J.K. Taylor

  DOI：10.1016/j.tetlet.2005.10.099

  日期：2005.12

  The one-pot conversion of unprotected monosaccharides directly into benzyisulfonylmethylene C-glycosides via a Horner-Wadsworth-Emmons/ring closure process is reported. Similar reactions giving sulfone-linked disaccharides are also discussed. One-pot transformations of unprotected monosaccharides to give styrenyl C-glycosides, by a tandem Horner Wadsworth-Emmons/ring closure-halogenation/Ramberg-Backlund sequence, is then described. (c) 2005 Elsevier Ltd. All rights reserved.