methyl 2-deoxy-3,5-di-O-p-toluenesulfonyl-D-erythro-pentofuranoside | 60110-69-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-deoxy-3,5-di-O-p-toluenesulfonyl-D-erythro-pentofuranoside
• 英文别名: methyl 2-deoxy-3,5-di-O-tosyl-D-ribofuranoside；methyl-[bis-O-(toluene-4-sulfonyl)-ξ-D-erythro-2-deoxy-pentofuranoside]；Methyl-[bis-O-(toluol-4-sulfonyl)-ξ-D-erythro-2-desoxy-pentofuranosid]；[(2R,3S)-5-methoxy-3-(4-methylphenyl)sulfonyloxyoxolan-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 60110-69-2；60110-72-7；65310-05-6
• 化学式: C₂₀H₂₄O₈S₂
• 分子量: 456.538
• InChiKey: ZXYDQQBNAJVTFQ-ABZYKWASSA-N

物化性质

• 沸点：
  615.0±55.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2-deoxy-3,5-di-O-p-toluenesulfonyl-D-erythro-pentofuranoside 在 copper(l) iodide 、 正丁基锂 、 溶剂黄146 作用下， 以 乙醚 为溶剂， 反应 15.5h， 生成 (13R,9Z,11E)-13-hydroxy-9,11-octadecadienoic acid
  参考文献：
  名称：

  A concise synthesis of (R)-hydroxy-E,Z-diene fatty acids: preparation of 12(R)-hete, tetranor-12(R)-hete, and 13(R)-hode

  摘要：

  Chiral E-enals derived from functionalized 2-deoxy-D-ribofuranoses by ylide-induced beta-elimination were exploited for the synthesis of fatty acid metabolites containing the (R)-hydroxy-E,Z-diene subunit.

  DOI：

  10.1016/s0040-4039(00)79912-6
• 作为产物：
  描述：

  2-deoxy-D-ribose 在 吡啶 、 硫酸 作用下， 反应 34.0h， 生成 methyl 2-deoxy-3,5-di-O-p-toluenesulfonyl-D-erythro-pentofuranoside
  参考文献：
  名称：

  Synthesis of Different 3,5‐Diazidofuranoses: A New and General Synthesis Pathway

  摘要：

  Diamino- and diazidofuranoses represent useful precursors, for example, for the synthesis of substituted nucleosides and metal complexes, respectively. Known procedures for their synthesis lack the availability of cheap starting materials, adequate yields, and the access to all possible diastereomeres. Therefore, 3,5-diazido-3,5-dideoxy- and - 2,3,5- trideoxyfuranoses both with ribo- and xylo- configuration were prepared using different approaches.

  DOI：

  10.1080/07328300701540175

文献信息

• Synthetic approaches to a chiral 4-amino-3-hydroxy piperidine with pharmaceutical relevance
  作者：Adrian Ortiz、Ian S. Young、James R. Sawyer、Yi Hsiao、Amarjit Singh、Masano Sugiyama、R. Michael Corbett、Melissa Chau、Zhongping Shi、David A. Conlon

  DOI：10.1039/c2ob25411e

  日期：——

  strategies were evaluated towards the preparation of (−)-(3R,4R)-1-benzyl-4-(benzylamino)piperidin-3-ol (1), which was constructed with control over the relative and absolute stereochemistry of the 4,3-amino alcohol moiety. The first strategy employed a novel RhI catalyzed asymmetric hydrogenation, while two other strategies exploited the existing stereochemistry in 2-deoxy-D-ribose, and the fourth explored

  评估了四种综合策略来制备甲壳素。 （-）-（3 R，4 R）-1-苄基-4-（苄基氨基）哌啶-3-醇（1），其是通过控制4，3-氨基醇部分的相对和绝对立体化学而构建的。第一种策略采用了新型的Rh I催化的不对称氢化反应，而另外两种策略则采用了现有的立体化学方法。2-脱氧-D-核糖，和第四次探索生物催化和古典拆分技术作为一种手段赋予对映体中间体途径到目标结构（-）- 1对映体富集。
• 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.
• 339. Deoxy-sugars. Part XIX. The conversion of D-arabinose into 3-deoxy-D-xylose derivatives
  作者：R. Allerton、W. G. Overend

  DOI：10.1039/jr9510001480

  日期：——
• Synthesis of Different 3,5‐Diazidofuranoses: A New and General Synthesis Pathway
  作者：Daniel Koth、Andrea Fiedler、Sandy Scholz、Michael Gottschaldt

  DOI：10.1080/07328300701540175

  日期：2007.9

  Diamino- and diazidofuranoses represent useful precursors, for example, for the synthesis of substituted nucleosides and metal complexes, respectively. Known procedures for their synthesis lack the availability of cheap starting materials, adequate yields, and the access to all possible diastereomeres. Therefore, 3,5-diazido-3,5-dideoxy- and - 2,3,5- trideoxyfuranoses both with ribo- and xylo- configuration were prepared using different approaches.
• A concise synthesis of (R)-hydroxy-E,Z-diene fatty acids: preparation of 12(R)-hete, tetranor-12(R)-hete, and 13(R)-hode
  作者：Sun Lumin、J.R. Falck、Michal L. Schwartzman

  DOI：10.1016/s0040-4039(00)79912-6

  日期：1991.5

  Chiral E-enals derived from functionalized 2-deoxy-D-ribofuranoses by ylide-induced beta-elimination were exploited for the synthesis of fatty acid metabolites containing the (R)-hydroxy-E,Z-diene subunit.