methyl β-2-deoxy-L-ribopyranoside | 26528-46-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl β-2-deoxy-L-ribopyranoside
• 英文别名: Methyl-2-deoxy-α-L-erythro-pentopyranosid；methyl-(α-L-erythro-2-deoxy-pentopyranoside)；Methyl-(α-L-erythro-2-desoxy-pentopyranosid)；(3S,4R,6R)-6-methoxyoxane-3,4-diol
• CAS: 26528-46-1
• 化学式: C₆H₁₂O₄
• 分子量: 148.159
• InChiKey: CYLGOSOYSUHPCY-NGJCXOISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl β-2-deoxy-L-ribopyranoside 在 吡啶 、 盐酸 、 aluminum oxide 、 四(三苯基膦)钯 、 三丁基氯化锡 、 叔丁基锂 、 sodium cyanoborohydride 、 silver nitrate 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 pyridinium chlorochromate 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 19.5h， 生成
  参考文献：
  名称：

  3-Hydroxyleukotriene B4 (3-OH-LTB4): Total Synthesis and Stereochemical Assignment.

  摘要：

  The asymmetric total synthesis of 3-hydroxyleukotriene B-4 (3-OH-LTB(4)), an ethanol-inducible proinflammatory autacoid, was achieved using a triply convergent strategy for the sequential union of propargylic arsonium salt 3 with pyranosides 2a,b and furanose 4. Both saccharide subunits were derived from commercial 2-deoxy-D-ribose. The key transformation involved palladium-mediated coupling of bromoacetylenide 9 with stannylglycal 6a,b. Subsequent Rieke zinc hydrogenation of acetylene 10a,b and controlled ionic reduction of the cross-conjugated cyclic enol ether using NaBH3CN at pH similar to 4-4.5 established the cis-Delta(6,7)-olefin and C(5)-hydroxyl stereochemistry, respectively, and led to 11a,b. Methyllactol hydrolysis, PCC oxidation, methanolysis, and desilylation afforded 3(R)- and 3(S)-OH-LTB(4) methyl esters, respectively. On the basis of chromatographic and mass spectral comparisons, enzymatically derived 3-OH-LTB(4) is composed principally of the 3(S)-isomer (>95%).

  DOI：

  10.1021/ja00091a004
• 作为产物：
  描述：

  [(2R,4S,5R)-2-methoxy-5-(4-nitrobenzoyl)oxyoxan-4-yl] 4-nitrobenzoate 在 sodium methylate 作用下， 反应 1.0h， 以90%的产率得到methyl β-2-deoxy-L-ribopyranoside
  参考文献：
  名称：

  3-Hydroxyleukotriene B4 (3-OH-LTB4): Total Synthesis and Stereochemical Assignment.

  摘要：

  The asymmetric total synthesis of 3-hydroxyleukotriene B-4 (3-OH-LTB(4)), an ethanol-inducible proinflammatory autacoid, was achieved using a triply convergent strategy for the sequential union of propargylic arsonium salt 3 with pyranosides 2a,b and furanose 4. Both saccharide subunits were derived from commercial 2-deoxy-D-ribose. The key transformation involved palladium-mediated coupling of bromoacetylenide 9 with stannylglycal 6a,b. Subsequent Rieke zinc hydrogenation of acetylene 10a,b and controlled ionic reduction of the cross-conjugated cyclic enol ether using NaBH3CN at pH similar to 4-4.5 established the cis-Delta(6,7)-olefin and C(5)-hydroxyl stereochemistry, respectively, and led to 11a,b. Methyllactol hydrolysis, PCC oxidation, methanolysis, and desilylation afforded 3(R)- and 3(S)-OH-LTB(4) methyl esters, respectively. On the basis of chromatographic and mass spectral comparisons, enzymatically derived 3-OH-LTB(4) is composed principally of the 3(S)-isomer (>95%).

  DOI：

  10.1021/ja00091a004

文献信息

• Monocyclic L-nucleosides, analogs and uses thereof
  申请人：——

  公开号：US20030018186A1

  公开（公告）日：2003-01-23

  Novel monocyclic L-Nucleoside compounds have the general formula 1 Embodiments of these compounds are contemplated to be useful in treating a wide variety of diseases including infections, infestations, neoplasms, and autoimmune diseases. Viewed in terms of mechanism, embodiments of the novel compounds show immunomodulatory activity, and are expected to be useful in modulating the cytokine pattern, including modulation of Th1 and Th2 response.

  新型单环L-核苷化合物的一般式为1。这些化合物的实施形式被认为对治疗各种疾病有用，包括感染、寄生虫感染、肿瘤和自身免疫性疾病。从机制上看，这些新型化合物的实施形式显示出免疫调节活性，并有望用于调节细胞因子模式，包括调节Th1和Th2反应。
• Deriaz et al., Journal of the Chemical Society, 1949, p. 2836,2839
  作者：Deriaz et al.

  DOI：——

  日期：——
• US6130326A
  申请人：——

  公开号：US6130326A

  公开（公告）日：2000-10-10
• US6552183B1
  申请人：——

  公开号：US6552183B1

  公开（公告）日：2003-04-22
• US6573248B2
  申请人：——

  公开号：US6573248B2

  公开（公告）日：2003-06-03