6-hydroxy-6-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyran-3(2H,6H)-one | 121701-32-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-hydroxy-6-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyran-3(2H,6H)-one
• 英文别名: 6-hydroxy-6-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2H-pyran-3(6H)-one；6-hydroxy-6-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2,6-dihydropyran-3-one；6-hydroxy-6-(2,3,5-tri-O-benzoyl-beta-d-ribofuranosyl)-2h-pyran-3-one；[(2R,3R,4R,5R)-3,4-dibenzoyloxy-5-(2-hydroxy-5-oxopyran-2-yl)oxolan-2-yl]methyl benzoate
• CAS: 121701-32-4
• 化学式: C₃₁H₂₆O₁₀
• 分子量: 558.541
• InChiKey: OHFYEOYEEDAQCL-FRNXGWJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  135
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  6-hydroxy-6-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyran-3(2H,6H)-one 在 盐酸 、 盐酸羟胺 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 甲醇 、 溶剂黄146 为溶剂， 反应 6.34h， 生成 (Z)-2-amino-5-hydroxyiminomethyl-7-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyrrolo[2,1-f][1,2,4]triazine
  参考文献：
  名称：

  吡咯并[2,1-f] [1,2,4]三嗪C-核苷的合成。桑格霉素，结核菌素和玩具霉素的同分异构体

  摘要：

  报道了吡咯并[2,1-f] [1,2,4]三嗪C-核苷的合成。用氨基胍在乙酸中处理吡喃糖苷，以96％的收率得到相应的半卡巴zone。半卡巴zone在二恶烷中的环转化提供了51％的2-氨基-7-（2,3,5-三-O-苯甲酰基-β-D-呋喃呋喃糖基）吡咯并[2,1-f]-[1]收率，2,4]三嗪。吡咯并三嗪的维尔斯迈尔甲酰化反应以69％的收率得到了主要产物5-甲酰基吡咯并[2,1-f] [1,2,4]三嗪。用甲醇中的盐酸羟胺处理醛，得到醛肟。用三氟甲磺酸酐和三乙胺在二氯甲烷中使醛肟肟脱水，得到5-氰基吡咯并[2,1-f] [1,2,4]三嗪，产率为44％。腈转化为脱保护的酰胺2-氨基-7-（β-D-呋喃呋喃糖基）吡咯并[2,1-f] [1,2,4]三嗪-5-甲酰胺，在室温下用30％H2O2的乙醇溶液处理1天，可实现96％的收率。用氢氧化钠溶液脱苯甲酰化产生脱保护的C-核苷。

  DOI：

  10.1016/s0008-6215(01)00017-9
• 作为产物：
  描述：

  5-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2-furfuryl alcohol 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以72%的产率得到6-hydroxy-6-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)pyran-3(2H,6H)-one
  参考文献：
  名称：

  C-nucleosides. 7. Preparation and utility of 6-hydroxy-6-(2,3,5-tri-O-benzoyl-.beta.-D-ribofuranosyl)-2H-pyran-3(6H)-one as a key intermediate of C-nucleoside synthesis

  摘要：

  DOI：

  10.1021/jo00242a012

文献信息

• Synthesis of 5-hydroxy-2-(β-d-ribofuranosyl)pyran-4-one from a pyranulose glycoside
  作者：Shigeyuki Kanazawa、Souhei Mizuno、Rie Yamauchi、Natsu Nishimura、Isamu Maeba

  DOI：10.1016/s0008-6215(99)00098-1

  日期：1999.5

  trifluoroacetic acid (TFA) in dioxane afforded a mixture of 5-hydroxy-2-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)pyran-4-one (3) and its furan derivative 5-hydroxy-2-5-(benzoyloxy)methyl]furan-2-yl}pyran-4-one (4), but the use of hydrochloric acid formed the bromofurfural, 3-bromo-5-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-2-furancarboxyal dehyde only. Acetylation of a mixture (3 and 4) with acetic anhydride

  描述了5-羟基-2-（β-D-呋喃呋喃糖基）吡喃-4-酮（9）的合成。在四氯化碳中用溴处理吡喃糖苷得到溴吡喃糖苷，收率为90％。（6S）-和（6R）-4-溴-6-羟基-6-（2,3,5-三-O-苯甲酰基-β-D-呋喃呋喃糖基）-6H-吡喃-3-酮的反应（ 2）在酸性介质中检查具有以下结果：2与三氟乙酸（TFA）在二恶烷中的反应提供了5-羟基-2-（2,3,5-三-O-苯甲酰基-β-D的混合物-核呋喃糖基）吡喃-4-酮（3）及其呋喃衍生物5-羟基-2- 5-（苯甲酰氧基）甲基]呋喃-2-基}吡喃-4-酮（4），但使用盐酸仅形成了溴糠醛，3-溴-5-（2,3,5-三-O-苯甲酰基-β-D-呋喃呋喃糖基）-2-呋喃羧基醛。混合物（3和4）与乙酸酐的乙酰化促进产物分离，得到相应的乙酸酯5-乙酰氧基-2-（2,3,5-三-O-苯甲酰基-β-D-呋喃呋喃糖基）吡喃-4-酮（5）和5-乙酰氧基-2-
• Synthesis of a ‘direct-linked’ C-disaccharide from a pyranulose glycoside
  作者：Misa Yuasa、Shigeyuki Kanazawa、Natsu Nishimura、Taeko Higuchi、Isamu Maeba

  DOI：10.1016/s0008-6215(98)00307-3

  日期：1999.1

  The absolute stereochemistry of each was determined from its CD spectrum. The reduction of 2a with NaBH4 in methanol afforded two allylic alcohols 6a and 6b in 14 and 73% yield, respectively. The reduction of 2b with NaBH4 afforded 6c and 6d in 30 and 56% yield, respectively. Cis hydroxylation of the double bond in compounds 6a–d with osmium tetroxide gave 7a–e. The stereoisomers 7a–e were separated and

  摘要报道了五种“直接连接”的C-二糖8a-e的合成。吡喃糖苷1的（Et3SiH / BF3·Et2O）还原生成（6S）-和（6R）-6-（2,3,5-三-O-苯甲酰基-β-d-核呋喃呋喃糖基）吡喃-3（2H， 6H）-一个（2a和2b）的比例为ca. 2：1，总收率达88％。从其CD光谱确定每个的绝对立体化学。用NaBH4在甲醇中还原2a，得到两种烯丙基醇6a和6b，产率分别为14％和73％。用NaBH4还原2b分别得到6c和6d，产率分别为30％和56％。化合物6a-d与四氧化的双键的顺式羟基化反应得到7a-e。分离了立体异构体7a–e，并通过1H NMR光谱确定了它们的构型。用碳酸钠水溶液对化合物7a-e进行脱苯甲酰化可生成脱保护的C-二糖8a-e。
• C-nucleosides. 10. Synthesis of 1,3-dimethyl-7-(.beta.-D-ribofuranosyl)lumazine
  作者：Isamu Maeba、Kazuhiro Kitaori、Chihiro Ito

  DOI：10.1021/jo00277a033

  日期：1989.8
• A Novel Synthesis of C-Nucleosides Having Pyrrolo[1,2-f]pteridine, 6- and 8-Deazapyrrolo[1,2-f]pteridine Ring Systems from 6-Hydroxy-6-(2,3,5-tri-O-benzoyl-b-D-ribofuranosyl)-2H-pyran-3(6H)-one
  作者：Isamu Maeba、Natsu Nishimura、Yoshitada Hasegawa、Souhei Mizuno、Misa Yuasa

  DOI：10.3987/com-98-8313

  日期：——
• C-Nucleosides. 15. Novel Ring Transformation of 6-Hydroxy-6-(2,3,5-tri-O-benzoyl-b-D-ribofuranosyl)-2,6-dihydropyran-3-one with Amidines to Imidazole
  作者：Isamu Maeba、Kazuya Osaka、Chihiro Ito

  DOI：10.3987/com-90-5615

  日期：——

  The novel ring transformation of 6-hydroxy-6-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)-2,6-dihydropyran-3-one (1) with amidines to imidazole is described. Treatment of 1 with benzamidine afforded 3-[2-phenyl-4-(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl)imidazolyl]-2-oxo-1-propanol (2) in 53% yield. H-1 and C-13 nmr spectra of 2 accounted for the contribution of tautomeric structure. Deprotection of 2 with methanolic sodium hydroxide afforded 3-[2-phenyl-4-(beta-D-ribofuranosyl)imidazolyl]-2-oxo-1-propanol (5) in 35% yield. Treatment of 1 with O-methylisourea afforded 2-methoxyimidazole (3) in 27% yield. Treatment of 1 with acetamidine afforded 2-methylimidazole (4) in 10% yield. However, debenzoylation of 3 and 4 with alkaline did not afforded the deprotected imidazole C-nucleosides.