Methyl 2,4,5,7,8-penta-O-acetyl-3-deoxy-β-D-manno-oct-2-ulopyranosidonate | 104154-43-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 2,4,5,7,8-penta-O-acetyl-3-deoxy-β-D-manno-oct-2-ulopyranosidonate
• 英文别名: Methyl 2,4,5,7,8-penta-O-acetyl-3-deoxy-β-D-manno-2-octulopyranosonate；methyl 2,4,5,7,8-penta-O-acetyl-β-D-manno-octulosonate；methyl (2R,4R,5R,6R)-2,4,5-triacetyloxy-6-[(1R)-1,2-diacetyloxyethyl]oxane-2-carboxylate
• CAS: 104154-43-0
• 化学式: C₁₉H₂₆O₁₃
• 分子量: 462.408
• InChiKey: RKHXURDVRUYZFB-VDCDIQELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  32
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  167
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  methyl-4,5,7,8-tetra-O-acetyl-2,6-anhydro-2,3-dideoxy-D-manno-oct-2-enosonat 在 N-碘代丁二酰亚胺 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 19.0h， 生成 Methyl 2,4,5,7,8-penta-O-acetyl-3-deoxy-β-D-manno-oct-2-ulopyranosidonate
  参考文献：
  名称：

  Addition Reactions of Glycal Esters: Access to Glycosyl Donors of Kdo, d-glycero-d-talo- and d-glycero-d-galacto-2-Octulosonic Acid Residues

  摘要：

  Addition reactions of O-acetylated glycal esters of Kdo mono-, alpha-(2-->8)- and alpha(2-->4)- linked Kdo disaccharide derivatives 1a-c with NIS in acetic acid afforded good yields of trans-diaxial as well as minor amounts of trans-diequatorial and cis-configured 2-O-acetyl-3-deoxy-3-iodo derivatives, which were efficiently reduced with Bu(3)SnH/AIBN to give the corresponding per-O-acetylated Kdo methyl ester derivatives. Similar reactions of 1a with NBS or NCS furnished the trans-diaxial 2-O-acetyl-3-bromo-3-deoxy- as well as 3-chloro-3-deoxy derivatives as the main products. Reaction of 1a with NBS in aqueous MeCN provided the 2,3-trans-bromohydrin derivative 11c, which upon treatment with DBU in MeCN gave the elimination product 11 and the alpha-2,3-anhydro derivative 12 as a suitable donor of glycosides with D-glycero-D-talo- or D-glycero-D-galacto configuration, respectively.

  DOI：

  10.1080/07328309608005686

文献信息

• Synthesis of methyl pyranosides and furanosides of 3-deoxy-d-manno-oct-2-ulosonic acid (KDO) by acid-catalysed solvolysis of the acetylated derivatives
  作者：Paul A. McNicholas、Michael Batley、John W. Redmond

  DOI：10.1016/0008-6215(86)85041-8

  日期：1986.2

  Treatment of methyl 2,4,5,7,8-penta-O-acetyl-3-deoxy-alpha-D-manno-oct- 2-ulopyranosonic acid, or its methyl ester, with refluxing methanolic 0.1 M hydrogen chloride for 16 h gave 95% of methyl (methyl 3-deoxy-alpha-D-manno-oct-2-ulopyranosid)onate. Acetylation of the methyl ester of 3-deoxy-D-manno-oct-2-ulosonic acid (KDO) gave mainly methyl 2,4,6,7,8-penta-O-acetyl-3-deoxy-alpha,beta-D-manno-oct-2-ulofuranoso

  用回流的甲醇0.1 M氯化氢处理甲基2,4,5,7,8-戊基-O-乙酰基3-脱氧-α-D-甘露聚糖-辛基-2-氟吡喃磺酸或其甲酯h得到95％的甲基（3-脱氧-α-D-甘露聚糖-辛基-2-氟吡喃糖苷）甲基酸酯。3-脱氧-D-甘露聚糖-辛-2-磺酸的甲酯的乙酰化（KDO）主要产生甲基2,4,6,7,8-五-O-乙酰基-3-脱氧-α，β- D-甘露聚糖-oct-2-ulofuranoso。在室温下用0.02M甲醇的甲醇溶液处理该混合物，得到（3-脱氧-α，β-D-甘露辛基-辛-2-氟呋喃糖苷）甲基丙烯酸酯和相应的4-乙酸酯，其通过反相柱分离。的7,8-O-异亚丙基衍生物的色谱分析。通过乙酰化得到异亚丙基的位置，得到甲基（甲基4，6-二-O-乙酰基-3-脱氧-7，8-O-异亚丙基-α，β-D-甘露聚糖-oct-2-ul呋喃糖苷）。呋喃糖异构体的主要区别在于J3,4值（α约为6.1 Hz，β约为2.2
• IMOTO, MASAHIRO;KUSUMOTO, SHOICHI;SHIBA, TETSUO, TETRAHEDRON LETT., 28,(1987) N 49, 6235-6238
  作者：IMOTO, MASAHIRO、KUSUMOTO, SHOICHI、SHIBA, TETSUO

  DOI：——

  日期：——