methyl (methyl 3-deoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate | 76836-15-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (methyl 3-deoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate
• 英文别名: methyl (2R,4S,5R,6R)-4,5-dihydroxy-2-methoxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
• CAS: 76836-15-2
• 化学式: C₁₁H₂₀O₉
• 分子量: 296.274
• InChiKey: ONBAYYSFFLRVTL-YRMXFSIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  146
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl (methyl 3-deoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate 在 palladium on activated charcoal 4-二甲氨基吡啶 、 叠氮基三甲基硅烷 、 偶氮二甲酸二异丙酯 、 氢气 、 溶剂黄146 、 三乙胺 、 三苯基膦 作用下， 以 吡啶 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， -70.0~20.0 ℃ 、344.74 kPa 条件下， 反应 172.58h， 生成 methyl (methyl 4,5,7,8-tetra-O-acetyl-9-benzamido-3,9-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate
  参考文献：
  名称：

  THE SYNTHESIS OF C-9 MODIFIED DERIVATIVES OF THE α-METHYL GLYCOSIDE OF KDN METHYL ESTER

  摘要：

  The synthesis of a range of C-9 substituted derivatives of the cc-methyl glycoside of KDN methyl ester (2) is reported. 9-Deoxy-9-iodo, 9-deoxy-9 thioacetyl and 9-azido-9-deoxy derivatives (compounds 10, 12 and 13) were all prepared from the corresponding 9-O-tosylate 8. Catalytic hydrogenation of 10 and 13 results in reduction to give the 9-deoxy and 9-amino-9-deoxy derivatives 20 and 15, respectively. Further derivatisation of the amine 15 into compounds 17 and 18 was achieved via standard acylation procedures.

  DOI：

  10.1081/car-100103960
• 作为产物：
  描述：

  methyl (methyl 4,5,7,8,9-penta-O-acetyl-3-deoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate 在 甲醇 、 potassium carbonate 作用下， 反应 1.0h， 以100%的产率得到methyl (methyl 3-deoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate
  参考文献：
  名称：

  Studies on Sialic Acid. Part XXVII. Synthesis and Characterization of Furanose and Pyranose Derivatives of 3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid (KDN).

  摘要：

  3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN)的费舍尔甲基糖基化产物表明，KDN 的 α, β-呋喃糖和 α, β-吡喃糖之间存在着异构体平衡。尽管存在同分异构平衡，但用乙酸酐与吡啶对 KDN 及其衍生物进行过乙酰化反应只能得到 α 和 β-吡喃糖衍生物。获得的甲基苷和六-O-乙酰基衍生物通过 X 射线、核磁共振和立体二色光谱分析进行了表征。

  DOI：

  10.1248/cpb.40.879

文献信息

• Reaction Products from Fischer's Methylation of 3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid (KDN).
  作者：Toshitsugu KAI、Xue-Long SUN、Makoto TANAKA、Hiroaki TAKAYANAGI、Kimio FURUHATA

  DOI：10.1248/cpb.44.208

  日期：——

  Several compounds were isolated from the Fischer's methylation reaction mixture of 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) with hydrochloric acid or methanesulfonic acid in methanol. The major product was methyl (methyl 3-deoxy-β-D-glycero-D-galacto-2-nonulopyranosid)onate (2), which we have already reported. New furan derivatives and a 4, 8-anhydro product were also isolated. The structures of these compounds were elucidated by nuclear magnetic resonance spectroscopy and X-ray crystallographic analysis.

  从 3-脱氧-D-甘油-D-半乳糖-2-壬磺酸（KDN）与盐酸或甲磺酸在甲醇中的费歇尔甲基化反应混合物中分离出了几种化合物。主要产物是 3-脱氧-β-D-甘油-D-半乳糖-2-壬磺吡喃糖酸甲酯（2），我们已经对此进行了报道。此外，还分离出了新的呋喃衍生物和一种 4，8-脱氢产物。这些化合物的结构是通过核磁共振光谱和 X 射线晶体分析法阐明的。
• Oxidation Products of C-4 and C-7 Hydroxyls in the Methyl α-Glycoside Derivatives of KDN¹
  作者：Toshitsugu Kai、Xue-Long Sun、Hiroaki Takayanagi、Kimio Furuhata

  DOI：10.1080/07328309708007332

  日期：1997.5

  A regioselective protection of hydroxyl groups in the methyl ester-methyl alpha-glycoside derivative of KDN was demonstrated. Isopropylidenation of methyl (methyl 3-deoxy-alpha-D-glycero-D-galacto-2-nonulopyranosid)onate (1) gave mono- (8,9) and di- (5,7:8,9) O-isopropylidene derivatives. Benzoylation of methyl (methyl 3-deoxy-8, 9-O-isopropylidene-alpha-D-glycero-D-galacto-2 -nonulopyranosid)onate (7) gave di- (4,5) and tri- (4,5,7) O-benzoates. Through these reactions, it was found that the reactivity of the hydroxyl groups was different from that of methyl beta-glycoside of KDN. Oxidation products of C-4 and C-7 hydroxyl groups (6 and 11) were synthesized from these compounds.