methyl 2,6-anhydro-3-deoxy-D-glycero-D-galacto-non-2-enonate | 259678-92-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2,6-anhydro-3-deoxy-D-glycero-D-galacto-non-2-enonate
• 英文别名: methyl (2R,3R,4S)-3,4-dihydroxy-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylate
• CAS: 259678-92-7
• 化学式: C₁₀H₁₆O₈
• 分子量: 264.232
• InChiKey: NFWYRVJWUYPJGI-FVDCJOIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  137
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2,6-anhydro-3-deoxy-D-glycero-D-galacto-non-2-enonate 在 吡啶 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 84.0h， 生成 methyl 2,6-anhydro-3,9-dideoxy-9-iodo-D-glycero-D-galacto-non-2-enoate
  参考文献：
  名称：

  KDN2EN甲基酯的一些C-4和C-9取代衍生物的合成

  摘要：

  报道了KDN2en甲酯2的许多C-4和C-9取代的衍生物的合成。9-脱氧-9-碘，9-叠氮基-9-脱氧和9- ö甲基的衍生物2（化合物5，7和9由相应的9-制备）ø -tosylate，2,6-脱水- 3-脱氧-9- ø - p -toluenesulfonyl- d -甘油基- d -半乳-壬-2- enonate（3）。这些化合物已被充分表征为过乙6，8和10。用KSAc处理3得到9-硫代乙酰基衍生物，其被分离为过乙酸盐11。4- Ç -乙烯基-4-脱氧（14），4- Ç苯基4-脱氧（15）和4- Ç - [1-（甲氧基羰基）乙烯基] -4-脱氧（16）的衍生物2中制备通过钯催化的4-耦合外延-氯化物，甲基5,7,8,9-四- ø -乙酰基-2,6-脱水-4-氯-3,4-二脱氧d -甘油基- d -距骨-壬-2- enonate（12）与适当的有机锡烷。

  DOI：

  10.1081/car-100108270
• 作为产物：
  描述：

  methyl (2,4,5,7,8,9-hexa-O-acetyl-3-deoxy-D-glycero-β-D-galacto-2-nonulopyran-ose)onate 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 methyl 2,6-anhydro-3-deoxy-D-glycero-D-galacto-non-2-enonate
  参考文献：
  名称：

  2,3-Didehydro-2-deoxysialic acids structurally varied at C-5 and their behaviour towards the sialidase from Vibrio cholerae

  摘要：

  2,3-Didehydro-2-deoxy-N-trifluoroacetylneuraminic acid (5-trifluoroacetyl-Neu2en) (3) has been synthesised from Neu5Ac2en (1) by hydrazinolysis, to give Neu2en (2), followed by N-trifluoroacetylation. 2,3-Didehydro-2,3-dideoxy-D-glycero-D-galacto-2-nonulopyranoson ic acid (Kdn2en, 8) and 5-azido-2,3-didehydro-2,3,5-trideoxy-D-glycero-D-galacto-2-nonu lopyranosonic acid (5-azido-5-deoxy-Kdn2en, 9) have been prepared from the acetylated methyl esters of Kdn (4) and 5-azido-5-deoxy-Kdn (5) via Zemplén saponification. The behaviour of the above 2,3-didehydro-2-deoxysialic acids towards Vibrio cholerae sialidase has been investigated.

  DOI：

  10.1016/0008-6215(92)84150-q

文献信息

• Synthesis of 4-Oxo and 4-Hydroxyimino-4-Deoxy-Kdn2En Derivatives
  作者：Xue-Long Sun、Toshitsugu Kai、Noriko Sato、Hiroaki Takayanagi、Kimio Furuhata

  DOI：10.1080/07328309908544060

  日期：1999.1

  2,6-Anhydro-3-deoxy-D-manno-non-2-en-4-ulsonic acid (4-oxo-Kdn2en, 2) was synthesized from methyl 2,6-anhydro-3-deoxy-D-glycero-D-galacto-non-2-enonate (Kdn-2en methyl ester, 7) by the oxidation with manganese dioxide in dry acetone in good yield. 4-Hydroxyimino-Kdn2en derivatives(3), and 4-carbethoxymethylene-Kdn2en derivatives (4) were synthesized from the peracetylated methyl ester of 4-oxo-Kdn2en by oximation and Wittig reaction in good yield, respectively.
• 2,3-Didehydro-2-deoxysialic acids structurally varied at C-5 and their behaviour towards the sialidase from Vibrio cholerae
  作者：Erwin Schreiner、Erich Zbiral、Reinhard G. Kleineidam、Roland Schauer

  DOI：10.1016/0008-6215(92)84150-q

  日期：1992.9

  2,3-Didehydro-2-deoxy-N-trifluoroacetylneuraminic acid (5-trifluoroacetyl-Neu2en) (3) has been synthesised from Neu5Ac2en (1) by hydrazinolysis, to give Neu2en (2), followed by N-trifluoroacetylation. 2,3-Didehydro-2,3-dideoxy-D-glycero-D-galacto-2-nonulopyranoson ic acid (Kdn2en, 8) and 5-azido-2,3-didehydro-2,3,5-trideoxy-D-glycero-D-galacto-2-nonu lopyranosonic acid (5-azido-5-deoxy-Kdn2en, 9) have been prepared from the acetylated methyl esters of Kdn (4) and 5-azido-5-deoxy-Kdn (5) via Zemplén saponification. The behaviour of the above 2,3-didehydro-2-deoxysialic acids towards Vibrio cholerae sialidase has been investigated.
• THE SYNTHESIS OF SOME C-4 AND C-9 SUBSTITUTED DERIVATIVES OF KDN2EN METHYL ESTER
  作者：Adele Norton、Gaik Kok、Mark Itzstein

  DOI：10.1081/car-100108270

  日期：——

  and 10. Treatment of 3 with KSAc gave the 9-thioacetyl derivative which was isolated as the peracetate 11. 4-C-Ethenyl-4-deoxy (14), 4-C-phenyl-4-deoxy (15) and 4-C-[1-(methoxycarbonyl)ethenyl]-4-deoxy (16) derivatives of 2were prepared via the palladium-catalysed coupling of the 4-epi-chloride, methyl 5,7,8,9-tetra-O-acetyl-2,6-anhydro-4-chloro-3,4-dideoxy-D-glycero-D-talo-non-2-enonate (12) with the

  报道了KDN2en甲酯2的许多C-4和C-9取代的衍生物的合成。9-脱氧-9-碘，9-叠氮基-9-脱氧和9- ö甲基的衍生物2（化合物5，7和9由相应的9-制备）ø -tosylate，2,6-脱水- 3-脱氧-9- ø - p -toluenesulfonyl- d -甘油基- d -半乳-壬-2- enonate（3）。这些化合物已被充分表征为过乙6，8和10。用KSAc处理3得到9-硫代乙酰基衍生物，其被分离为过乙酸盐11。4- Ç -乙烯基-4-脱氧（14），4- Ç苯基4-脱氧（15）和4- Ç - [1-（甲氧基羰基）乙烯基] -4-脱氧（16）的衍生物2中制备通过钯催化的4-耦合外延-氯化物，甲基5,7,8,9-四- ø -乙酰基-2,6-脱水-4-氯-3,4-二脱氧d -甘油基- d -距骨-壬-2- enonate（12）与适当的有机锡烷。