methyl 5-amino-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosidonic acid | 140446-10-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 5-amino-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosidonic acid
• 英文别名: methyl 5-amino-3,5-dideoxy-2-thio-α-D-glycero-D-galacto-2-nonulopyranosonic acid；Neu(a)-SMe；(2S,4S,5R,6R)-5-amino-4-hydroxy-2-methylsulfanyl-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 140446-10-2
• 化学式: C₁₀H₁₉NO₇S
• 分子量: 297.329
• InChiKey: LRNGKMLDVJXYCI-APDUKXCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  179
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 5-amino-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosidonic acid 在 吡啶 、 sodium hydroxide 、 3 A molecular sieve 、 caesium carbonate 、 DMTST 、 三乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 56.0h， 生成 2,7-anhydro-5-N-glycolyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosonic acid
  参考文献：
  名称：

  Studies on Sialic Acids. XXX. Synthesis of 2,7-Anhydrosialic Acid.

  摘要：

  以 5-acetamido-3, 5-dideoxy-2-thio-α-D-glycero-D-galacto-2-nonulopyranosonate 甲酯为原料，高产率合成了 N-乙酰基-和 N-乙醇酰基-2, 7-脱水神经氨酸。通过 1H-NMR 谱和 X 射线晶体分析阐明了这些聚糖唾液酸的结构和立体化学。 N-乙酰基-和N-乙醇酰-2, 7-脱水神经氨酸（1和10）的环系统被确定具有相同的2C5(D)构象。

  DOI：

  10.1248/cpb.40.3197
• 作为产物：
  描述：

  methyl (methyl 5-acetamido-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate 在 barium dihydroxide 作用下， 反应 15.0h， 以85%的产率得到methyl 5-amino-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosidonic acid
  参考文献：
  名称：

  Studies on Sialic Acids. XXX. Synthesis of 2,7-Anhydrosialic Acid.

  摘要：

  以 5-acetamido-3, 5-dideoxy-2-thio-α-D-glycero-D-galacto-2-nonulopyranosonate 甲酯为原料，高产率合成了 N-乙酰基-和 N-乙醇酰基-2, 7-脱水神经氨酸。通过 1H-NMR 谱和 X 射线晶体分析阐明了这些聚糖唾液酸的结构和立体化学。 N-乙酰基-和N-乙醇酰-2, 7-脱水神经氨酸（1和10）的环系统被确定具有相同的2C5(D)构象。

  DOI：

  10.1248/cpb.40.3197

文献信息

• Total synthesis of a modified ganglioside, de-N-acetyl GM2
  作者：Shuji Fujita、Masaaki Numata、Mamoru Sugimoto、Kenkichi Tomita、Tomoya Ogawa

  DOI：10.1016/0008-6215(94)00155-3

  日期：1994.10

  into imidates 25 and 26, coupling with (2S,3R,4E)-3-O-benzoyl-2-N-tetracosanoylsphingenine (2) was executed to afford completely protected ganglioside analogues 27 and 28. Selective cleavage of the methyl ester and N,O-deprotection gave the target de-N-acetyl GM2 (1).

  进行在C-5处带有N-邻苯二甲酰基保护基的唾液酰基供体6的区域和立体选择性糖基化，在O-2a处带有带有新戊酰基的乳糖基受体7，得到预期的糖三​​糖苷5。 5与2-叠氮基半乳糖基供体4一起得到糖四糖基衍生物18和19。在将18转化成酰亚胺25和26之后，与（2S，3R，4E）-3-O-苯甲酰基-2-N-四椰酰基鞘氨醇（2）偶联。制备完全保护的神经节苷脂类似物27和28。甲酯的选择性裂解和N，O-去保护得到目标脱-N-乙酰基GM2（1）。
• Synthesis of 5-N- and 9-N-thioacylated sialic acids
  作者：Rainer Isecke、Reinhard Brossmer

  DOI：10.1016/s0040-4020(01)90473-9

  日期：——

  N-Thioacylation of neuraminic acid methyl alpha-glycoside (5) with O-ethyl thioformate (1), methyl dithioacetate (2), and methyl dithiopropionate (3) afforded N-thioformyl, N-thioacetyl, and N-thiopropionyl neuraminic acid derivatives 6a-c in high yield. Cleavage of the glycosides was accomplished either by acid hydrolysis or by sialidase treatment. Alternatively, 5-N-thioacylneuraminic acids were produced from the corresponding N-thioacyl-D-mannosamines 7a-c and pyruvate employing N-acetylneuraminate pyruvate lyase. The sialidase-resistant methyl alpha-thioglycoside of N-thioacetylneuraminic acid (10) was also prepared. N-Acetyl-9-deoxy-9-thioacetamido neuraminic acid (19) was obtained either directly by reaction of N-acetyl-9-amino-9-deoxyneuraminic acid (17) with methyl dithioacetate (2) or via its methyl alpha-glycoside 18. Compound 17 was produced from the methyl a-glycoside of 9-O-tosylated methyl ester 12 via the azide 13. -For the 5-N-thioacyl sialic acids 6a-c and 8a-c as well as for the 9-deoxy-9-thioacetamido derivatives 18 and 19 some biological properties are reported.
• Total synthesis of the modified ganglioside de -N-acetyl-GM3 and some analogs
  作者：Shuji Fujita、Masaaki Numata、Mamoru Sugimoto、Kenkichi Tomita、Tomoya Ogawa

  DOI：10.1016/0008-6215(92)84130-k

  日期：1992.4

  corresponding glycotriosyl donors which, upon coupling with (2S,3R,4E)-3-O-benzoyl-2-N-tetracosanoylsphingenine, afforded completely protected ganglioside analogs 39, 40, and 41, respectively. Deprotection of 40, 41, and 39 completed the synthesis of the modified ganglioside de-N-acetyl-GM3, a stereoisomer, and a regioisomer. The N-deprotected forms of 40 and 39, on successive treatment with methyl isocyanate

  分别伴有β-连接的异构体22和19。将化合物18、21和22转化为相应的糖三糖基供体，其与（2S，3R，4E）-3-O-苯甲酰基-2-N-四二十烷酰基鞘氨醇偶联后，得到完全保护的神经节苷脂类似物39、40和41。 ， 分别。40、41和39的脱保护完成了修饰的神经节苷脂de-N-乙酰基-GM3，立体异构体和区域异构体的合成。依次用异氰酸甲酯和O-去保护的N-脱保护形式的40和39，得到了GM3的N-（N-甲基氨基甲酰基）类似物及其区域异构体。分别。40、41和39的脱保护完成了修饰的神经节苷脂de-N-乙酰基-GM3，立体异构体和区域异构体的合成。依次用异氰酸甲酯和O-去保护的N-脱保护形式的40和39，得到了GM3的N-（N-甲基氨基甲酰基）类似物及其区域异构体。分别。40、41和39的脱保护完成了修饰的神经节苷脂de-N-乙酰基-GM3，立体异构体和区域异构体的合成。依次用异氰酸甲酯和
• Studies on Sialic Acids. XXX. Synthesis of 2,7-Anhydrosialic Acid.
  作者：Kimio FURUHATA、Haruo OGURA

  DOI：10.1248/cpb.40.3197

  日期：——

  N-Acetyl-and N-glycolyl-2, 7-anhydroneuraminic acid were synthesized from methyl 5-acetamido-3, 5-dideoxy-2-thio-α-D-glycero-D-galacto-2-nonulopyranosonate in high yield. The structures and stereochemistry of these glycosanic sialic acids were elucidated from 1H-NMR spectra and X-ray crystal analysis. The ring systems of N-acetyl- and N-glycolyl-2, 7-anhydroneuraminic acid (1 and 10) were determined to have the same 2C5(D) conformation.

  以 5-acetamido-3, 5-dideoxy-2-thio-α-D-glycero-D-galacto-2-nonulopyranosonate 甲酯为原料，高产率合成了 N-乙酰基-和 N-乙醇酰基-2, 7-脱水神经氨酸。通过 1H-NMR 谱和 X 射线晶体分析阐明了这些聚糖唾液酸的结构和立体化学。 N-乙酰基-和N-乙醇酰-2, 7-脱水神经氨酸（1和10）的环系统被确定具有相同的2C5(D)构象。