(2R,3R,4R,5R,6R)-5-Acetoxy-4-acetylamino-3-bromo-2-methoxy-6-((1R,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester | 189143-89-3

• 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: (2R,3R,4R,5R,6R)-5-Acetoxy-4-acetylamino-3-bromo-2-methoxy-6-((1R,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS: 189143-89-3
• 化学式: C₂₁H₃₀BrNO₁₃
• 分子量: 584.372
• InChiKey: XZFRRFAVBFEBEK-CUAXDNIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.47
• 重原子数：
  36.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  179.06
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5R,6R)-5-Acetoxy-4-acetylamino-3-bromo-2-methoxy-6-((1R,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以87%的产率得到
  参考文献：
  名称：

  Syntheses of sialic acid analogues with acylamino groups at C-4 (N-acyl regioisomers of sialic acids)

  摘要：

  Methyl 5,7,8,9-tetra-O-acetyl-4-acylamino-2,6-anhydro-3,4-dideoxy-D-glycero-D-galacto- and D-talo-non-2-enonates were synthesized from the reaction of the peracetate of Kdn methyl ester with several nitriles in the presence of a Lewis acid. Treatment of these 2,4-dideoxy-4-acylamino-Kdn methyl esters with N-bromosuccinimide in methanol gave methyl (methyl 5,7,8,9-tetra-O-acetyl-4-acylamino-3-bromo-3,4-dideoxy-D-erythro-alpha-L-manno-non-2-ulopy-ranosid)onates (16, 18, and 20) and oxazine-type derivatives, 2-alkyl-(methyl 5,7,8,9-tetra-O-acetyl-3-bromo-3, 4-dideoxy-D-erythro-alpha-L-manno-non-2-ulopyranosonate)-5,6-dihydro-4H-1.3-oxazine (29, 30, and 31). Debromination of 16, 18, and 20 with Bu(3)SnH/AIBN in toluene gave methyl (methyl 5,7,8,9-tetra-O-acetyl-4-acylamino-3,4-dideoxy-beta-D-glycero-D-galacto-nonulopyranosid)onate (23, 24, and 25), whereas hydrolysis with HOAc and subsequent debromination with Bu(3)SnH/AIBN in toluene of 32 and 33 gave methyl 5,7,8,9-tetra-O-acetyl-4-acylamino-3,4-dideoxy-beta-D-glycero-D-talo-2-nonulopyranosonate (35 and 36) in the final step of the synthesis. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00302-3
• 作为产物：
  描述：

  methyl 5,7,8,9-tetra-O-acetyl-4-acetylamino-2,6-anhydro-3,4-dideoxy-D-glycero-D-galacto-non-2-enonate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以55%的产率得到(2R,3R,4R,5R,6R)-5-Acetoxy-4-acetylamino-3-bromo-2-methoxy-6-((1R,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Syntheses of sialic acid analogues with acylamino groups at C-4 (N-acyl regioisomers of sialic acids)

  摘要：

  Methyl 5,7,8,9-tetra-O-acetyl-4-acylamino-2,6-anhydro-3,4-dideoxy-D-glycero-D-galacto- and D-talo-non-2-enonates were synthesized from the reaction of the peracetate of Kdn methyl ester with several nitriles in the presence of a Lewis acid. Treatment of these 2,4-dideoxy-4-acylamino-Kdn methyl esters with N-bromosuccinimide in methanol gave methyl (methyl 5,7,8,9-tetra-O-acetyl-4-acylamino-3-bromo-3,4-dideoxy-D-erythro-alpha-L-manno-non-2-ulopy-ranosid)onates (16, 18, and 20) and oxazine-type derivatives, 2-alkyl-(methyl 5,7,8,9-tetra-O-acetyl-3-bromo-3, 4-dideoxy-D-erythro-alpha-L-manno-non-2-ulopyranosonate)-5,6-dihydro-4H-1.3-oxazine (29, 30, and 31). Debromination of 16, 18, and 20 with Bu(3)SnH/AIBN in toluene gave methyl (methyl 5,7,8,9-tetra-O-acetyl-4-acylamino-3,4-dideoxy-beta-D-glycero-D-galacto-nonulopyranosid)onate (23, 24, and 25), whereas hydrolysis with HOAc and subsequent debromination with Bu(3)SnH/AIBN in toluene of 32 and 33 gave methyl 5,7,8,9-tetra-O-acetyl-4-acylamino-3,4-dideoxy-beta-D-glycero-D-talo-2-nonulopyranosonate (35 and 36) in the final step of the synthesis. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00302-3