methyl (2S)-2-acetamido-3-[4-{4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl}phenyl]propanoate | 493009-57-7

• 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 (2S)-2-acetamido-3-[4-{4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl}phenyl]propanoate
• 英文别名: methyl (2S)-2-acetamido-3-[4-[(2R,3S,6S)-3-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3,6-dihydro-2H-pyran-6-yl]phenyl]propanoate
• CAS: 493009-57-7
• 化学式: C₃₀H₅₁NO₆Si₂
• 分子量: 577.909
• InChiKey: QPXRIYWJUROOEY-YIPNQBBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.32
• 重原子数：
  39
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-acetamido-3-[4-{4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl}phenyl]propanoate 在 4-甲基-3-吗啉酮 、 四氧化锇 作用下， 以 吡啶 、 水 、 丙酮 为溶剂， 生成 methyl (2S)-2-acetamido-3-[4-{4,6-di-O-(tert-butyldimethylsilyl)-2,3-di-O-acetyl-α-D-mannopyranosyl}phenyl]propanoate
  参考文献：
  名称：

  Stereoselective synthesis of C-glycosyl analogues of phenylalanine

  摘要：

  Condensation of]-[4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-alpha-D-erythro-hex-2-enopyranosyl]-4-bromobenzene (2) with methyl 2-acetamidoacrylate in the presence of Pd(OAc)(2), P(C6H4-O-CH3)(3), and AgNO3, afforded the unsaturated C-glycosyl enamido ester 3d in 80% yield. Reduction of compound 3d in the presence of [Rh(COD)(R,R)-(Et-DuPHOS)]OTf gave the corresponding unsaturated C-glycosyl (R)-phenylalanine derivative, when the [Rh(COD)(S,S)-(Et-DuPHOS)]OTf catalyst gave the C-glycosyl (S)-phenylalanine derivative, in 67 and 79% yield, respectively. Bis-hydroxylation of compound 4, followed by acetylation afforded the C-mannopyranosyl phenylalanine derivative 5 in overall 30% yield. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00831-1
• 作为产物：
  描述：

  1-[4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl]-4-bromobenzene 在 palladium diacetate 、 (-)-1,2-bis-((2R,5R)-2,5-diethylphospholano)benzene(cyclooctadiene) rhodium(I) trifluoromethanesulfonate 、 氢气 、 三乙胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 20.0~100.0 ℃ 、1000.0 kPa 条件下， 反应 36.0h， 生成 methyl (2S)-2-acetamido-3-[4-{4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl}phenyl]propanoate
  参考文献：
  名称：

  Stereoselective synthesis of C-glycosyl analogues of phenylalanine

  摘要：

  Condensation of]-[4,6-di-O-(tert-butyldimethylsilyl)-2,3-dideoxy-alpha-D-erythro-hex-2-enopyranosyl]-4-bromobenzene (2) with methyl 2-acetamidoacrylate in the presence of Pd(OAc)(2), P(C6H4-O-CH3)(3), and AgNO3, afforded the unsaturated C-glycosyl enamido ester 3d in 80% yield. Reduction of compound 3d in the presence of [Rh(COD)(R,R)-(Et-DuPHOS)]OTf gave the corresponding unsaturated C-glycosyl (R)-phenylalanine derivative, when the [Rh(COD)(S,S)-(Et-DuPHOS)]OTf catalyst gave the C-glycosyl (S)-phenylalanine derivative, in 67 and 79% yield, respectively. Bis-hydroxylation of compound 4, followed by acetylation afforded the C-mannopyranosyl phenylalanine derivative 5 in overall 30% yield. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00831-1