methyl (4'S*)-5-(2,2-dimethyl-3-tert-butoxycarbonyl-1,3-oxazolidin-4-yl)-4,6-dideoxy-3-C-((1'S*)-1,2-diacetoxyethyl)-α-D-glucopyranoside, 2-acetate | 212958-15-1

• 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 (4'S*)-5-(2,2-dimethyl-3-tert-butoxycarbonyl-1,3-oxazolidin-4-yl)-4,6-dideoxy-3-C-((1'S*)-1,2-diacetoxyethyl)-α-D-glucopyranoside, 2-acetate
• 英文别名: tert-butyl (4S)-4-[(2S,4R,5R,6S)-5-acetyloxy-4-[(1S)-1,2-diacetyloxyethyl]-4-hydroxy-6-methoxyoxan-2-yl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 212958-15-1
• 化学式: C₂₄H₃₉NO₁₂
• 分子量: 533.573
• InChiKey: NCIOKWYJEYFZAZ-CDZFLWGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  156
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  methyl (4'S*)-5-(2,2-dimethyl-3-tert-butoxycarbonyl-1,3-oxazolidin-4-yl)-4,6-dideoxy-3-C-((1'S*)-1,2-diacetoxyethyl)-α-D-glucopyranoside, 2-acetate 在 ruthenium(IV) oxide 、 对甲苯磺酸 甲醇 、 sodium periodate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 8.5h， 生成 methyl (6R*)-6-[[((1'R,2'S) or (1'S,2'R)-2-acetylaminocyclopentyl)-carbonyl]amino]-4,6-dideoxy-3-C-((1'S*)-1,2-diacetoxyethyl)-α-D-xylo-heptopyranuronate, 1-methyl-2-acetate
  参考文献：
  名称：

  Stereocontrolled and enantioselective synthesis of the branched 6-amino-4,6-deoxyheptopyranuronic acid component of amipurimycin

  摘要：

  A stereocontrolled and enantioselective synthesis of the branched 6-amino-4,6-deoxyheptopyranuronic acid component of amipurimycin is reported. Key stages in the synthesis include the stereodivergent assembly of rile dihydropyrones 12 and 14 from serinal derivatives (S)-10 and (R)-10, elaboration of the tetrahydropyran ring to give 26 and 31, and finally, introduction of the cis-2-aminocyclopentanecarboxylic acid moiety to produce the diastereomeric peptides 28/29 and 32/33. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00585-7
• 作为产物：
  描述：

  methyl (4'S*)-5-(2,2-dimethyl-3-tert-butoxycarbonyl-1,3-oxazolidin-4-yl)-3(E)-(2-hydroxy-ethan-1-ylidene)-3,4,6-trideoxy-α-D-glucopyranoside 在 4-乙基-4-氧代吗啉-4-鎓 吡啶 、 四氧化锇 作用下， 以 水 、 丙酮 为溶剂， 反应 3.0h， 生成 methyl (4'S*)-5-(2,2-dimethyl-3-tert-butoxycarbonyl-1,3-oxazolidin-4-yl)-4,6-dideoxy-3-C-((1'S*)-1,2-diacetoxyethyl)-α-D-glucopyranoside, 2-acetate
  参考文献：
  名称：

  Stereocontrolled and enantioselective synthesis of the branched 6-amino-4,6-deoxyheptopyranuronic acid component of amipurimycin

  摘要：

  A stereocontrolled and enantioselective synthesis of the branched 6-amino-4,6-deoxyheptopyranuronic acid component of amipurimycin is reported. Key stages in the synthesis include the stereodivergent assembly of rile dihydropyrones 12 and 14 from serinal derivatives (S)-10 and (R)-10, elaboration of the tetrahydropyran ring to give 26 and 31, and finally, introduction of the cis-2-aminocyclopentanecarboxylic acid moiety to produce the diastereomeric peptides 28/29 and 32/33. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00585-7