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 | 212958-01-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 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
• 英文别名: tert-butyl (4S)-4-[(2S,4E,5R,6S)-5-hydroxy-4-(2-hydroxyethylidene)-6-methoxyoxan-2-yl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 212958-01-5
• 化学式: C₁₈H₃₁NO₇
• 分子量: 373.447
• InChiKey: CYTGHSLWGXVCGR-ZBRNASRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  97.7
• 氢给体数：
  2
• 氢受体数：
  7

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)-3(E)-(2-hydroxy-ethan-1-ylidene)-3,4,6-trideoxy-α-D-glucopyranoside 在 ruthenium(IV) oxide 、 4-乙基-4-氧代吗啉-4-鎓 、 对甲苯磺酸 吡啶 、 甲醇 、 sodium periodate 、 四氧化锇 作用下， 以 水 、 丙酮 为溶剂， 反应 8.0h， 生成 methyl (6R*)-6-(tert-butoxycarbonylamino)-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)-methoxy-carbonylidene-3,4,6-trideoxy-α-D-glucopyranoside 在 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.0h， 以98%的产率得到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
  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

文献信息

• Stereocontrolled and enantioselective synthesis of the branched 6-amino-4,6-deoxyheptopyranuronic acid component of amipurimycin
  作者：Philip Garner、Ji Uk Yoo、Ramakanth Sarabu、Vance O Kennedy、Wiley J Youngs

  DOI：10.1016/s0040-4020(98)00585-7

  日期：1998.8

  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.