methyl (6S*)-6-(tert-butoxycarbonylamino)-6-hydroxymethyl-4,6-dideoxy-3-C-((1'S*)-1,2-diacetoxyethyl)-α-D-glucopyranoside, 2-acetate | 212958-21-9

• 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 (6S*)-6-(tert-butoxycarbonylamino)-6-hydroxymethyl-4,6-dideoxy-3-C-((1'S*)-1,2-diacetoxyethyl)-α-D-glucopyranoside, 2-acetate
• 英文别名: [(2S)-2-acetyloxy-2-[(2S,3R,4R,6S)-3-acetyloxy-4-hydroxy-6-[(1S)-2-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]-2-methoxyoxan-4-yl]ethyl] acetate
• CAS: 212958-21-9
• 化学式: C₂₁H₃₅NO₁₂
• 分子量: 493.508
• InChiKey: NSOGMYZPKGIYAF-PVTIXZGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  34
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  176
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  methyl (6S*)-6-(tert-butoxycarbonylamino)-6-hydroxymethyl-4,6-dideoxy-3-C-((1'S*)-1,2-diacetoxyethyl)-α-D-glucopyranoside, 2-acetate 在 ruthenium(IV) oxide 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 6.5h， 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：

  (S)-4-((2S,5S)-5-Hydroxy-6-methoxy-4-oxo-tetrahydro-pyran-2-yl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 4-乙基-4-氧代吗啉-4-鎓 、 对甲苯磺酸 吡啶 、 甲醇 、 四氧化锇 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 水 、 丙酮 、 甲苯 、 乙腈 为溶剂， 反应 6.0h， 生成 methyl (6S*)-6-(tert-butoxycarbonylamino)-6-hydroxymethyl-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