methyl 7-amino-7-deoxy-1,2:3,4-di-O-isopropylidene-D-erythro-α-D-galacto-octopyranuronate | 147600-21-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 7-amino-7-deoxy-1,2:3,4-di-O-isopropylidene-D-erythro-α-D-galacto-octopyranuronate
• 英文别名: methyl (2S,3R)-2-amino-3-hydroxy-3-[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]propanoate
• CAS: 147600-21-3
• 化学式: C₁₅H₂₅NO₈
• 分子量: 347.365
• InChiKey: IBKCWILOZVMSPI-FJIPNFSISA-N

物化性质

• 沸点：
  479.7±40.0 °C(predicted)
• 密度：
  1.237±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 7-amino-7-deoxy-1,2:3,4-di-O-isopropylidene-D-erythro-α-D-galacto-octopyranuronate 、 ethyl acetimidate hydrochloride 以 二氯甲烷 为溶剂， 反应 6.0h， 以72%的产率得到methyl 7-amino-7-deoxy-1,2:3,4-di-O-isopropylidene-6,7-O,N-ethylidene-D-erythro-α-D-galacto-octopyranuronate
  参考文献：
  名称：

  Silica gel-catalysed addition of methyl nitroacetate to 1,2: 3,4--O--galacto- and 2,3-O-. Crystal structure of methyl 7--O--threo-α--galacto-

  摘要：

  The addition of methyl nitroacetate to 1,2: 3,4-di-O-isopropylidene-alpha-D-galacto-hexodialdo-1,5-pyranose (5) and to 2,3-O-isopropylidene-D-glyceraldehyde (6) in the presence of silica gel led stereoselectively to the formation of only (from 5) or mainly (from 6) two of the four possible nitroaldols in high yield. The catalytic action of silica gel was required in the reaction of 6, but not in that of 5. Isolation of a crystalline, reduced and N-acetylated derivative from the mixture of nitroaldols (7 + 8) obtained from 5 allowed for the determination of its crystal structure, showing that it has the 6R, 7R absolute configuration (one of the two possible 6,7-threo configurations) by X-ray diffraction methods. Therefore, the same 6R configuration was also assigned to the nitroaldols 7 and 8, which on the basis of the easy alpha-epimerisation of the alpha-nitro esters should differ only in the configuration at C-7. A pair of amino alcohols obtained from the same mixture of nitroaldols were separately transformed into a 4,5-cis- and a 4,5-trans-oxazoline, the configurations of which were correlated with the C-6,7 relative configuration of the respective amino alcohols and also the respective nitroaldol. The Felkin model explained the high stereoselectivity observed. The configurations of the two predominant nitroaldols obtained from 6 were tentatively assigned by applying the Felkin model.

  DOI：

  10.1016/0008-6215(95)00027-q
• 作为产物：
  描述：

  1,2：3,4-二-O-异亚丙基-α-D-半乳糖-己二醛-1,5-吡喃糖 在 柠檬酸 、 叔丁醇 作用下， 以 四氢呋喃 为溶剂， 反应 101.5h， 生成 methyl 7-amino-7-deoxy-1,2:3,4-di-O-isopropylidene-D-erythro-α-D-galacto-octopyranuronate
  参考文献：
  名称：

  Diastereoselective Synthesis of Glycosyl-β-hydroxy-α-amino Esters

  摘要：

  We report here the first synthesis of glycosyl-beta-hydroxy-alpha-amino esters by the aldol condensation of a glycine enolate on the aldehyde function of a ribose (1a) or a galactose (1b).

  DOI：

  10.1080/00397919308009763

文献信息

• Diastereoselective Synthesis of Glycosyl-β-hydroxy-α-amino Esters
  作者：M. El Hadrami、J.-P. Lavergne、Ph. Viallefont、A. Chiaroni、C. Riche、A. Hasnaoui

  DOI：10.1080/00397919308009763

  日期：1993.1

  We report here the first synthesis of glycosyl-beta-hydroxy-alpha-amino esters by the aldol condensation of a glycine enolate on the aldehyde function of a ribose (1a) or a galactose (1b).
• Silica gel-catalysed addition of methyl nitroacetate to 1,2: 3,4--O--galacto- and 2,3-O-. Crystal structure of methyl 7--O--threo-α--galacto-
  作者：Pastora Borrachero、María Jesús Diánez、María Dolores Estrada、Manuel Gómez-Guillén、Antonio Gómez-Sánchez、Amparo López-Castro、Simeón Pérez-Garrido

  DOI：10.1016/0008-6215(95)00027-q

  日期：1995.7

  The addition of methyl nitroacetate to 1,2: 3,4-di-O-isopropylidene-alpha-D-galacto-hexodialdo-1,5-pyranose (5) and to 2,3-O-isopropylidene-D-glyceraldehyde (6) in the presence of silica gel led stereoselectively to the formation of only (from 5) or mainly (from 6) two of the four possible nitroaldols in high yield. The catalytic action of silica gel was required in the reaction of 6, but not in that of 5. Isolation of a crystalline, reduced and N-acetylated derivative from the mixture of nitroaldols (7 + 8) obtained from 5 allowed for the determination of its crystal structure, showing that it has the 6R, 7R absolute configuration (one of the two possible 6,7-threo configurations) by X-ray diffraction methods. Therefore, the same 6R configuration was also assigned to the nitroaldols 7 and 8, which on the basis of the easy alpha-epimerisation of the alpha-nitro esters should differ only in the configuration at C-7. A pair of amino alcohols obtained from the same mixture of nitroaldols were separately transformed into a 4,5-cis- and a 4,5-trans-oxazoline, the configurations of which were correlated with the C-6,7 relative configuration of the respective amino alcohols and also the respective nitroaldol. The Felkin model explained the high stereoselectivity observed. The configurations of the two predominant nitroaldols obtained from 6 were tentatively assigned by applying the Felkin model.