methyl 3-O-tert-butyldimethylsilyl-6-deoxy-1,2-O-isopropylidene-5-oxo-α-D-xylo-heptofuranuronate | 676139-79-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: methyl 3-O-tert-butyldimethylsilyl-6-deoxy-1,2-O-isopropylidene-5-oxo-α-D-xylo-heptofuranuronate
• 英文别名: methyl 3-[(3aR,5S,6R,6aR)-6-[tert-butyl(dimethyl)silyl]oxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-3-oxopropanoate
• CAS: 676139-79-0
• 化学式: C₁₇H₃₀O₇Si
• 分子量: 374.507
• InChiKey: WUJLRAQSCMZXOB-LXTVHRRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.39
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 3-O-tert-butyldimethylsilyl-6-deoxy-1,2-O-isopropylidene-5-oxo-α-D-xylo-heptofuranuronate 在 sodium tetrahydroborate 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.5h， 生成 methyl 6-deoxy-1,2-O-isopropylidene-β-l-ido-heptofuranuronate
  参考文献：
  名称：

  Asymmetric hydrogenations of glycoside derived β-ketoesters

  摘要：

  The catalytic hydrogenation of beta-ketoesters bearing a sugar moiety at C-3 is reported. Hydrogenations in the presence of chiral ruthenium(II) complexes are highly diastereoselective. The hydrogenation stereoselectivity of the ribose derived beta-ketoester was controlled by the catalyst. The C-5 substituent of the xylose derived beta-ketoester influenced the stereochemical course of the catalytic hydrogenation: the diastereoselectivity was controlled by the substrate if the C-5 substituent is a bulky group. (C) 2003 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2003.11.001
• 作为产物：
  描述：

  3-O-[(t-butyl)dimethylsilyl]-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 在 chromium(VI) oxide 、 sodium periodate 、 硫酸 、 溶剂黄146 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 乙醇 、 水 、 丙酮 为溶剂， 反应 80.0h， 生成 methyl 3-O-tert-butyldimethylsilyl-6-deoxy-1,2-O-isopropylidene-5-oxo-α-D-xylo-heptofuranuronate
  参考文献：
  名称：

  Diastereoselective syntheses of 1-deoxyhomonojirimycin and two new 1,5,6-trideoxy-1,5-iminoheptitols with d-allo- and l-talo-configuration

  摘要：

  The synthesis of 1-deoxyhomonojirimycin 2, as well as two new diastereomers, namely 1,5,6-trideoxy-1,5-imino-D-allo-heptitol 3 and 1,5,6-trideoxy-1,5-imino-L-talo-heptitol 4, is described. Compound 2 was obtained from 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose-while 3 and 4 were obtained from 1, 2:5,6-di-O-isopropylidene-alpha-D-allofuranose. These compounds were transformed in a few steps to the corresponding beta-ketoesters 12 and 18, respectively, which were hydrogenated diastereoselectively in the presence of chiral ruthenium complexes with total control of the C-5 stereogenic centre. The resulting beta-hydroxyesters 13, 19a and 19b are key intermediates for the syntheses of the 1,5,6-trideoxy-1,5-iminoheptitols 2, 3 and 4, respectively. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.07.022

文献信息

• Diastereoselective syntheses of 1-deoxyhomonojirimycin and two new 1,5,6-trideoxy-1,5-iminoheptitols with d-allo- and l-talo-configuration
  作者：Géraldine Le Bouc、Christine Thomassigny、Christine Greck

  DOI：10.1016/j.tetasy.2006.07.022

  日期：2006.8

  The synthesis of 1-deoxyhomonojirimycin 2, as well as two new diastereomers, namely 1,5,6-trideoxy-1,5-imino-D-allo-heptitol 3 and 1,5,6-trideoxy-1,5-imino-L-talo-heptitol 4, is described. Compound 2 was obtained from 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose-while 3 and 4 were obtained from 1, 2:5,6-di-O-isopropylidene-alpha-D-allofuranose. These compounds were transformed in a few steps to the corresponding beta-ketoesters 12 and 18, respectively, which were hydrogenated diastereoselectively in the presence of chiral ruthenium complexes with total control of the C-5 stereogenic centre. The resulting beta-hydroxyesters 13, 19a and 19b are key intermediates for the syntheses of the 1,5,6-trideoxy-1,5-iminoheptitols 2, 3 and 4, respectively. (c) 2006 Elsevier Ltd. All rights reserved.
• Asymmetric hydrogenations of glycoside derived β-ketoesters
  作者：C. Thomassigny、C. Greck

  DOI：10.1016/j.tetasy.2003.11.001

  日期：2004.1

  The catalytic hydrogenation of beta-ketoesters bearing a sugar moiety at C-3 is reported. Hydrogenations in the presence of chiral ruthenium(II) complexes are highly diastereoselective. The hydrogenation stereoselectivity of the ribose derived beta-ketoester was controlled by the catalyst. The C-5 substituent of the xylose derived beta-ketoester influenced the stereochemical course of the catalytic hydrogenation: the diastereoselectivity was controlled by the substrate if the C-5 substituent is a bulky group. (C) 2003 Published by Elsevier Ltd.