(R)-3-[(3aR,5R,6S,6aR)-6-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-3-hydroxy-propionic acid methyl ester | 676139-83-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-3-[(3aR,5R,6S,6aR)-6-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-3-hydroxy-propionic acid methyl ester
• 英文别名: methyl (3R)-3-[(3aR,5R,6S,6aR)-6-[tert-butyl(dimethyl)silyl]oxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-3-hydroxypropanoate
• CAS: 676139-83-6
• 化学式: C₁₇H₃₂O₇Si
• 分子量: 376.522
• InChiKey: NSZNQQSZRQILCW-TVKJYDDYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.18
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (R)-3-[(3aR,5R,6S,6aR)-6-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-3-hydroxy-propionic acid methyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 methyl 6-deoxy-1,2-O-isopropylidene-α-D-gluco-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：

  methyl 3-O-tert-butyldimethylsilyl-6-deoxy-1,2-O-isopropylidene-5-oxo-α-D-xylo-heptofuranuronate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 (R)-3-[(3aR,5R,6S,6aR)-6-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-3-hydroxy-propionic acid methyl ester 、 methyl 3-O-tert-butyldimethylsilyl-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

文献信息

• 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.