(5R)-5-amino-5-cyano-5-deoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-hexofuranose | 1197004-02-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (5R)-5-amino-5-cyano-5-deoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-hexofuranose
• 英文别名: 5-amino-5-cyano-5-deoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose
• CAS: 1197004-02-6
• 化学式: C₁₇H₂₂N₂O₅
• 分子量: 334.372
• InChiKey: SFMXNPWTMYBBOT-OWVAZHOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.66
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  106.96
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  ammonium carbonate 、 (5R)-5-amino-5-cyano-5-deoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-hexofuranose 以 乙醇 、 水 为溶剂， 反应 8.0h， 以77%的产率得到(4R)-4-carbamoyl-4-[(4R)-3-O-benzyl-1,2-O-isopropylidene-β-L-threofuranos-4-C-yl]-oxazolidin-2-one
  参考文献：
  名称：

  Synthesis and X-ray structure of a C5–C4-linked glucofuranose–oxazolidin-2-one

  摘要：

  The formation of (4R)-4-carbamoyl-4-[(4R)-3-O-benzyl-1,2-O-isopropylidene-beta-L-threofuranos-4-C-yl]-oxazolidin-2-one instead of expected imidazolidin-2,4-dione (hydantoin) derivative from 5-amino-5-cyano-5-deoxy-3-O-benzyl-1,2-O-isopropylidene-alpha-D-glucofuranose or 3-O-benzyl-1,2-O-isopropylidene-alpha-D-xylo-hexofuranos-5-ulose under Bucherer-Bergs reaction conditions is reported. Single crystal X-ray diffraction data revealed that T-3(4) is the prefered conformation for the furanose ring, while E-2 and T-2(1) conformations are adopted by the 1,3-dioxolane and 2-oxazolidinone five-membered rings, respectively. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.06.031
• 作为产物：
  描述：

  sodium cyanide 、 3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose 在 氨 、 氯化铵 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以31%的产率得到(5R)-5-amino-5-cyano-5-deoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-xylo-hexofuranose
  参考文献：
  名称：

  Synthesis and X-ray structure of a C5–C4-linked glucofuranose–oxazolidin-2-one

  摘要：

  The formation of (4R)-4-carbamoyl-4-[(4R)-3-O-benzyl-1,2-O-isopropylidene-beta-L-threofuranos-4-C-yl]-oxazolidin-2-one instead of expected imidazolidin-2,4-dione (hydantoin) derivative from 5-amino-5-cyano-5-deoxy-3-O-benzyl-1,2-O-isopropylidene-alpha-D-glucofuranose or 3-O-benzyl-1,2-O-isopropylidene-alpha-D-xylo-hexofuranos-5-ulose under Bucherer-Bergs reaction conditions is reported. Single crystal X-ray diffraction data revealed that T-3(4) is the prefered conformation for the furanose ring, while E-2 and T-2(1) conformations are adopted by the 1,3-dioxolane and 2-oxazolidinone five-membered rings, respectively. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.06.031

文献信息

• Synthesis and X-ray structure of a C5–C4-linked glucofuranose–oxazolidin-2-one
  作者：Bohumil Steiner、Vratislav Langer、Miroslav Koóš

  DOI：10.1016/j.carres.2009.06.031

  日期：2009.10

  The formation of (4R)-4-carbamoyl-4-[(4R)-3-O-benzyl-1,2-O-isopropylidene-beta-L-threofuranos-4-C-yl]-oxazolidin-2-one instead of expected imidazolidin-2,4-dione (hydantoin) derivative from 5-amino-5-cyano-5-deoxy-3-O-benzyl-1,2-O-isopropylidene-alpha-D-glucofuranose or 3-O-benzyl-1,2-O-isopropylidene-alpha-D-xylo-hexofuranos-5-ulose under Bucherer-Bergs reaction conditions is reported. Single crystal X-ray diffraction data revealed that T-3(4) is the prefered conformation for the furanose ring, while E-2 and T-2(1) conformations are adopted by the 1,3-dioxolane and 2-oxazolidinone five-membered rings, respectively. (C) 2009 Elsevier Ltd. All rights reserved.