(S)-Amino-((2R,3R,4R,5S)-3,4,5-triacetoxy-tetrahydro-furan-2-yl)-acetic acid methyl ester | 127559-14-2

• 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: (S)-Amino-((2R,3R,4R,5S)-3,4,5-triacetoxy-tetrahydro-furan-2-yl)-acetic acid methyl ester
• 英文别名: methyl (2S)-2-amino-2-[(2R,3R,4R,5S)-3,4,5-triacetyloxyoxolan-2-yl]acetate
• CAS: 127559-14-2
• 化学式: C₁₃H₁₉NO₉
• 分子量: 333.295
• InChiKey: OARFDRADIQVMPA-ZZZDWPBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  140
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (S)-Amino-((2R,3R,4R,5S)-3,4,5-triacetoxy-tetrahydro-furan-2-yl)-acetic acid methyl ester 、 氯甲酸苄酯 在 碳酸氢钠 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.75h， 以92.8%的产率得到methyl 5-deoxy-5-[[(phenylmethoxy)carbonyl]amino]-β-D-allohexofuranuronate 1,2,3-triacetate
  参考文献：
  名称：

  A formal synthesis of thymine polyoxin C

  摘要：

  A convergent stereoselective synthesis of thymine polyoxin C 1 has been conducted utilizing the benzylimine of D-glueraldehyde acetonide 7 as a chiral controller and 2-trimethylsilyloxy furan 8 as a four-carbon synthon. In the presence of catalytic BF(3)center dot OEt2, 8 has been found to add to 7 with a moderately high level of stereoselectivity. Intermediate 4-(aminoalkyl)-2-butenolide 6 proved to be an ideal candidate for elaboration to 3. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.03.034
• 作为产物：
  描述：

  methyl 5-N-benzylamino-5-deoxy-β-D-allohexofuranuronate 1,2,3-triacetate 在 palladium on activated charcoal 氢气 、 sodium acetate 作用下， 以 四氢呋喃 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 13.5h， 以75.6%的产率得到(S)-Amino-((2R,3R,4R,5S)-3,4,5-triacetoxy-tetrahydro-furan-2-yl)-acetic acid methyl ester
  参考文献：
  名称：

  A formal synthesis of thymine polyoxin C

  摘要：

  A convergent stereoselective synthesis of thymine polyoxin C 1 has been conducted utilizing the benzylimine of D-glueraldehyde acetonide 7 as a chiral controller and 2-trimethylsilyloxy furan 8 as a four-carbon synthon. In the presence of catalytic BF(3)center dot OEt2, 8 has been found to add to 7 with a moderately high level of stereoselectivity. Intermediate 4-(aminoalkyl)-2-butenolide 6 proved to be an ideal candidate for elaboration to 3. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.03.034

文献信息

• GARNER, PHILIP;PARK, JUNG MIN, TETRAHEDRON LETT., 30,(1989) N8, C. 5065-5068
  作者：GARNER, PHILIP、PARK, JUNG MIN

  DOI：——

  日期：——