(3S,5S)-3-Amino-5-hydroxymethyl-2(3H)-dihydrofuranone hydrochloride | 134790-13-9

• 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: (3S,5S)-3-Amino-5-hydroxymethyl-2(3H)-dihydrofuranone hydrochloride
• 英文别名: [(3S,5S)-5-(hydroxymethyl)-2-oxooxolan-3-yl]azanium;chloride
• CAS: 134790-13-9
• 化学式: C₅H₉NO₃*ClH
• 分子量: 167.592
• InChiKey: JVWZBARLZWMWMK-MMALYQPHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.09
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  74.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,5S)-3-Amino-5-hydroxymethyl-2(3H)-dihydrofuranone hydrochloride 、 氯甲酸苄酯 在 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 生成 (3S,5S)-3-benzyloxycarbonylamino-5-hydroxy-γ-lactone
  参考文献：
  名称：

  Chelation controlled 1,3-dipolar cycloaddition of 5,6-Dihydro-5-phenyl-1,4-oxazin-2-one N-oxide with allyl alcohols: A short-step synthesis of clavalanine intermediate

  摘要：

  (R)-5, 6-Dihydro-5-phenyl-1,4-oxazin-2-one N-oxide {(R)-2} reacts with allyl alcohols 3a-c in the presence of magnesium bromide from the less hindered face via exo-mode to afford corresponding cycloadducts 4a-c with excellent stereoselection. Treatment of (R)-2 with three equivalents of racemic secondary allyl alcohols 3d-g under the same conditions causes partial kinetic resolution to give 4d-g as main products among eight possible stereoisomers. Cycloadduct ent-4a from (S)-2 and 3a was converted directly to g-lactone 6, which is known as the key synthetic intermediate of antibiotic clavalanine. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02476-9
• 作为产物：
  描述：

  2-Amino-2-deoxy-3,4-O-benzylidene-1,5-D-ribonolactone 在 Raney Ni W-2 盐酸 、 Dowex 50Wx₂ 、 氢气 、 sodium hydride 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 为溶剂， -20.0~25.0 ℃ 、2.0 kPa 条件下， 反应 19.75h， 生成 (3S,5S)-3-Amino-5-hydroxymethyl-2(3H)-dihydrofuranone hydrochloride
  参考文献：
  名称：

  由D-核糖内酯立体选择性合成4,5-二羟基-D-赤型-和4,5-二羟基-D-苏型-L-正缬氨酸

  摘要：

  为了制备标题非天然氨基酸，已经在D-核糖内酯衍生物的C-2位立体选择性地引入了氮功能。合成策略在于S N 2型取代反应中构型的反转和便利取代的丁烯内酯的立体定向氢化。的异构体是在抗生素clavalanine的合成中的关键前体。

  DOI：

  10.1016/s0040-4020(01)85821-x

文献信息

• Chelation controlled 1,3-dipolar cycloaddition of 5,6-Dihydro-5-phenyl-1,4-oxazin-2-one N-oxide with allyl alcohols: A short-step synthesis of clavalanine intermediate
  作者：Osamu Tamura、Takahiro Kuroki、Yuta Sakai、Jun-ichi Takizawa、Jun Yoshino、Yasuhiro Morita、Naka Mita、Kentoku Gotanda、Masanori Sakamoto

  DOI：10.1016/s0040-4039(98)02476-9

  日期：1999.1

  (R)-5, 6-Dihydro-5-phenyl-1,4-oxazin-2-one N-oxide (R)-2} reacts with allyl alcohols 3a-c in the presence of magnesium bromide from the less hindered face via exo-mode to afford corresponding cycloadducts 4a-c with excellent stereoselection. Treatment of (R)-2 with three equivalents of racemic secondary allyl alcohols 3d-g under the same conditions causes partial kinetic resolution to give 4d-g as main products among eight possible stereoisomers. Cycloadduct ent-4a from (S)-2 and 3a was converted directly to g-lactone 6, which is known as the key synthetic intermediate of antibiotic clavalanine. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Stereoselective Synthesis of 4,5-Dihydroxy-D-erythro- and 4,5-Dihydroxy-D-threo-L-norvaline from D-Ribonolactone
  作者：Jesús Ariza、Miguel Díaz、Josep Font、Rosa M. Ortuño

  DOI：10.1016/s0040-4020(01)85821-x

  日期：1993.2

  Nitrogen functions have been introduced stereoselectively at the C-2 position in D-ribonolactone derivatives in order to prepare the title unnatural amino acids. The synthetic strategies lie in the inversion of configuration in SN2-type substitution reactions and stereospecific hydrogenation of conveniently substituted butenolides. The -isomer is the key precursor in the synthesis of the antibiotic

  为了制备标题非天然氨基酸，已经在D-核糖内酯衍生物的C-2位立体选择性地引入了氮功能。合成策略在于S N 2型取代反应中构型的反转和便利取代的丁烯内酯的立体定向氢化。的异构体是在抗生素clavalanine的合成中的关键前体。