Isobutyric acid (2R,3R,4S,5S)-3,5-bis-isobutyryloxy-2-[3-methyl-but-(E)-ylideneamino]-tetrahydro-thiopyran-4-yl ester | 473595-74-3

• 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: Isobutyric acid (2R,3R,4S,5S)-3,5-bis-isobutyryloxy-2-[3-methyl-but-(E)-ylideneamino]-tetrahydro-thiopyran-4-yl ester
• 英文别名: [(3S,4S,5R,6R)-6-(3-methylbutylideneamino)-4,5-bis(2-methylpropanoyloxy)thian-3-yl] 2-methylpropanoate
• CAS: 473595-74-3
• 化学式: C₂₂H₃₇NO₆S
• 分子量: 443.605
• InChiKey: SHFFMOIHELWJLP-FCGDIQPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Isobutyric acid (2R,3R,4S,5S)-3,5-bis-isobutyryloxy-2-[3-methyl-but-(E)-ylideneamino]-tetrahydro-thiopyran-4-yl ester 在 zinc chloride diethyl ether 、 mercury(II) diacetate 、 甲胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 101.0h， 生成 N-((R)-1-tert-Butylcarbamoyl-3-methyl-butyl)-benzamide
  参考文献：
  名称：

  Stereoselective syntheses of α-amino acid and peptide derivatives by the U-4CR of 5-desoxy-5-thio-<small>D</small>-xylopyranosylamine

  摘要：

  Since 1961, the synthesis of alpha-amino acids derivatives by the four-component reaction of isocyanides (U-4CR) as a one-pot reaction has been developed. Only recently it was found that a variety of these cc-amino acids compounds can be formed stereoselectively by the U-4CR using 1-amino-5-deoxy-5-thio-2,3,4-tri-O-isobutanoyl-beta-D-xylopyranose as the amine component. The stereoselectivity inducing auxiliary 5-desoxy-5-thio-D-xylopyranosyl group of the so-formed products can be replaced selectively by hydrogen.

  DOI：

  10.1139/cjc-79-12-1934
• 作为产物：
  描述：

  2,3,4-tri-O-isobutanoyl-5-desoxy-5-thio-D-xylopyranosylazide 在 1,3-丙二硫醇 、 magnesium sulfate 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 Isobutyric acid (2R,3R,4S,5S)-3,5-bis-isobutyryloxy-2-[3-methyl-but-(E)-ylideneamino]-tetrahydro-thiopyran-4-yl ester
  参考文献：
  名称：

  具有1-氨基-5-脱氧-5-硫代-2,3,4- O-异丁酰基-β-d-吡喃木糖的立体选择性U-4CRs-一种有效且可选择性除去的手性助剂

  摘要：

  Ugi四组分反应（U-4CR）为合成α-氨基酸和肽衍生物提供了一条短而直接的途径。用1-氨基-5-脱氧-5-硫代2,3,4- O-异丁酰基-β-d-吡喃吡喃糖作为手性胺组分，可获得优异的化学产率和立体选择性。在U-4CR之后，可以在温和条件下选择性地裂解手性助剂。通过X射线分析确认了其中一种产品的构型。

  DOI：

  10.1016/s0040-4020(02)00484-2

文献信息

• Stereoselective syntheses of α-amino acid and peptide derivatives by the U-4CR of 5-desoxy-5-thio-&lt;small&gt;D&lt;/small&gt;-xylopyranosylamine
  作者：Günther Ross、Ivar Ugi

  DOI：10.1139/cjc-79-12-1934

  日期：——

  Since 1961, the synthesis of alpha-amino acids derivatives by the four-component reaction of isocyanides (U-4CR) as a one-pot reaction has been developed. Only recently it was found that a variety of these cc-amino acids compounds can be formed stereoselectively by the U-4CR using 1-amino-5-deoxy-5-thio-2,3,4-tri-O-isobutanoyl-beta-D-xylopyranose as the amine component. The stereoselectivity inducing auxiliary 5-desoxy-5-thio-D-xylopyranosyl group of the so-formed products can be replaced selectively by hydrogen.
• Stereoselective U-4CRs with 1-amino-5-desoxy-5-thio-2,3,4-O-isobutanoyl-β-d-xylopyranose—an effective and selectively removable chiral auxiliary
  作者：Günther F Ross、Eberhardt Herdtweck、Ivar Ugi

  DOI：10.1016/s0040-4020(02)00484-2

  日期：2002.7

  The Ugi four component reaction (U-4CR) offers a short and direct route for the synthesis of α-amino acid and peptide derivatives. With 1-amino-5-desoxy-5-thio-2,3,4-O-isobutanoyl-β-d-xylopyranose as a chiral amine component excellent chemical yields and stereoselectivities are obtained. After the U-4CR the chiral auxiliary can be cleaved off selectively under mild conditions. The configuration of

  Ugi四组分反应（U-4CR）为合成α-氨基酸和肽衍生物提供了一条短而直接的途径。用1-氨基-5-脱氧-5-硫代2,3,4- O-异丁酰基-β-d-吡喃吡喃糖作为手性胺组分，可获得优异的化学产率和立体选择性。在U-4CR之后，可以在温和条件下选择性地裂解手性助剂。通过X射线分析确认了其中一种产品的构型。