(2R,3R)-3-azido-1,2-O-isopropylidene-5-hexen-1,2-diol | 155012-73-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R)-3-azido-1,2-O-isopropylidene-5-hexen-1,2-diol
• 英文别名: (1R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-butenylazide；(S)-4-((R)-1-azidobut-3-enyl)-2,2-dimethyl-1,3-dioxolane；(4S)-4-[(1R)-1-azidobut-3-enyl]-2,2-dimethyl-1,3-dioxolane
• CAS: 155012-73-0
• 化学式: C₉H₁₅N₃O₂
• 分子量: 197.237
• InChiKey: KWLBGHJMLLSWAO-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  32.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-azido-1,2-O-isopropylidene-5-hexen-1,2-diol 在 lithium aluminium tetrahydride 、 sodium hydride 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 23.25h， 生成 tert-butyl N-allyl-N-(1R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-butenylcarbamate
  参考文献：
  名称：

  方便的全合成旋光哌啶和吲哚利兹定生物碱（-）-β-conhydrine和（-）-lentiginosine

  摘要：

  朝向哌啶和吲哚里生物碱的stereocontroled总合成涉及尝试导致的合成（ - ） - β-conhydrine 1和（ - ） - lentiginosine 3。1和3的合成是由受保护的d-甘露醇作为手性前体开发的，其中涉及亲核加成和叠氮化物亲核取代，Barbier烯丙基化，闭环易位和Sharpless不对称二羟基化为关键步骤。

  DOI：

  10.1016/j.tet.2010.11.011
• 作为产物：
  描述：

  1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol 在 叠氮化锂 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (2R,3R)-3-azido-1,2-O-isopropylidene-5-hexen-1,2-diol
  参考文献：
  名称：

  Indium-mediated allylation of aldehydes: A convenient route to 2-deoxy and 2,6-dideoxy carbohydrates

  摘要：

  The allylation of protected polyhydroxy aldehydes 1 and 14 has been achieved by indium metal with ultrasound promotion generating the diastereomeric pair of homoallylic polyols 3, 4 and 16, 17 respectively with moderate to good stereoselectivity. Pursuing this allylation strategy with the corresponding deprotected polyhydroxy aldehydes led to the same pair of homoallylic polyols but with a quite different ratio of the diastereomers generated. The polyols were further transformed to 2-deoxy (5 and 6) and 2,6-dideoxy (18 and 19) carbohydrates by ozonolysis.

  DOI：

  10.1016/s0040-4020(01)80790-0

文献信息

• Stereoselective total synthesis of (+)-β-conhydrine from d-mannitol
  作者：Ahmed Kamal、Saidi Reddy Vangala、N.V. Subba Reddy、V. Santhosh Reddy

  DOI：10.1016/j.tetasy.2009.10.017

  日期：2009.11

  An asymmetric synthesis of the piperidine alkaloid (+)-β-conhydrine has been developed starting from (R)-protected glyceraldehyde as the chiral precursor using Barbier allylation, azide nucleophilic substitution, and ring-closing metathesis as the key steps.

  以Barbier烯丙基化，叠氮化物亲核取代和闭环复分解为关键步骤，从（R）-保护的甘油醛作为手性前体开始，开发了哌啶生物碱（+）-β-conhydrine的不对称合成。
• An expedient total synthesis of optically active piperidine and indolizidine alkaloids (−)-β-conhydrine and (−)-lentiginosine
  作者：Ahmed Kamal、Saidi Reddy Vangala

  DOI：10.1016/j.tet.2010.11.011

  日期：2011.2

  Attempts directed toward the stereocontroled total synthesis of piperidine and indolizidine alkaloids resulted in the synthesis of (−)-β-conhydrine 1 and (−)-lentiginosine 3. The synthesis of 1 and 3 were developed from protected d-mannitol as the chiral precursor, which involved nucleophilic addition and azide nucleophilic substitution, Barbier allylation, ring closing metathesis, and Sharpless asymmetric

  朝向哌啶和吲哚里生物碱的stereocontroled总合成涉及尝试导致的合成（ - ） - β-conhydrine 1和（ - ） - lentiginosine 3。1和3的合成是由受保护的d-甘露醇作为手性前体开发的，其中涉及亲核加成和叠氮化物亲核取代，Barbier烯丙基化，闭环易位和Sharpless不对称二羟基化为关键步骤。
• Indium-mediated allylation of aldehydes: A convenient route to 2-deoxy and 2,6-dideoxy carbohydrates
  作者：Wolfgang H. Binder、Reinhard H. Prenner、Walther Schmid

  DOI：10.1016/s0040-4020(01)80790-0

  日期：1994.1

  The allylation of protected polyhydroxy aldehydes 1 and 14 has been achieved by indium metal with ultrasound promotion generating the diastereomeric pair of homoallylic polyols 3, 4 and 16, 17 respectively with moderate to good stereoselectivity. Pursuing this allylation strategy with the corresponding deprotected polyhydroxy aldehydes led to the same pair of homoallylic polyols but with a quite different ratio of the diastereomers generated. The polyols were further transformed to 2-deoxy (5 and 6) and 2,6-dideoxy (18 and 19) carbohydrates by ozonolysis.