(1S,2S,3R,4R)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-(4,5-dimethyl-furan-2-yl)-2,4-dimethyl-pentan-1-ol | 85828-13-3

• 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: (1S,2S,3R,4R)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-(4,5-dimethyl-furan-2-yl)-2,4-dimethyl-pentan-1-ol
• CAS: 85828-13-3
• 化学式: C₂₆H₄₂O₄Si
• 分子量: 446.703
• InChiKey: LJBSDEMGJLJZNU-CYMHYUIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.81
• 重原子数：
  31.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  51.83
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1S,2S,3R,4R)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-(4,5-dimethyl-furan-2-yl)-2,4-dimethyl-pentan-1-ol 在 三氟化硼乙醚 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.5h， 生成 (1S,3R,4R,5S)-1,4,8-trimethyl-3-[(2R)-1-phenylmethoxypropan-2-yl]-2,9-dioxabicyclo[3.3.1]non-7-en-6-one
  参考文献：
  名称：

  Asymmetric aldol reactions using chiral boron reagents: Application to the synthesis of tirandamycin A

  摘要：

  The bicyclic acetal 1, a key intermediate in previous synthetic studies on tirandamycin A, has been prepared in enantiomerically pure form starting from the (R)-ethylketone 2 and the aldehyde 3. A reagent controlled aldol reaction using (-)-(Ipc)2BOTf selectively gave the 1,2-syn-2,4-syn adduct 4, which was subsequently converted into 1 via the 1,3-anti diol 5.

  DOI：

  10.1016/s0040-4039(00)74320-6
• 作为产物：
  描述：

  4,5-二甲基-2-糠醛 在 2,6-二甲基吡啶 、 pH₇ buffer 、 双氧水 、 potassium carbonate 、 tetramethylammonium triacetoxyborohydride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 溶剂黄146 、 乙腈 为溶剂， 反应 27.67h， 生成 (1S,2S,3R,4R)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-1-(4,5-dimethyl-furan-2-yl)-2,4-dimethyl-pentan-1-ol
  参考文献：
  名称：

  Asymmetric aldol reactions using chiral boron reagents: Application to the synthesis of tirandamycin A

  摘要：

  The bicyclic acetal 1, a key intermediate in previous synthetic studies on tirandamycin A, has been prepared in enantiomerically pure form starting from the (R)-ethylketone 2 and the aldehyde 3. A reagent controlled aldol reaction using (-)-(Ipc)2BOTf selectively gave the 1,2-syn-2,4-syn adduct 4, which was subsequently converted into 1 via the 1,3-anti diol 5.

  DOI：

  10.1016/s0040-4039(00)74320-6

文献信息

• Acid-catalyzed rearrangement of pyran derivatives. An approach to the stereoselective synthesis of 1,3-diol derivatives
  作者：Philip DeShong、David M Simpson、Ming-Teh Lin

  DOI：10.1016/s0040-4039(00)99149-4

  日期：1989.1

  Peracid oxidation and HF-catalyzed treatment of furfuryl alcohol derivatives affords lactone products arising from a highly stereoselective rearrangement process. The lactones serve as precursors of highly functionalized anti-1,3-diol derivatives.

  过酸氧化和糠醛醇衍生物的HF催化处理提供了由高度立体选择性重排过程产生的内酯产物。内酯用作高度官能化的抗-1,3-二醇衍生物的前体。
• Total synthesis of (.+-.)-tirandamycin A
  作者：Philip DeShong、Subban Ramesh、Varadaraj Elango、Joseph J. Perez

  DOI：10.1021/ja00304a031

  日期：1985.9

  Synthese via l'addition du dianion de la diethoxyphosphorylacetyl-3 pyrrolidinedione-2,4 et de l'epoxy-7,8 [formyl-3' methyl-1' butene-2'yl]-3 trimethyl-1,4,8 dioxa-2,9bicyclo [3.3.1] nonanone-6

  这些通过 l'addition du dianion de la diethoxyphosphorylacetyl-3 pyrrolidinedione-2,4 et de l'epoxy-7,8 [formyl-3'methyl-1' butene-2'yl]-3 trimethyl-1,4,8 合成dioxa-2,9bicyclo [3.3.1] nonanone-6
• Total synthesis of tirandamycin. A short, efficient synthesis of the Ireland alcohol
  作者：Philip DeShong、Subban Ramesh、Joseph J. Perez

  DOI：10.1021/jo00160a044

  日期：1983.6