(4S,6R)-4-tert-butyldimethylsilyloxy-6-hydroxymethyl-2-cyclohexenone | 338460-84-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,6R)-4-tert-butyldimethylsilyloxy-6-hydroxymethyl-2-cyclohexenone
• 英文别名: (4S,6R)-4-[tert-butyl(dimethyl)silyl]oxy-6-(hydroxymethyl)cyclohex-2-en-1-one
• CAS: 338460-84-7
• 化学式: C₁₃H₂₄O₃Si
• 分子量: 256.417
• InChiKey: MIBFIVUHRPQNDJ-GHMZBOCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.51
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S,6R)-4-tert-butyldimethylsilyloxy-6-hydroxymethyl-2-cyclohexenone 在 potassium osmate(VI) 、 四丁基氟化铵 、 氢气 、 palladium(II) hydroxide 、 四丁基碘化铵 、 三乙酰氧基硼氢化钠 、 sodium hydride 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 水 、 溶剂黄146 、 异丙醇 、 丙酮 为溶剂， 反应 84.5h， 生成 5a-carba-α-D-mannopyranose
  参考文献：
  名称：

  A chemoenzymatic synthesis of 5a-carba-α-d-mannose-6-phosphate

  摘要：

  An efficient chemical synthesis of 5a-carba-alpha-D-mannose and its enzymatic elaboration to 5a-carba-alpha-D-mannose-6-phosphate, using yeast hexokinase, is described. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.04.011
• 作为产物：
  描述：

  (1S,2R,5S)-2,5-Dihydroxy-cyclohex-3-ene-1,2-dicarboxylic acid dimethyl ester 在 咪唑 、 sodium periodate 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.33h， 生成 (4S,6R)-4-tert-butyldimethylsilyloxy-6-hydroxymethyl-2-cyclohexenone
  参考文献：
  名称：

  Asymmetric synthesis of (−)- and (+)-eutipoxide B using a base-catalyzed Diels–Alder reaction

  摘要：

  The asymmetric synthesis of eutipoxide B, a metabolite of the phytopathogenic fungus Eutypa lata, is described. Quick and efficient synthesis of each enantiomer was achieved through base-catalyzed asymmetric Diels-Alder reactions with 3-hydroxy-2-pyrone and chiral acrylates. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00032-1

文献信息

• Synthesis of (+)-epiepoformin using the base-catalyzed Diels–Alder reaction of 3-hydroxy-2-pyrone
  作者：Hideki Shimizu、Hiroaki Okamura、Naomi Yamashita、Tetsuo Iwagawa、Munehiro Nakatani

  DOI：10.1016/s0040-4039(01)01871-8

  日期：2001.12

  Asymmetric total synthesis of (+)-epiepoformin was achieved in short steps using the base-catalyzed asymmetric Diels–Alder (DA) reaction of 3-hydroxy-2-pyrone with chiral acrylate. Since the synthesis produced Ogasawara's intermediate, it is also presented as a formal synthesis of (−)-theobroxide.

  使用碱催化的3-羟基-2-吡喃酮与手性丙烯酸酯的碱催化不对称Diels-Alder（DA）反应可在短时间内完成（+）-表二甲双胍的不对称全合成。由于该合成产生了Ogasawara的中间体，因此它也以（-）-可可氧化物的形式合成形式存在。
• Asymmetric synthesis of (−)- and (+)-eutipoxide B using a base-catalyzed Diels–Alder reaction
  作者：Hideki Shimizu、Hiroaki Okamura、Tetsuo Iwagawa、Munehiro Nakatani

  DOI：10.1016/s0040-4020(01)00032-1

  日期：2001.3

  The asymmetric synthesis of eutipoxide B, a metabolite of the phytopathogenic fungus Eutypa lata, is described. Quick and efficient synthesis of each enantiomer was achieved through base-catalyzed asymmetric Diels-Alder reactions with 3-hydroxy-2-pyrone and chiral acrylates. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Total synthesis of (+)-epiepoformin and (−)-phyllostine
  作者：Hiroaki Okamura、Hideki Shimizu、Naomi Yamashita、Tetsuo Iwagawa、Munehiro Nakatani

  DOI：10.1016/j.tet.2003.10.065

  日期：2003.12

  An efficient asymmetric total synthesis of naturally occurring cyclohexeneoxides, (+)-epiepoformin and (-)-phyllostine has been achieved using the chiral building block available from the base-catalyzed Diels-Alder reaction of 3-hydroxy-2-pyrone. Since (-)-theobroxide was derived from the same precursor of (+)-epiepoformin, the formal total synthesis of (-)-theobroxide has also been achieved. (C) 2003 Elsevier Ltd. All rights reserved.
• A chemoenzymatic synthesis of 5a-carba-α-d-mannose-6-phosphate
  作者：Paula M. Williams、Gary N. Sheldrake、Simon J.F. Macdonald、Chris J. Hamilton

  DOI：10.1016/j.carres.2011.04.011

  日期：2011.7

  An efficient chemical synthesis of 5a-carba-alpha-D-mannose and its enzymatic elaboration to 5a-carba-alpha-D-mannose-6-phosphate, using yeast hexokinase, is described. (C) 2011 Elsevier Ltd. All rights reserved.