(2R,3R)-3,4-O-cyclohexylidene-1-phenylbutane-2,3,4-triol | 136465-93-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R)-3,4-O-cyclohexylidene-1-phenylbutane-2,3,4-triol
• 英文别名: alpha(R)-benzyl-1,4-dioxaspiro-[4,5]decane-2(R)-methanol；(1R)-1-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]-2-phenylethanol
• CAS: 136465-93-5
• 化学式: C₁₆H₂₂O₃
• 分子量: 262.349
• InChiKey: ZCKSHHBJRJTDNI-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3,4-O-cyclohexylidene-1-phenylbutane-2,3,4-triol 、 对甲苯磺酰氯 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 反应 6.0h， 以91.1%的产率得到(2R,3R)-3,4-O-cyclohexylidene-2-O-p-toluenesulfonyl-1-phenyl-butane-2,3,4-triol
  参考文献：
  名称：

  A simple and inexpensive procedure for low valent copper mediated benzylation of aldehydes in wet medium: synthesis of protease inhibitor synthon

  摘要：

  An operationally simple, inexpensive and efficient procedure for benzylation of aldehydes in wet medium has been developed that was mediated with low valent copper, prepared in situ through spontaneous reduction of CuCl2-2H(2)O with magnesium in situ. Notably, copper mediated benzylation of 3h took place with good syn selectivity that was opposite to that for the corresponding Grignard addition. Finally, homobenzyl alcohol 5a was elegantly transformed into a known protease inhibitor synthon I.

  DOI：

  10.3998/ark.5550190.0011.912
• 作为产物：
  描述：

  beta(R)-benzyloxy-alpha(RS)-phenyl-1,4-dioxaspiro[4,5]decane-2(R)-ethanol 在 钯 crude product 、 silica gel 、 二氯甲烷 作用下， 以 溶剂黄146 为溶剂， 反应 48.0h， 以There were obtained 60 mg of α(R)-benzyl-1,4-dioxaspiro-[4,5]decane-2(R)-methanol in the form of a colourless oil的产率得到(2R,3R)-3,4-O-cyclohexylidene-1-phenylbutane-2,3,4-triol
  参考文献：
  名称：

  Oxirane intermediates for novel alcohols

  摘要：

  本发明涉及一种新型醇，其化学式为##STR1##其中R.sup.a为偶氮基或邻苯二甲酰亚胺基，R.sup.4为烷基、环烷基、环烷基烷基、芳基或芳基烷基，R.sup.7和R.sup.8共同为三亚甲基或四亚甲基基团，该基团可以被羟基、烷氧羰基氨基或酰胺基取代，或其中一个--CH.sub.2--基团被--NH--、--N(烷氧羰基)--、--N(酰基)--或--S--取代，或者带有融合的环烷基、芳香基或杂芳基环，R.sup.9为烷氧羰基、单烷基氨基甲酰基、单芳基氨基甲酰基、单芳基甲酰基或式中R.sup.10和R.sup.11各自为烷基的基团。同时，本发明还涉及一种制备这些醇的方法。这些醇可用作中间体，例如在制备具有抗病毒活性的氨基酸衍生物时。

  公开号：

  US05508430A1

文献信息

• Alcohols
  申请人：Hoffmann-La Roche Inc.

  公开号：US05516913A1

  公开（公告）日：1996-05-14

  Novel alcohols of the formula ##STR1## wherein R.sup.a is azido or phthalimido, R.sup.4 is alkyl, cycloalkyl, cycloalkylalkyl, aryl or aralkyl, R.sup.7 and R.sup.8 together are a trimethylene or tetramethylene group which is optionally substituted by hydroxy, alkoxycarbonylamino or acylamino or in which one --CH.sub.2 -- group is replaced by --NH--, --N(alkoxycarbonyl)--, --N(acyl)-- or --S-- or which carries a fused cycloalkane, aromatic or heteroaromatic ring, and R.sup.9 is alkoxycarbonyl, monoalkylcarbamoyl, monoaralkylcarbamoyl, monoarylcarbamoyl or a group of the formula ##STR2## in which R.sup.10 and R.sup.11 each is alkyl, are described along with a process for their manufacture. These alcohols are useful as intermediates, for example in the manufacture of amino acid derivatives having antiviral activity.

  化学式为##STR1##的新型醇，其中R.sup.a为偶氮基或邻苯二甲酰亚基，R.sup.4为烷基、环烷基、环烷基烷基、芳基或芳基烷基，R.sup.7和R.sup.8共同为三亚甲基或四亚甲基基团，该基团可选地被羟基、烷氧羰基氨基或酰胺基取代，或其中一个--CH.sub.2--基团被--NH--、--N(烷氧羰基)--、--N(酰基)--或--S--所取代，或者带有融合的环烷基、芳香族或杂芳族环，R.sup.9为烷氧羰基、单烷基氨基甲酰基、单芳基氨基甲酰基、单芳基甲酰基或式子##STR2##中R.sup.10和R.sup.11各自为烷基。同时，还描述了一种制造这些醇的方法。这些醇可用作中间体，例如在制造具有抗病毒活性的氨基酸衍生物时。
• A simple and inexpensive procedure for low valent copper mediated benzylation of aldehydes in wet medium: synthesis of protease inhibitor synthon
  作者：Angshuman Chattopadhyay、Akhil Dubey、Dibakar Goswami

  DOI：10.3998/ark.5550190.0011.912

  日期：——

  An operationally simple, inexpensive and efficient procedure for benzylation of aldehydes in wet medium has been developed that was mediated with low valent copper, prepared in situ through spontaneous reduction of CuCl2-2H(2)O with magnesium in situ. Notably, copper mediated benzylation of 3h took place with good syn selectivity that was opposite to that for the corresponding Grignard addition. Finally, homobenzyl alcohol 5a was elegantly transformed into a known protease inhibitor synthon I.
• Oxirane intermediates for novel alcohols
  申请人：Hoffmann-La Roche Inc.

  公开号：US05508430A1

  公开（公告）日：1996-04-16

  Novel alcohols of the formula ##STR1## wherein R.sup.a is azido or phthalimido, R.sup.4 is alkyl, cycloalkyl, cycloalkylalkyl, aryl or aralkyl, R.sup.7 and R.sup.8 together are a trimethylene or tetramethylene group which is optionally substituted by hydroxy, alkoxycarbonylamino or acylamino or in which one --CH.sub.2 -- group is replaced by --NH--, --N(alkoxycarbonyl)--, --N(acyl)-- or --S-- or which carries a fused cycloalkane, aromatic or heteroaromatic ring, and R.sup.9 is alkoxycarbonyl, monoalkylcarbamoyl, monoaralkylcarbamoyl, monoarylcarbamoyl or a group of the formula ##STR2## in which R.sup.10 and R.sup.11 each is alkyl, are described along with a process for their manufacture. These alcohols are useful as intermediates, for example in the manufacture of amino acid derivatives having antiviral activity.

  本发明涉及一种新型醇，其化学式为##STR1##其中R.sup.a为偶氮基或邻苯二甲酰亚胺基，R.sup.4为烷基、环烷基、环烷基烷基、芳基或芳基烷基，R.sup.7和R.sup.8共同为三亚甲基或四亚甲基基团，该基团可以被羟基、烷氧羰基氨基或酰胺基取代，或其中一个--CH.sub.2--基团被--NH--、--N(烷氧羰基)--、--N(酰基)--或--S--取代，或者带有融合的环烷基、芳香基或杂芳基环，R.sup.9为烷氧羰基、单烷基氨基甲酰基、单芳基氨基甲酰基、单芳基甲酰基或式中R.sup.10和R.sup.11各自为烷基的基团。同时，本发明还涉及一种制备这些醇的方法。这些醇可用作中间体，例如在制备具有抗病毒活性的氨基酸衍生物时。