(4R,5R)-4-Allyl-2,2-dimethyl-5-<(phenylsulfonyl)amino>-1,3-dioxane | 150989-66-5

• 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: (4R,5R)-4-Allyl-2,2-dimethyl-5-<(phenylsulfonyl)amino>-1,3-dioxane
• 英文别名: (4R,5R)-5-[(phenylsulfonyl)amino]-4-allyl-2,2-dimethyl-1,3-dioxane；(4R,5R)-4-Allyl-2,2-dimethyl-5-[(phenylsulfonyl)amino]-1,3-dioxane；N-[(4R,5R)-2,2-dimethyl-4-prop-2-enyl-1,3-dioxan-5-yl]benzenesulfonamide
• CAS: 150989-66-5
• 化学式: C₁₅H₂₁NO₄S
• 分子量: 311.402
• InChiKey: BYSJECKSDDDPHJ-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  73
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R,5R)-4-Allyl-2,2-dimethyl-5-<(phenylsulfonyl)amino>-1,3-dioxane 在 ruthenium trichloride 咪唑 、 盐酸 、 4-二甲氨基吡啶 、 sodium periodate 、 硼烷四氢呋喃络合物 、 sodium naphthalenide 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 乙二醇二甲醚 、 phosphate buffer 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 199.5h， 生成 (2R,3R)-6-oxo-3-tert-butyldimethylsilyloxy-2-(tert-butyldimethylsilyloxymethyl)piperidine
  参考文献：
  名称：

  Synthesis of Carbacephems from Serine

  摘要：

  Carbacephems have been synthesized from D-serine by two routes involving construction first of the six-membered ring followed by cyclization to give the bicyclic beta-lactam. In one route, alkylation of a lactim ether was accomplished with Ni(Acac)(2) as a catalyst. The desired R stereochemistry at the carbon corresponding to C-6 of the cephem was obtained by stereospecific hydrogenation of a vinylogous carbamate. The second route involved a stereospecific Michael cyclization to give the same C-6 stereochemistry. Closure of a piperidyl beta-amino acid intermediate common to both routes was accomplished using a modified Mukaiyama reagent found to be superior in our system to the traditional reagent. The resulting carbacephem core was stereospecifically substituted at C-7 with an ethyl or amino functionality. The ethylated intermediate was transformed into a stable enol triflate useful for the further elaboration of biologically important carbacephems.

  DOI：

  10.1021/jo980592s
• 作为产物：
  描述：

  N-(苯基磺酰基)-D-丝氨酸 在 正丁基锂 、 L-Selectride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 72.17h， 生成 (4R,5R)-4-Allyl-2,2-dimethyl-5-<(phenylsulfonyl)amino>-1,3-dioxane
  参考文献：
  名称：

  Synthesis of Carbacephems from Serine

  摘要：

  Carbacephems have been synthesized from D-serine by two routes involving construction first of the six-membered ring followed by cyclization to give the bicyclic beta-lactam. In one route, alkylation of a lactim ether was accomplished with Ni(Acac)(2) as a catalyst. The desired R stereochemistry at the carbon corresponding to C-6 of the cephem was obtained by stereospecific hydrogenation of a vinylogous carbamate. The second route involved a stereospecific Michael cyclization to give the same C-6 stereochemistry. Closure of a piperidyl beta-amino acid intermediate common to both routes was accomplished using a modified Mukaiyama reagent found to be superior in our system to the traditional reagent. The resulting carbacephem core was stereospecifically substituted at C-7 with an ethyl or amino functionality. The ethylated intermediate was transformed into a stable enol triflate useful for the further elaboration of biologically important carbacephems.

  DOI：

  10.1021/jo980592s

文献信息

• Hydroxylated Pyrrolidines. Enantiospecific Synthesis of<i> all-</i><i>cis</i> 2,3,4,5-Substituted Pyrrolidine Derivatives from Serine
  作者：Sharad K. Verma、M. Nieves Atanes、J. Hector Busto、Dung L. Thai、Henry Rapoport

  DOI：10.1021/jo011008+

  日期：2002.2.1

  We report the enantiospecific synthesis of the sterically congested all-cis 2,3,4,5-substituted pyrrolidines 4, 5, and 6, from either D- or L-serine. Hemiaminal intermediate 13 is converted to the fully substituted pyrrolidine 15 by way of a tandem Wittig-Michael reaction. The endo stereochemistry of the C-3 methyl group of compound 15 is set by stereoselective reduction of the double bond in 11, driven

  我们报告了从D-或L-丝氨酸的空间拥挤的全顺式2,3,4,5-取代的吡咯烷4、5和6的对映体特异性合成。通过串联Wittig-Michael反应将半胱氨酸中间体13转化为完全取代的吡咯烷15。化合物15的C-3甲基的内部立体化学是通过11中双键的立体选择性还原来决定的，这是由分子背面的优先氢化决定的。这些完全取代的吡咯烷的全顺式构型已经通过化合物6的X射线分析得到确定。通过萘二甲酸钠的还原成功地从高度取代和官能化的中间体15中除去了苯磺酰基。
• Synthesis of Carbacephems from Serine
  作者：James J. Folmer、Carles Acero、Dung L. Thai、Henry Rapoport

  DOI：10.1021/jo980592s

  日期：1998.11.1

  Carbacephems have been synthesized from D-serine by two routes involving construction first of the six-membered ring followed by cyclization to give the bicyclic beta-lactam. In one route, alkylation of a lactim ether was accomplished with Ni(Acac)(2) as a catalyst. The desired R stereochemistry at the carbon corresponding to C-6 of the cephem was obtained by stereospecific hydrogenation of a vinylogous carbamate. The second route involved a stereospecific Michael cyclization to give the same C-6 stereochemistry. Closure of a piperidyl beta-amino acid intermediate common to both routes was accomplished using a modified Mukaiyama reagent found to be superior in our system to the traditional reagent. The resulting carbacephem core was stereospecifically substituted at C-7 with an ethyl or amino functionality. The ethylated intermediate was transformed into a stable enol triflate useful for the further elaboration of biologically important carbacephems.