(3S,6R,6aS,7S,9aS)-7-[(2R,3R)-4-(benzyloxy)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-methylbutyl]-3-tert-butyl-6a-hydroxy-6-methyldihydrofuro[3',4':2,3]pyrrolo[1,2-c][1,3]oxazole-5,9(6H)-dione | 1352405-70-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3S,6R,6aS,7S,9aS)-7-[(2R,3R)-4-(benzyloxy)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-methylbutyl]-3-tert-butyl-6a-hydroxy-6-methyldihydrofuro[3',4':2,3]pyrrolo[1,2-c][1,3]oxazole-5,9(6H)-dione
• 英文别名: (1S,4S,7R,8S,9S)-4-tert-butyl-9-[(2R,3R)-3-[tert-butyl(dimethyl)silyl]oxy-2-methyl-4-phenylmethoxybutyl]-8-hydroxy-7-methyl-3,10-dioxa-5-azatricyclo[6.3.0.01,5]undecane-6,11-dione
• CAS: 1352405-70-9
• 化学式: C₃₁H₄₉NO₇Si
• 分子量: 575.818
• InChiKey: UDASNJXRIRIPNF-QJJVQKIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  94.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3S,6R,6aS,7S,9aS)-7-[(2R,3R)-4-(benzyloxy)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-methylbutyl]-3-tert-butyl-6a-hydroxy-6-methyldihydrofuro[3',4':2,3]pyrrolo[1,2-c][1,3]oxazole-5,9(6H)-dione 在 1,3-丙二硫醇 、 盐酸 作用下， 以 2,2,2-三氟乙醇 为溶剂， 反应 0.75h， 以75%的产率得到(3R,3aS,4S,6aS)-4-[(2R,3R)-4-(benzyloxy)-3-hydroxy-2-methylbutyl]-3a-hydroxy-6a-(hydroxymethyl)-3-methyldihydro-1H-furo[3,4-b]pyrrole-2,6(3H,4H)-dione
  参考文献：
  名称：

  Formal synthesis of (+)-neooxazolomycin via a Stille cross-coupling/deconjugation route

  摘要：

  A formal synthesis of neooxazolomycin is described via the preparation of Kende's key intermediate in a longest linear sequence of 23 steps. This work is founded upon the union of three fragments: Moloney's lactam-derived triflate, a vinyl stannane and a Julia-Kocienski sulfone and encompasses three key steps: (i) a Stille cross-coupling to combine the triflate and vinyl stannane, (ii) a base-promoted enone deconjugation to derive the dihydroxylation precursor and (iii) our previously reported Julia-Kocienski methodology to assemble the pentadienyl amine side chain with the sulfone precursor. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.037
• 作为产物：
  描述：

  methyl (R)-2-tert-butyloxazolidine-4-carboxylate 在 吡啶 、 2,6-二甲基吡啶 、 tris-(dibenzylideneacetone)dipalladium(0) 、 四氧化锇 、 三(2-呋喃基)膦 、 potassium tert-butylate 、 水 、 sodium acetate 、 双(三甲基硅烷基)氨基钾 、 N-甲基吗啉氧化物 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 、 对甲苯磺酰肼 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 叔丁醇 为溶剂， 反应 198.0h， 生成 (3S,6R,6aS,7S,9aS)-7-[(2R,3R)-4-(benzyloxy)-3-{[tert-butyl(dimethyl)silyl]oxy}-2-methylbutyl]-3-tert-butyl-6a-hydroxy-6-methyldihydrofuro[3',4':2,3]pyrrolo[1,2-c][1,3]oxazole-5,9(6H)-dione
  参考文献：
  名称：

  Formal synthesis of (+)-neooxazolomycin via a Stille cross-coupling/deconjugation route

  摘要：

  A formal synthesis of neooxazolomycin is described via the preparation of Kende's key intermediate in a longest linear sequence of 23 steps. This work is founded upon the union of three fragments: Moloney's lactam-derived triflate, a vinyl stannane and a Julia-Kocienski sulfone and encompasses three key steps: (i) a Stille cross-coupling to combine the triflate and vinyl stannane, (ii) a base-promoted enone deconjugation to derive the dihydroxylation precursor and (iii) our previously reported Julia-Kocienski methodology to assemble the pentadienyl amine side chain with the sulfone precursor. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.037

文献信息

• Formal synthesis of (+)-neooxazolomycin via a Stille cross-coupling/deconjugation route
  作者：Reyhan Bastin、James W. Dale、Michael G. Edwards、Julien P.N. Papillon、Michael R. Webb、Richard J.K. Taylor

  DOI：10.1016/j.tet.2011.09.037

  日期：2011.12

  A formal synthesis of neooxazolomycin is described via the preparation of Kende's key intermediate in a longest linear sequence of 23 steps. This work is founded upon the union of three fragments: Moloney's lactam-derived triflate, a vinyl stannane and a Julia-Kocienski sulfone and encompasses three key steps: (i) a Stille cross-coupling to combine the triflate and vinyl stannane, (ii) a base-promoted enone deconjugation to derive the dihydroxylation precursor and (iii) our previously reported Julia-Kocienski methodology to assemble the pentadienyl amine side chain with the sulfone precursor. (C) 2011 Elsevier Ltd. All rights reserved.