(2R,3S,4R,5R,6R,7S,8S,9R,10R)-6,7-Bis(benzyloxy)-2,3-bis<(tert-butyldimethylsilyl)oxy>-8,9:10,11-bis-O-(1-methylethylidene)-2,3,5-trihydroxyundecanoic acid γ-lactone | 130860-96-7

• 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: (2R,3S,4R,5R,6R,7S,8S,9R,10R)-6,7-Bis(benzyloxy)-2,3-bis<(tert-butyldimethylsilyl)oxy>-8,9:10,11-bis-O-(1-methylethylidene)-2,3,5-trihydroxyundecanoic acid γ-lactone
• 英文别名: 8,9:10,11-bis-O-(1-methylethylidene)-6,7-bis-O-(phenylmethyl)-D-glycero-D-galacto-D-galacto-undeconic acid γ-lactone；(3R,4R,5R)-5-[(1R,2S,3R)-3-[(4R,5R)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]-1-hydroxy-2,3-bis(phenylmethoxy)propyl]-3,4-dihydroxyoxolan-2-one
• CAS: 130860-96-7
• 化学式: C₃₁H₄₀O₁₁
• 分子量: 588.652
• InChiKey: XSWXNCXIZWOIQN-WYGCSZBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  142
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,5R,6R,7S,8S,9R,10R)-6,7-Bis(benzyloxy)-2,3-bis<(tert-butyldimethylsilyl)oxy>-8,9:10,11-bis-O-(1-methylethylidene)-2,3,5-trihydroxyundecanoic acid γ-lactone 在 二异丁基氢化铝 、 Rochelle's salt 作用下， 生成 (2R,3R,4S,5R,6S)-6-[(1R,2R)-2-[(4R,5R)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]-1,2-bis(phenylmethoxy)ethyl]oxane-2,3,4,5-tetrol
  参考文献：
  名称：

  Ikemoto, Norihiro; Schreiber, Stuart L., Journal of the American Chemical Society, 1992, vol. 114, # 7, p. 2524 - 2536

  摘要：

  DOI：
• 作为产物：
  描述：

  (2E)-ethyl 2,3,10,11-tetradeoxy-4,5:8,9-bis-O-(1-methylethylidene)-6,7-bis-O-(phenylmethyl)-D-threo-L-galacto-undeca-2,10-dienonate 在 四氧化锇 、 dihydroquinine 4-chlorobenzoate 、 硫酸 、 N-甲基吗啉氧化物 、 三氟乙酸 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 112.0h， 生成 (2R,3S,4R,5R,6R,7S,8S,9R,10R)-6,7-Bis(benzyloxy)-2,3-bis<(tert-butyldimethylsilyl)oxy>-8,9:10,11-bis-O-(1-methylethylidene)-2,3,5-trihydroxyundecanoic acid γ-lactone
  参考文献：
  名称：

  Ikemoto, Norihiro; Schreiber, Stuart L., Journal of the American Chemical Society, 1992, vol. 114, # 7, p. 2524 - 2536

  摘要：

  DOI：

文献信息

• Stereoselective Synthesis of Higher Sugars by Homologation of Carbohydrate-Derived Enals with Nonracemic .gamma.-(Silyloxy) Allylic Stannanes and Substrate-Directed Hydroxylation
  作者：James A. Marshall、Serge Beaudoin

  DOI：10.1021/jo00101a020

  日期：1994.11

  A strategy is described for the chain extension of carbohydrate derivatives utilizing sequential Horner-Emmons condensation and then reduction-oxidation to prepare the enal homologue VII, which is converted to the corresponding dienyl bis-OTBS derivative IX upon condensation with a gamma-(silyloxy) allylic stannane VI and subsequent silylation. Dihydroxylation of dienes M with OsO4-NMO leads to syn,anti,syn,anti,syn. hexol derivatives X with excellent diastereoselectivity. These hexols undergo selective oxidative cleavage with H5IO6 to yield gamma-lactols XI. The methodology has been used to prepare the octonic lactone 15 from (S,S)-dimethyl tartrate and the undeconic lactone 32 from D-mannitol.
• Ikemoto, Norihiro; Schreiber, Stuart L., Journal of the American Chemical Society, 1990, vol. 112, # 26, p. 9657 - 9659
  作者：Ikemoto, Norihiro、Schreiber, Stuart L.

  DOI：——

  日期：——
• Ikemoto, Norihiro; Schreiber, Stuart L., Journal of the American Chemical Society, 1992, vol. 114, # 7, p. 2524 - 2536
  作者：Ikemoto, Norihiro、Schreiber, Stuart L.

  DOI：——

  日期：——