(E)-(2R,4R,5R,8R)-1-Benzyloxy-9-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-4-methoxy-2,6,8-trimethyl-non-6-en-3-one | 149915-84-4

• 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: (E)-(2R,4R,5R,8R)-1-Benzyloxy-9-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-4-methoxy-2,6,8-trimethyl-non-6-en-3-one
• 英文别名: (E,2R,4R,5R,8R)-9-[tert-butyl(diphenyl)silyl]oxy-5-hydroxy-4-methoxy-2,6,8-trimethyl-1-phenylmethoxynon-6-en-3-one
• CAS: 149915-84-4
• 化学式: C₃₆H₄₈O₅Si
• 分子量: 588.86
• InChiKey: LDFQFTYRQWKFGP-ZJNSJIQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.94
• 重原子数：
  42
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-(2R,4R,5R,8R)-1-Benzyloxy-9-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-4-methoxy-2,6,8-trimethyl-non-6-en-3-one 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 生成 (E)-(2R,3S,4S,5R,8R)-1-Benzyloxy-9-(tert-butyl-diphenyl-silanyloxy)-4-methoxy-2,6,8-trimethyl-non-6-ene-3,5-diol
  参考文献：
  名称：

  High π-face selectivity in anti aldol reactions of E-enol borinates from chiral alkoxymethyl ketones: stereocontrolled synthesis of a C24-C32 polyol subunit of rapamycin

  摘要：

  Using (c-C6H11)2BCl/Et3N, the aldol reactions of the alpha-chiral alkoxymethyl ketones 5 and 6 with achiral aldehydes gives the 1,2-anti-2,4-anti adducts 7 and 8 in 83-95% yield with greater-than-or-equal-to 95% diastereoselectivity. This novel aldol reaction was applied to a concise and highly stereocontrolled synthesis of the C24-C32 subunit 9 of, rapamycin (10).

  DOI：

  10.1021/jo00068a002
• 作为产物：
  描述：

  (2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal 在 氯代二环己基硼烷 、 二异丁基氢化铝 、 三乙胺 作用下， 反应 15.5h， 生成 (E)-(2R,4R,5R,8R)-1-Benzyloxy-9-(tert-butyl-diphenyl-silanyloxy)-5-hydroxy-4-methoxy-2,6,8-trimethyl-non-6-en-3-one
  参考文献：
  名称：

  High π-face selectivity in anti aldol reactions of E-enol borinates from chiral alkoxymethyl ketones: stereocontrolled synthesis of a C24-C32 polyol subunit of rapamycin

  摘要：

  Using (c-C6H11)2BCl/Et3N, the aldol reactions of the alpha-chiral alkoxymethyl ketones 5 and 6 with achiral aldehydes gives the 1,2-anti-2,4-anti adducts 7 and 8 in 83-95% yield with greater-than-or-equal-to 95% diastereoselectivity. This novel aldol reaction was applied to a concise and highly stereocontrolled synthesis of the C24-C32 subunit 9 of, rapamycin (10).

  DOI：

  10.1021/jo00068a002

文献信息

• High π-face selectivity in anti aldol reactions of E-enol borinates from chiral alkoxymethyl ketones: stereocontrolled synthesis of a C24-C32 polyol subunit of rapamycin
  作者：Ian Paterson、Richard D. Tillyer

  DOI：10.1021/jo00068a002

  日期：1993.7

  Using (c-C6H11)2BCl/Et3N, the aldol reactions of the alpha-chiral alkoxymethyl ketones 5 and 6 with achiral aldehydes gives the 1,2-anti-2,4-anti adducts 7 and 8 in 83-95% yield with greater-than-or-equal-to 95% diastereoselectivity. This novel aldol reaction was applied to a concise and highly stereocontrolled synthesis of the C24-C32 subunit 9 of, rapamycin (10).