benzyl ((4S,4'R,5R)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-ylmethyl)carbamate | 214619-43-9

• 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: benzyl ((4S,4'R,5R)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-ylmethyl)carbamate
• 英文别名: benzyl N-[[(4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]methyl]carbamate
• CAS: 214619-43-9
• 化学式: C₁₉H₂₇NO₆
• 分子量: 365.426
• InChiKey: GCKDBQCLVZTSFI-OAGGEKHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl ((4S,4'R,5R)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-ylmethyl)carbamate 在 水 、 碘 、 二正丁基氧化锡 、 potassium carbonate 、 magnesium 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 2.58h， 生成 [(1R)-1-[(4S,5R)-2,2-dimethyl-5-(phenylmethoxycarbonylaminomethyl)-1,3-dioxolan-4-yl]-2-(4-methoxyphenyl)ethyl] methanesulfonate
  参考文献：
  名称：

  A facile and stereoselective synthesis of the C-2 epimer of (+)-deacetylanisomycin

  摘要：

  A short, simple and efficient synthesis of the C-2 epimer of (+)-deacetylanisomycin starting from D-mannitol, utilizing an epoxide opening with a Grignard reagent and acid catalysed unusual intramolecular 5-endo-tet cyclization as key steps has been reported. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.01.021
• 作为产物：
  描述：

  mannitol triacetonide 在 sodium tetrahydroborate 、 sodium azide 、 palladium 10% on activated carbon 、 氢气 、 sodium carbonate 、 过碘酸 、 三乙胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.08h， 生成 benzyl ((4S,4'R,5R)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-ylmethyl)carbamate
  参考文献：
  名称：

  A facile and stereoselective synthesis of the C-2 epimer of (+)-deacetylanisomycin

  摘要：

  A short, simple and efficient synthesis of the C-2 epimer of (+)-deacetylanisomycin starting from D-mannitol, utilizing an epoxide opening with a Grignard reagent and acid catalysed unusual intramolecular 5-endo-tet cyclization as key steps has been reported. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.01.021

文献信息

• Chirospecific synthesis of 1,4-dideoxy-1,4-imino-D-arabinitol and 1,4-dideoxy-1,4-imino-L-xylitol via one-pot cyclisation
  作者：Jin Hyo Kim、Min Suk Yang、Woo Song Lee、Ki Hun Park

  DOI：10.1039/a803342k

  日期：——

  The multi-protected compounds 4 and 5 were treated with 20% iodine in methanol to give 1,4-dideoxy-1,4-imino-D-arabinitol 1 and 1,4-dideoxy-1,4-imino-L-xylitol 2 directly. Iodine was an efficient catalyst for deprotection of O-isopropylidene, O-(tert-butyldimethylsilyl), N-(9-phenylfluoren-9-yl) and N-benzyloxycarbonyl groups, resulting in intramolecular cyclisation.

  经多重保护的化合物4和5，以20%碘的甲醇溶液处理，直接生成1,4-二去氧-1,4-亚胺基-D-阿拉伯糖醇1和1,4-二去氧-1,4-亚胺基-L-木糖醇2。碘作为高效的催化剂，能够去除O-异丙叉、O-(叔丁基二甲基硅基)、N-(9-苯基芴-9-基)和N-苄氧羰基等保护基团，从而实现分子内环化。
• A facile and stereoselective synthesis of the C-2 epimer of (+)-deacetylanisomycin
  作者：K. Sridhar Reddy、B. Venkateswara Rao

  DOI：10.1016/j.tetasy.2011.01.021

  日期：2011.1

  A short, simple and efficient synthesis of the C-2 epimer of (+)-deacetylanisomycin starting from D-mannitol, utilizing an epoxide opening with a Grignard reagent and acid catalysed unusual intramolecular 5-endo-tet cyclization as key steps has been reported. (C) 2011 Elsevier Ltd. All rights reserved.