tert-butyl (4R)-4-[(1S)-1-hydroxy-3-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]propyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate | 287962-76-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl (4R)-4-[(1S)-1-hydroxy-3-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]propyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 287962-76-9
• 化学式: C₄₇H₅₉NO₉
• 分子量: 781.987
• InChiKey: HTBVHRLUELMXNW-ICDGEIPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  57
• 可旋转键数：
  19
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  tert-butyl (4R)-4-[(1S)-1-hydroxy-3-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]propyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 在 chromium(VI) oxide 、 4-二甲氨基吡啶 、 硫酸 、 N,N'-硫羰基二咪唑 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 9.0h， 生成 6,10-anhydro-7,8,9,11-tetra-O-benzyl-2,3,4,5-tetradeoxy-2-(tert-butoxycarbonylamino)-D-erythro-L-galacto-undeconic acid
  参考文献：
  名称：

  General, stereoselective synthesis of ethylene isosteres of α- and β-glycosylasparagines

  摘要：

  The coupling of alpha- or beta-D-linked lithium C-glycosyl acetylides with N-Boc D-serinal acetonide followed by the reduction of the triple bond, deoxygenation, and oxidative cleavage of the oxazolidine ring afforded alpha- and beta-anomer pairs of C-glycosyl alpha-aminopentanoic acids (gluco, manno, galacto, and 2-acetamido-galacto). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00403-2
• 作为产物：
  描述：

  3,7-脱水-1,2-二脱氧-4,5,6,8-四-O-(苯基甲基)-D-甘油型-D-古洛-辛-1-炔糖醇 在 正丁基锂 、 sodium acetate 、 对甲苯磺酰肼 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 水 为溶剂， 反应 5.0h， 生成 tert-butyl (4R)-4-[(1S)-1-hydroxy-3-[(2S,3S,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]propyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  General, stereoselective synthesis of ethylene isosteres of α- and β-glycosylasparagines

  摘要：

  The coupling of alpha- or beta-D-linked lithium C-glycosyl acetylides with N-Boc D-serinal acetonide followed by the reduction of the triple bond, deoxygenation, and oxidative cleavage of the oxazolidine ring afforded alpha- and beta-anomer pairs of C-glycosyl alpha-aminopentanoic acids (gluco, manno, galacto, and 2-acetamido-galacto). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00403-2

文献信息

• General, stereoselective synthesis of ethylene isosteres of α- and β-glycosylasparagines
  作者：Alessandro Dondoni、Giandomenico Mariotti、Alberto Marra

  DOI：10.1016/s0040-4039(00)00403-2

  日期：2000.4

  The coupling of alpha- or beta-D-linked lithium C-glycosyl acetylides with N-Boc D-serinal acetonide followed by the reduction of the triple bond, deoxygenation, and oxidative cleavage of the oxazolidine ring afforded alpha- and beta-anomer pairs of C-glycosyl alpha-aminopentanoic acids (gluco, manno, galacto, and 2-acetamido-galacto). (C) 2000 Elsevier Science Ltd. All rights reserved.