β-(3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)-N-tert-butoxycarbonyl-N,O-isopropylidene-D-alaninol | 230974-63-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-(3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)-N-tert-butoxycarbonyl-N,O-isopropylidene-D-alaninol
• 英文别名: tert-butyl (4R)-4-[[(2S,4R,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]methyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 230974-63-7
• 化学式: C₃₈H₄₉NO₇
• 分子量: 631.81
• InChiKey: VKDKEIVSLVJQSE-UODCSFEZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  46
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  75.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  β-(3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)-N-tert-butoxycarbonyl-N,O-isopropylidene-D-alaninol 在 chromium(VI) oxide 、 硫酸 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 反应 5.5h， 生成 β-(3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)-N-tert-butoxycarbonyl-D-alanine
  参考文献：
  名称：

  Diastereoselective synthesis of β-(3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)-N-tert-butoxycarbonyl-D-alanine

  摘要：

  Key steps in the synthesis of beta-(3,4,6-tri-O-benzyl-2-deoxy-beta-D-galactopyranosyl)-N-tert-butoxycarbonyl-D-alanine are the Wittig reaction of 2-deoxy-galactopyranosylphosphonium salt 2 and Garner aldehyde, as well as the subsequent diastereoselective hydrogenation of the olefinated sugar 3a,b. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00306-3
• 作为产物：
  描述：

  (E/Z)-4,8-anhydro-6,7,9-tri-O-benzyl-2,3,5-trideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-L-glycero-D-lyxo-non-3-enitol 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以100%的产率得到β-(3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)-N-tert-butoxycarbonyl-N,O-isopropylidene-D-alaninol
  参考文献：
  名称：

  Diastereoselective synthesis of β-(3,4,6-tri-O-benzyl-2-deoxy-β-D-galactopyranosyl)-N-tert-butoxycarbonyl-D-alanine

  摘要：

  Key steps in the synthesis of beta-(3,4,6-tri-O-benzyl-2-deoxy-beta-D-galactopyranosyl)-N-tert-butoxycarbonyl-D-alanine are the Wittig reaction of 2-deoxy-galactopyranosylphosphonium salt 2 and Garner aldehyde, as well as the subsequent diastereoselective hydrogenation of the olefinated sugar 3a,b. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00306-3