(S)-2,2-Dimethyl-4-[(E)-2-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-oxazolidine-3-carboxylic acid tert-butyl ester | 204187-65-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2,2-Dimethyl-4-[(E)-2-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-oxazolidine-3-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (4S)-2,2-dimethyl-4-[(E)-2-[(2S,3S,4R,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]ethenyl]-1,3-oxazolidine-3-carboxylate
• CAS: 204187-65-5
• 化学式: C₄₆H₅₅NO₈
• 分子量: 749.945
• InChiKey: JWRXEJHZMVNHAH-GJFLULJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  55
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  84.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (S)-2,2-Dimethyl-4-[(E)-2-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-oxazolidine-3-carboxylic acid tert-butyl ester 在 sodium acetate 、 对甲苯磺酰肼 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 3.0h， 生成 5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-threo-L-galacto-decitol
  参考文献：
  名称：

  Stereoselective synthesis of the C-linked analogue of β-d-galactopyranosyl-l-serine

  摘要：

  The coupling of the D-serinal derivative 7 with the D-galactopyranosylmethylene phosphorane generated from the phosphonium salt 6 and reduction of the resulting alkene led to the C-glycosylated amino alcohol 9 that in turn was oxidized to the title amino acid in 44% overall yield. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)83019-6
• 作为产物：
  描述：

  (2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)methyl alcohol 在 咪唑 、 正丁基锂 、 4 Angstroem MS 、 碘 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 6.0h， 生成 (S)-2,2-Dimethyl-4-[(E)-2-((2S,3S,4R,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-vinyl]-oxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Stereoselective synthesis of the C-linked analogue of β-d-galactopyranosyl-l-serine

  摘要：

  The coupling of the D-serinal derivative 7 with the D-galactopyranosylmethylene phosphorane generated from the phosphonium salt 6 and reduction of the resulting alkene led to the C-glycosylated amino alcohol 9 that in turn was oxidized to the title amino acid in 44% overall yield. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)83019-6

文献信息

• Stereoselective synthesis of the C-linked analogue of β-d-galactopyranosyl-l-serine
  作者：Alessandro Dondoni、Alberto Marra、Alessandro Massi

  DOI：10.1016/s0040-4020(98)83019-6

  日期：1998.3

  The coupling of the D-serinal derivative 7 with the D-galactopyranosylmethylene phosphorane generated from the phosphonium salt 6 and reduction of the resulting alkene led to the C-glycosylated amino alcohol 9 that in turn was oxidized to the title amino acid in 44% overall yield. (C) 1998 Elsevier Science Ltd. All rights reserved.