Carbonic acid (2S,3R,4R,5S,6R)-2-benzyloxy-5-hydroxy-6-hydroxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester 2,2,2-trichloro-ethyl ester | 114827-03-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Carbonic acid (2S,3R,4R,5S,6R)-2-benzyloxy-5-hydroxy-6-hydroxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester 2,2,2-trichloro-ethyl ester
• 英文别名: [(2R,3S,4R,5R,6S)-3-hydroxy-2-(hydroxymethyl)-6-phenylmethoxy-5-(2,2,2-trichloroethoxycarbonylamino)oxan-4-yl] 2,2,2-trichloroethyl carbonate
• CAS: 114827-03-1
• 化学式: C₁₉H₂₁Cl₆NO₉
• 分子量: 620.095
• InChiKey: GZGZEGUMWVGNKD-RYPNDVFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  133
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  benzyl [fluoro 3-deoxy-4,5-7,8-di-O-isopropylidene-α-D-manno-octulopyranosid]onate 、 Carbonic acid (2S,3R,4R,5S,6R)-2-benzyloxy-5-hydroxy-6-hydroxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-4-yl ester 2,2,2-trichloro-ethyl ester 生成 benzyl (3aR,4R,6R,7aR)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-[[(2R,3S,4R,5R,6S)-3-hydroxy-6-phenylmethoxy-5-(2,2,2-trichloroethoxycarbonylamino)-4-(2,2,2-trichloroethoxycarbonyloxy)oxan-2-yl]methoxy]-2,2-dimethyl-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carboxylate
  参考文献：
  名称：

  IMOTO, MASAHIRO;KUSUNOSE, NAOTO;MATSUURA, YOSHIKI;KUSUMOTO, SHOICHI;SHIBA+, TETRAHEDRON LETT., 28,(1987) N 50, 6277-6280

  摘要：

  DOI：

文献信息

• Preparation of novel pyranosyl fluorides of 3-deoxy-D- -2-octulosonic acid (KDO) feasible for synthesis of KDO α-glycosides
  作者：Masahiro Imoto、Naoto Kusunose、Yoshiki Matsuura、Shoichi Kusumoto、Tetsuo Shiba

  DOI：10.1016/s0040-4039(01)91351-6

  日期：——

  α-Ketopyranosyl fluorides, 2 and 3, of 4,5:7,8-di-O-isopropylidene KDO methyl and benzyl esters were prepared and shown to act as effective glycosyl donors. X-Ray structure analysis of 2 and 1H NMR study established the boat (B3,6) conformation of the di-O-isopropylidene derivatives of KDO and enabled the assignment of their anomeric configurations.

  制备了4,5：7,8-二-O-异亚丙基KDO甲基和苄基酯的α-酮吡喃糖基氟化物2和3，并被证明可作为有效的糖基供体。2和1 H NMR研究的X射线结构分析确定了KDO的二O-异亚丙基衍生物的舟状（B 3,6）构象，并能够指定其端基异构体构型。