dimethyl (4-acetamido-3,7-anhydro-5,6,8-tri-O-benzyl-1,2,4-trideoxy-D-glycero-D-ido-octitol-1-yl)phosphonate | 652993-92-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dimethyl (4-acetamido-3,7-anhydro-5,6,8-tri-O-benzyl-1,2,4-trideoxy-D-glycero-D-ido-octitol-1-yl)phosphonate
• CAS: 652993-92-5
• 化学式: C₃₃H₄₂NO₈P
• 分子量: 611.672
• InChiKey: OVAUGBQGRFGLNW-IZDBAANZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.52
• 重原子数：
  43.0
• 可旋转键数：
  16.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  101.55
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  dimethyl (4-acetamido-3,7-anhydro-5,6,8-tri-O-benzyl-1,2,4-trideoxy-D-glycero-D-ido-octitol-1-yl)phosphonate 在 碘代三甲硅烷 作用下， 以 四氯化碳 为溶剂， 反应 1.0h， 以100%的产率得到(4-acetamido-3,7-anhydro-5,6,8-tri-O-benzyl-1,2,4-trideoxy-D-glycero-D-ido-octitol-1-yl)phosphonic acid
  参考文献：
  名称：

  Synthesis of C‐Glycosyl Phosphate and Phosphonate, Analogues of N‐Acetyl‐α‐d‐Glucosamine 1‐Phosphate

  摘要：

  Synthesis of alpha-C-ethylene phosphate and phosphonate as well as alpha-C-methylene phosphate analogues of N-acetyl-alpha-D-glucosamine I-phosphate is reported starting from the common perbenzylated 2-acetamido-2-deoxy-alpha-C-allyl glucoside. Anomerisation of the corresponding amino alpha-C-glucosyl aldehyde to the beta-aldehyde was observed. Thus, both amino alpha- and beta-C-glucosyl methanol were obtained after reduction.

  DOI：

  10.1081/car-120026465
• 作为产物：
  描述：

  (2'-acetylamino-3',4',5'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)ethanal 在 sodium tetrahydroborate 、 四溴化碳 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 17.0h， 生成 dimethyl (4-acetamido-3,7-anhydro-5,6,8-tri-O-benzyl-1,2,4-trideoxy-D-glycero-D-ido-octitol-1-yl)phosphonate
  参考文献：
  名称：

  Synthesis of C‐Glycosyl Phosphate and Phosphonate, Analogues of N‐Acetyl‐α‐d‐Glucosamine 1‐Phosphate

  摘要：

  Synthesis of alpha-C-ethylene phosphate and phosphonate as well as alpha-C-methylene phosphate analogues of N-acetyl-alpha-D-glucosamine I-phosphate is reported starting from the common perbenzylated 2-acetamido-2-deoxy-alpha-C-allyl glucoside. Anomerisation of the corresponding amino alpha-C-glucosyl aldehyde to the beta-aldehyde was observed. Thus, both amino alpha- and beta-C-glucosyl methanol were obtained after reduction.

  DOI：

  10.1081/car-120026465