2-benzamido-2-deoxy-1-O-t-butyldiphenylsilyl-4,6-O-ethylidene-3-O-methylsulfonyl-D-glucitol | 220869-68-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-benzamido-2-deoxy-1-O-t-butyldiphenylsilyl-4,6-O-ethylidene-3-O-methylsulfonyl-D-glucitol
• 英文别名: [(1R,2S)-2-benzamido-3-[tert-butyl(diphenyl)silyl]oxy-1-[(2R,4R,5R)-5-hydroxy-2-methyl-1,3-dioxan-4-yl]propyl] methanesulfonate
• CAS: 220869-68-1
• 化学式: C₃₂H₄₁NO₈SSi
• 分子量: 627.831
• InChiKey: DFQASIZWJLEQGG-NNQHHHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-benzamido-2-deoxy-1-O-t-butyldiphenylsilyl-4,6-O-ethylidene-3-O-methylsulfonyl-D-glucitol 在 吡啶 、 盐酸 、 sodium periodate 、 4 A molecular sieve 、 四丁基氟化铵 、 silver trifluoromethanesulfonate 、 四氯化钛 、 苯硫酚 、 三乙胺 、 N,N-二异丙基乙胺 、 n-tetradecylmagnesium chloride 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 51.0h， 生成 (2S,3S,4R,2'R)-1-O-(2''-acetamido-3'',4'',6''-tri-O-acetyl-2''-deoxy-β-D-glucopyranosyl)-3-O-benzoyl-2-(2'-acetoxyhexadecanoyl)aminooctadecane-1,3,4-triol
  参考文献：
  名称：

  Stereocontrolled synthesis of novel phytosphingosine-type glucosaminocerebrosides

  摘要：

  D-ribo-Phytosphingosine 1 was conveniently synthesized from N-benzoyl-D-glucosamine 3 by an improved route in which regioselective O-methanesulfonation and diastereoselective Grignard addition are involved as key steps. Using a synthetic intermediate of 1, novel D-ribo-phytosphingosinetype glycolipids 2a and 2b, unnatural homologues of antifungal cerebrosides Halicylindrosides, were efficiently synthesized in a stereocontrolled manner. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01104-1
• 作为产物：
  描述：

  甲基磺酰氯 、 叔丁基二苯基氯硅烷 、 2-Benzamido-2-deoxy-4,6-O-ethylidene-D-glucitol 在 吡啶 作用下， 生成 [(2R,4S,5R)-4-[(1R,2S)-2-benzamido-3-[tert-butyl(diphenyl)silyl]oxy-1-methylsulfonyloxypropyl]-2-methyl-1,3-dioxan-5-yl] methanesulfonate 、 2-benzamido-2-deoxy-1-O-t-butyldiphenylsilyl-4,6-O-ethylidene-3-O-methylsulfonyl-D-glucitol
  参考文献：
  名称：

  Stereocontrolled synthesis of novel phytosphingosine-type glucosaminocerebrosides

  摘要：

  D-ribo-Phytosphingosine 1 was conveniently synthesized from N-benzoyl-D-glucosamine 3 by an improved route in which regioselective O-methanesulfonation and diastereoselective Grignard addition are involved as key steps. Using a synthetic intermediate of 1, novel D-ribo-phytosphingosinetype glycolipids 2a and 2b, unnatural homologues of antifungal cerebrosides Halicylindrosides, were efficiently synthesized in a stereocontrolled manner. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01104-1

文献信息

• Stereocontrolled synthesis of novel phytosphingosine-type glucosaminocerebrosides
  作者：Teiichi Murakami、Kazuhiro Taguchi

  DOI：10.1016/s0040-4020(98)01104-1

  日期：1999.1

  D-ribo-Phytosphingosine 1 was conveniently synthesized from N-benzoyl-D-glucosamine 3 by an improved route in which regioselective O-methanesulfonation and diastereoselective Grignard addition are involved as key steps. Using a synthetic intermediate of 1, novel D-ribo-phytosphingosinetype glycolipids 2a and 2b, unnatural homologues of antifungal cerebrosides Halicylindrosides, were efficiently synthesized in a stereocontrolled manner. (C) 1999 Elsevier Science Ltd. All rights reserved.