(4S,5S)-4-(t-butyldiphenylsilyl)oxymethyl-2-phenyl-4,5-dihydrooxazole-5-carbaldehyde | 220869-71-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (4S,5S)-4-(t-butyldiphenylsilyl)oxymethyl-2-phenyl-4,5-dihydrooxazole-5-carbaldehyde
• 英文别名: (4S,5S)-4-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-phenyl-4,5-dihydro-1,3-oxazole-5-carbaldehyde
• CAS: 220869-71-6
• 化学式: C₂₇H₂₉NO₃Si
• 分子量: 443.618
• InChiKey: SZCLRWWJWACDGN-LOSJGSFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,5S)-4-(t-butyldiphenylsilyl)oxymethyl-2-phenyl-4,5-dihydrooxazole-5-carbaldehyde 在 盐酸 、 4 A molecular sieve 、 四丁基氟化铵 、 silver trifluoromethanesulfonate 、 三乙胺 、 n-tetradecylmagnesium chloride 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 1,2-二氯乙烷 为溶剂， 反应 4.17h， 生成 (2S,3S,4R)-1-O-(2''-acetamido-3'',4'',6''-tri-O-acetyl-2''-deoxy-β-D-glucopyranosyl)-3-O-benzoyl-2-hexadecanoylaminooctadecane-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：

  2-Benzamido-2-deoxy-4,6-O-ethylidene-D-glucitol 在 吡啶 、 sodium periodate 、 四氯化钛 、 苯硫酚 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 56.0h， 生成 (4S,5S)-4-(t-butyldiphenylsilyl)oxymethyl-2-phenyl-4,5-dihydrooxazole-5-carbaldehyde
  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.