Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-diacetylamino-6-methylsulfanyl-tetrahydro-pyran-4-yl ester | 171973-79-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-diacetylamino-6-methylsulfanyl-tetrahydro-pyran-4-yl ester
• 英文别名: [(2R,3R,4R,5R,6S)-3,4-diacetyloxy-5-(diacetylamino)-6-methylsulfanyloxan-2-yl]methyl acetate
• CAS: 171973-79-8
• 化学式: C₁₇H₂₅NO₉S
• 分子量: 419.453
• InChiKey: IUJUAFMRJSAMLU-UUAJXVIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  151
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  benzyl 2'',6''-di-O-benzyl-β-galactopyranosyl-(1''->4')-2',3',6'-tri-O-benzyl-α,β-glucopyranoside 、 Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-diacetylamino-6-methylsulfanyl-tetrahydro-pyran-4-yl ester 在 DMTST 作用下， 以 二氯甲烷 为溶剂， 以51%的产率得到
  参考文献：
  名称：

  N,N-Diacetyl-Glucosamine and -Galactosamine Derivatives as Glycosyl Donors

  摘要：

  N-Acetyl-glucosamine and N-acetyl-galactosamine were converted into the O-acetyl protected 1-methylthio-derivatives 1A,B which were then transformed into N,N-diacetyl derivatives 2A and 2B, respectively. Activation of 2A,B with DMTST afforded good glycosyl donors for the generation of P-linkages: thus, reaction with accepters 3a,b gave oligosaccharides 4Aa and 4Ba in high and 4Ab and 4Bb in good yields. Mono-N-deacetylation could be performed with NaOMe/MeOH in quantitative yield, thus concluding a convenient procedure for the formation of beta-linked GlcNAc and GalNAc glycosides.

  DOI：

  10.1016/00404-0399(50)14068-
• 作为产物：
  描述：

  乙酰氯 、 Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-methylsulfanyl-tetrahydro-pyran-4-yl ester 在 N,N-二异丙基乙胺 作用下， 以91%的产率得到Acetic acid (2R,3R,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-diacetylamino-6-methylsulfanyl-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  N,N-Diacetyl-Glucosamine and -Galactosamine Derivatives as Glycosyl Donors

  摘要：

  N-Acetyl-glucosamine and N-acetyl-galactosamine were converted into the O-acetyl protected 1-methylthio-derivatives 1A,B which were then transformed into N,N-diacetyl derivatives 2A and 2B, respectively. Activation of 2A,B with DMTST afforded good glycosyl donors for the generation of P-linkages: thus, reaction with accepters 3a,b gave oligosaccharides 4Aa and 4Ba in high and 4Ab and 4Bb in good yields. Mono-N-deacetylation could be performed with NaOMe/MeOH in quantitative yield, thus concluding a convenient procedure for the formation of beta-linked GlcNAc and GalNAc glycosides.

  DOI：

  10.1016/00404-0399(50)14068-

文献信息

• METHODS OF SYNTHESIZING GM2
  申请人：LUDWIG INSTITUTE FOR CANCER RESEARCH

  公开号：EP0821691B1

  公开（公告）日：2003-08-06
• US5756695A
  申请人：——

  公开号：US5756695A

  公开（公告）日：1998-05-26