methyl (p-tolyl 5-acetamido-4,7,8-tri-O-tert-butyldimethylsilyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranosid)onate | 819814-52-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (p-tolyl 5-acetamido-4,7,8-tri-O-tert-butyldimethylsilyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranosid)onate
• 英文别名: methyl (2S,4S,5S,6R)-5-acetamido-6-[(1S,2R)-1,2-bis[[tert-butyl(dimethyl)silyl]oxy]-3-hydroxypropyl]-4-[tert-butyl(dimethyl)silyl]oxy-2-(4-methylphenyl)sulfanyloxane-2-carboxylate
• CAS: 819814-52-3
• 化学式: C₃₇H₆₉NO₈SSi₃
• 分子量: 772.279
• InChiKey: PSWRCXQUQDUPRU-NMFDZPRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.41
• 重原子数：
  50
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl (p-tolyl 5-acetamido-4,7,8-tri-O-tert-butyldimethylsilyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranosid)onate 在 三乙胺三氧化硫 、 Dowex 50 (Na⁺) 作用下， 以 N,N-二甲基甲酰胺 、 甲醇 为溶剂， 反应 1.0h， 以87%的产率得到methyl (p-tolyl 5-acetamido-7,8-di-O-tert-butyldimethylsilyl-3,5-dideoxy-9-O-sulfo-2-thio-D-glycero-α-D-galacto-non-2-ulopyranosid)onate sodium salt
  参考文献：
  名称：

  Chemoselective deprotection of acid labile primary hydroxyl protecting groups under CBr4-photoirradiation conditions

  摘要：

  The CBr4-photoirradiation in methanol generates a controlled source of HBr, which can chemoselectively deprotect commonly used hydroxyl-protecting groups in saccharides and nucleosides, such as tert-butyldimethylsilyl, isopropylidene, benzylidene and triphenyl ethers in the presence of other acid-labile functional groups. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.095
• 作为产物：
  描述：

  (2S,4S,5R,6R)-5-Acetylamino-4-hydroxy-2-p-tolylsulfanyl-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 四溴化碳 、 lutidine 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 methyl (p-tolyl 5-acetamido-4,7,8-tri-O-tert-butyldimethylsilyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranosid)onate
  参考文献：
  名称：

  Chemoselective deprotection of acid labile primary hydroxyl protecting groups under CBr4-photoirradiation conditions

  摘要：

  The CBr4-photoirradiation in methanol generates a controlled source of HBr, which can chemoselectively deprotect commonly used hydroxyl-protecting groups in saccharides and nucleosides, such as tert-butyldimethylsilyl, isopropylidene, benzylidene and triphenyl ethers in the presence of other acid-labile functional groups. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.095

文献信息

• <i>N</i>-Trifluoroacetyl Sialyl Phosphite Donors for the Synthesis of α(2 → 9) Oligosialic Acids
  作者：Chang-Ching Lin、Kuo-Ting Huang、Chun-Cheng Lin

  DOI：10.1021/ol0515210

  日期：2005.9.1

  A new method for the synthesis of alpha(2 -> 9) oligosialic acids is developed using phosphite sialyl donors that are protected with a C-5 N-trifluoroacetyl (NHTFA) substituent. Compared with conventional donors, these donors gave a higher degree of alpha-anomeric selectivity during glycosidic bond formation and better yields during iterative sialylation in the synthesis of oligosialic acids.