phenyl 3,4-dideoxy-2-O-(2,2-dimethylpropionyl)-6-O-(phenylmethyl)-1-thio-3-trifluoroacetamido-β-D-glucopyranoside | 157068-61-6

• 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: phenyl 3,4-dideoxy-2-O-(2,2-dimethylpropionyl)-6-O-(phenylmethyl)-1-thio-3-trifluoroacetamido-β-D-glucopyranoside
• 英文别名: phenyl 6-O-benzyl-3,4-dideoxy-2-O-(2,2-dimethylpropionyl)-1-thio-3-trifluoroacetamido-α-D-glucopyranoside；pivaloyl(-2)[TfaNH(-3d)][Bn(-6)]4-deoxy-D-xylHex(b)-SPh；[(2S,3R,4S,6S)-6-(phenylmethoxymethyl)-2-phenylsulfanyl-4-[(2,2,2-trifluoroacetyl)amino]oxan-3-yl] 2,2-dimethylpropanoate
• CAS: 157068-61-6
• 化学式: C₂₆H₃₀F₃NO₅S
• 分子量: 525.589
• InChiKey: VMWNHEIRDOOXMM-UVUJQTEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  99.2
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  phenyl 3,4-dideoxy-2-O-(2,2-dimethylpropionyl)-6-O-(phenylmethyl)-1-thio-3-trifluoroacetamido-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 3 A molecular sieve 、 水 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.34h， 生成 methyl 3-amino-3-deoxy-4-<3',4'-dideoxy-2'-O-(2,2-dimethylpropionyl)-6'-O-(phenylmethyl)-3'-(trifluoroacetamido)-β-D-glucopyranosyl>-2-O-methyl-6-O-(phenylmethyl)-3-N-<(trichloroacetamido)carbonyl>-β-D-gulopyranoside
  参考文献：
  名称：

  An Ezomycin Model Glycosylation

  摘要：

  A model glycosylation reaction for application to the synthesis of the ezomycin class of antibiotics is described. The ezoaminuroic thioglycoside donor 13, with a reduced and protected C-6 position and trifluoroacetamide at C-3, was prepared from the Cerny epoxide 7 by a nine-step procedure. The model D-pulo-pyranoside acceptor 20, which closely resembles an actual acceptor in the vicinity of the reacting axial hydroxyl, was synthesized from methyl beta-D-galactopyranoside 14. Glycosylation with N-iodosuccinimide/triflic acid as promoter gave the disaccharide 21 in 90% yield.

  DOI：

  10.1021/jo00096a022
• 作为产物：
  描述：

  phenyl 3-azido-3,4-dideoxy-2-O-(2,2-dimethylpropionyl)-6-O-(phenylmethyl)-1-thio-β-D-glucopyranoside 在 水 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 phenyl 3,4-dideoxy-2-O-(2,2-dimethylpropionyl)-6-O-(phenylmethyl)-1-thio-3-trifluoroacetamido-β-D-glucopyranoside
  参考文献：
  名称：

  An Ezomycin Model Glycosylation

  摘要：

  A model glycosylation reaction for application to the synthesis of the ezomycin class of antibiotics is described. The ezoaminuroic thioglycoside donor 13, with a reduced and protected C-6 position and trifluoroacetamide at C-3, was prepared from the Cerny epoxide 7 by a nine-step procedure. The model D-pulo-pyranoside acceptor 20, which closely resembles an actual acceptor in the vicinity of the reacting axial hydroxyl, was synthesized from methyl beta-D-galactopyranoside 14. Glycosylation with N-iodosuccinimide/triflic acid as promoter gave the disaccharide 21 in 90% yield.

  DOI：

  10.1021/jo00096a022

文献信息

• Synthesis of the Ezomycin Nucleoside Disaccharide
  作者：Spencer Knapp、Vijay K. Gore

  DOI：10.1021/ol005696f

  日期：2000.5.1

  [equation--see text] A protected ezomycin octosyl nucleoside was glycosylated at O-6' with a protected ezoaminuroic acid donor to afford, following several functional group modifications, the title compound 1 ( identical with 4-desamino-4-oxoezomycin A(2)).

  [等式-参见文字]将受保护的ezomycin八糖核苷与受保护的ezoaminuroic酸供体在O-6'处糖基化，经过几个官能团修饰后，提供标题化合物1（与4-desamino-4-oxoezomycin A相同（ 2））。
• An Ezomycin Model Glycosylation
  作者：Spencer Knapp、Carlos Jaramillo、Brett Freeman

  DOI：10.1021/jo00096a022

  日期：1994.8

  A model glycosylation reaction for application to the synthesis of the ezomycin class of antibiotics is described. The ezoaminuroic thioglycoside donor 13, with a reduced and protected C-6 position and trifluoroacetamide at C-3, was prepared from the Cerny epoxide 7 by a nine-step procedure. The model D-pulo-pyranoside acceptor 20, which closely resembles an actual acceptor in the vicinity of the reacting axial hydroxyl, was synthesized from methyl beta-D-galactopyranoside 14. Glycosylation with N-iodosuccinimide/triflic acid as promoter gave the disaccharide 21 in 90% yield.