N-(9-fluorenylmethoxycarbonyl)-O-(2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-α-D-galactopyranosyl)-L-threonine allyl ester | 273944-47-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N-(9-fluorenylmethoxycarbonyl)-O-(2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-α-D-galactopyranosyl)-L-threonine allyl ester
• 英文别名: prop-2-enyl (2S,3R)-3-[[(2S,4aR,6S,7R,8R,8aR)-7-azido-8-(2-chloroacetyl)oxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)butanoate
• CAS: 273944-47-1
• 化学式: C₃₇H₃₇ClN₄O₁₀
• 分子量: 733.175
• InChiKey: PQQKTZMEAZDMPW-XOBMSIMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  52
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  142
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  N-(9-fluorenylmethoxycarbonyl)-O-(2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-α-D-galactopyranosyl)-L-threonine allyl ester 在 硫脲 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以82%的产率得到N^α-fluoren-9-ylmethoxycarbonyl-3-O-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranosyl)-L-threonine allyl ester
  参考文献：
  名称：

  An efficient access to protected disialylated glycohexaosyl threonine present on the leukosialin of activated T-lymphocytes

  摘要：

  The total synthesis of the threonine-linked core 2 class disialylated hexasaccharide in a completely protected form was accomplished for the first time. The L-threonine conjugate, N-(9-fluorenylmethoxycarbonyl)-O-{(5-acetomido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosylanic acid)-(2 --> 3)-(2,6-di-O-benzyl-beta-D-galactopyranosyl)-(1 --> 4)-2-acetamido-2-deoxy-3,6-di-O-benzyl-beta-D-glucopyranosyl-(1 --> 6)-[(5-acctamido-4,7,8,9-tetra-O-benzyl-3, 5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosylonic acid)-(2 --> 3)-2,6-di-O-benzyl-beta-D-galactopyranosyl-(1 --> 3)]-2-acetamido-2-deoxy-alpha-D-galactopyranosyl-(1d --> 4c:1f --> 4e)-dilactone}-L-threonine allyl ester was synthesized via stereocontrolled glycosylations employing readily accessible monosaccharidic blocks; t-butyl-diphenylsilyl-2-azido-2-deoxy-3, 6-di-O-benzyl-beta-D-glucopyranose, N-(9-fluorenylmethoxycarbonyl)-O-(2-azir-butylditnethylsilyl-2-deoxy-alpha-D-galactopyranosyl)-L-threonine allyl ester, 8, 9 and N-(9-fluorenylmethoxycarbonyl)-O-(2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-alpha-D-galactopyranosy;)-L-threonine allyl ester. For the introduction of the amino acid. the azide group was used to temporarily mask the amino group of GalNAc so as to obtain an alpha-glycosidic linkage without participation from the C-2 substituent. The threonine was attached to the sugar unit at the monosaccharide stage to avoid loss of oligosaccharide at a later stage. The Fmoc and allyl ester protected amino acid at the reducing end facilitates efficient glycopeptide synthesis on solid-phase support. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00313-4
• 作为产物：
  描述：

  N-芴甲氧羰基-L-苏氨酸烯丙基酯 、 在 二氯二茂锆 、 4 A molecular sieve 、 silver perchlorate 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到N-(9-fluorenylmethoxycarbonyl)-O-(2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-α-D-galactopyranosyl)-L-threonine allyl ester
  参考文献：
  名称：

  An efficient access to protected disialylated glycohexaosyl threonine present on the leukosialin of activated T-lymphocytes

  摘要：

  The total synthesis of the threonine-linked core 2 class disialylated hexasaccharide in a completely protected form was accomplished for the first time. The L-threonine conjugate, N-(9-fluorenylmethoxycarbonyl)-O-{(5-acetomido-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosylanic acid)-(2 --> 3)-(2,6-di-O-benzyl-beta-D-galactopyranosyl)-(1 --> 4)-2-acetamido-2-deoxy-3,6-di-O-benzyl-beta-D-glucopyranosyl-(1 --> 6)-[(5-acctamido-4,7,8,9-tetra-O-benzyl-3, 5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosylonic acid)-(2 --> 3)-2,6-di-O-benzyl-beta-D-galactopyranosyl-(1 --> 3)]-2-acetamido-2-deoxy-alpha-D-galactopyranosyl-(1d --> 4c:1f --> 4e)-dilactone}-L-threonine allyl ester was synthesized via stereocontrolled glycosylations employing readily accessible monosaccharidic blocks; t-butyl-diphenylsilyl-2-azido-2-deoxy-3, 6-di-O-benzyl-beta-D-glucopyranose, N-(9-fluorenylmethoxycarbonyl)-O-(2-azir-butylditnethylsilyl-2-deoxy-alpha-D-galactopyranosyl)-L-threonine allyl ester, 8, 9 and N-(9-fluorenylmethoxycarbonyl)-O-(2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-alpha-D-galactopyranosy;)-L-threonine allyl ester. For the introduction of the amino acid. the azide group was used to temporarily mask the amino group of GalNAc so as to obtain an alpha-glycosidic linkage without participation from the C-2 substituent. The threonine was attached to the sugar unit at the monosaccharide stage to avoid loss of oligosaccharide at a later stage. The Fmoc and allyl ester protected amino acid at the reducing end facilitates efficient glycopeptide synthesis on solid-phase support. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00313-4