tert-butyldiphenylsilyl-2,6-di-O-benzyl-β-D-galactopyranoside | 273944-46-0

• 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: tert-butyldiphenylsilyl-2,6-di-O-benzyl-β-D-galactopyranoside
• 英文别名: Bn(-2)[Bn(-6)]Gal(b)-O-TBDPS；(2R,3R,4S,5R,6S)-6-[tert-butyl(diphenyl)silyl]oxy-5-phenylmethoxy-2-(phenylmethoxymethyl)oxane-3,4-diol
• CAS: 273944-46-0
• 化学式: C₃₆H₄₂O₆Si
• 分子量: 598.811
• InChiKey: CJZBWXVYVYGVLB-NVCPMKERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.81
• 重原子数：
  43
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl (2R,3S,4R,5S,6R)-5-acetamido-2-methylsulfanyl-4-phenylmethoxy-3-phenylsulfanyl-6-[(1S,2R)-1,2,3-tris(phenylmethoxy)propyl]oxane-2-carboxylate 、 tert-butyldiphenylsilyl-2,6-di-O-benzyl-β-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 3 A molecular sieve 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以77%的产率得到benzyl (2R,3S,4R,5S,6R)-5-acetamido-2-[(2S,3R,4S,5S,6R)-2-[tert-butyl(diphenyl)silyl]oxy-5-hydroxy-3-phenylmethoxy-6-(phenylmethoxymethyl)oxan-4-yl]oxy-4-phenylmethoxy-3-phenylsulfanyl-6-[(1S,2R)-1,2,3-tris(phenylmethoxy)propyl]oxane-2-carboxylate
  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：

  叔丁基二苯基氯硅烷 在 咪唑 、 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 24.0h， 生成 tert-butyldiphenylsilyl-2,6-di-O-benzyl-β-D-galactopyranoside
  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

文献信息

• An efficient access to protected disialylated glycohexaosyl threonine present on the leukosialin of activated T-lymphocytes
  作者：Latika Singh、Yuko Nakahara、Yukishige Ito、Yoshiaki Nakahara

  DOI：10.1016/s0008-6215(99)00313-4

  日期：2000.4

  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.