phenyl 2,3,4-tri-O-benzyl-6-O-(4-methoxyphenyl)methyl-1-thio-β-D-galactopyranoside | 1192142-49-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3,4-tri-O-benzyl-6-O-(4-methoxyphenyl)methyl-1-thio-β-D-galactopyranoside
• 英文别名: phenyl 2,3,4-tri-O-benzyl-6-O-p-methoxybenzyl-1-thio-β-D-galactopyranoside；(2R,3S,4S,5R,6S)-2-[(4-methoxyphenyl)methoxymethyl]-3,4,5-tris(phenylmethoxy)-6-phenylsulfanyloxane
• CAS: 1192142-49-6
• 化学式: C₄₁H₄₂O₆S
• 分子量: 662.847
• InChiKey: MGEMTKPQZPOXRS-RSGFCBGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  48
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  80.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  phenyl 2,3,4-tri-O-benzyl-6-O-(4-methoxyphenyl)methyl-1-thio-β-D-galactopyranoside 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 水 、 丙酮 为溶剂， 反应 0.33h， 生成 2,3,4-tri-O-benzyl-6-O-p-methoxybenzyl-β-D-galactopyranose 、 2,3,4-tri-O-benzyl-6-O-p-methoxybenzyl-α-D-galactopyranose
  参考文献：
  名称：

  Sequential one-pot glycosylation with glycosyl N-trichloroacetylcarbamate and trichloroacetate including dehydrative approach using 1-hydroxy sugars

  摘要：

  An efficient sequential one-pot glycosylation has been developed with glycosyl trichlorocarbamate and trichloroacetate activated by the same Lewis acid and enabled by a change in reaction temperature. The act-selective glycosylation was achieved using glucose, galactose, and mannose substrates after investigation into the reactivities of the two types of glycosyl donors. Sequential one-pot dehydrative glycosylation, including in situ preparation of glycosyl donors followed by generation of two glycosyl bonds, provided three types of trisaccharide. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2011.06.006
• 作为产物：
  描述：

  phenyl 2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranoside 、 4-甲氧基氯苄 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以98%的产率得到phenyl 2,3,4-tri-O-benzyl-6-O-(4-methoxyphenyl)methyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Sequential one-pot glycosylation with glycosyl N-trichloroacetylcarbamate and trichloroacetate including dehydrative approach using 1-hydroxy sugars

  摘要：

  An efficient sequential one-pot glycosylation has been developed with glycosyl trichlorocarbamate and trichloroacetate activated by the same Lewis acid and enabled by a change in reaction temperature. The act-selective glycosylation was achieved using glucose, galactose, and mannose substrates after investigation into the reactivities of the two types of glycosyl donors. Sequential one-pot dehydrative glycosylation, including in situ preparation of glycosyl donors followed by generation of two glycosyl bonds, provided three types of trisaccharide. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2011.06.006

文献信息

• Solid-phase synthesis of O-sulfated glycopeptide by the benzyl-protected glycan strategy
  作者：Keita Kawahira、Hiromasa Tanaka、Akiharu Ueki、Yuko Nakahara、Hironobu Hojo、Yoshiaki Nakahara

  DOI：10.1016/j.tet.2009.07.080

  日期：2009.9

  To expand the repertoire of our benzyl-protection strategy for solid-phase glycopeptide synthesis, an C-sulfated glycopeptide was chosen as the synthetic target. Trisaccharyl serine derivatives (Gal beta 1-4-GlcNAc beta 1-2-Many alpha 1-3-Ser) carrying (4-methoxyphenyl)methyl (MPM) groups at either 3-O or 6-O of the Gal residue were prepared through three stereoselective glycosylations. Cleavage of MPM followed by reaction with Me3N center dot SO3 efficiently afforded 3-O- and 6-O-sulfo-glycoserines, respectively. A preliminary debenzylation Study using the sulfated glycoserines revealed that the sulfate groups persisted under 'low-acidity TfOH' conditions, when using a limited amount of TfOH and extending the reaction period. The 3-O-sulfo-glycoserine was then introduced into an icosapeptide modeled after an alpha-dystroglycan fragment by a combination of automated and manual solid-phase peptide synthesis procedures. The synthesized glycopeptide was successfully debenzylated by the low-acidity TfOH cocktail with slight damage to the sulfate functionality. (C) 2009 Elsevier Ltd. All rights reserved.