tert-butyldiphenylsilyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside | 496052-69-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyldiphenylsilyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• 英文别名: 2-[(2S,3R,4R,5S,6R)-2-[tert-butyl(diphenyl)silyl]oxy-4-phenylmethoxy-6-(phenylmethoxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-3-yl]isoindole-1,3-dione
• CAS: 496052-69-8
• 化学式: C₇₈H₇₉NO₁₂Si
• 分子量: 1250.57
• InChiKey: LYYFFVITFPJOFC-KUDFZRFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.84
• 重原子数：
  92
• 可旋转键数：
  28
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  130
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  tert-butyldiphenylsilyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以91%的产率得到2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-D-glucopyranose
  参考文献：
  名称：

  Synthesis of Core-class 2O-Linked Glycopeptides: a Benzyl-protected Tetrasaccharyl Serine and its Derivative Carrying a Hydrophobic Cholestanyl Group

  摘要：

  一种核心类2的四糖链接丝氨酸以汇聚方式合成。双糖糖基给体3与受体4的偶联反应立体选择性地合成了四糖15，随后将其转化为糖基氟化物20。用20对Fmoc丝氨酸烯丙酯5进行糖基化反应分别以40%和33%的产率得到了α-和β-糖苷。α异构体21被转化为1，这是固相合成糖肽的有用构建模块。另一方面，21进行了N-脱保护，并通过琥珀酰间隔基与疏水的胆固醇醇缩合。同样，该化合物也可通过20与28的偶联反应来合成。功能基团的操控和氢化得到了核心2四糖-胆固醇醇结合物2。

  DOI：

  10.1271/bbb.66.1904
• 作为产物：
  描述：

  tert-butyldiphenylsilyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 sodium methylate 、 四丁基碘化铵 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 tert-butyldiphenylsilyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Core-class 2O-Linked Glycopeptides: a Benzyl-protected Tetrasaccharyl Serine and its Derivative Carrying a Hydrophobic Cholestanyl Group

  摘要：

  一种核心类2的四糖链接丝氨酸以汇聚方式合成。双糖糖基给体3与受体4的偶联反应立体选择性地合成了四糖15，随后将其转化为糖基氟化物20。用20对Fmoc丝氨酸烯丙酯5进行糖基化反应分别以40%和33%的产率得到了α-和β-糖苷。α异构体21被转化为1，这是固相合成糖肽的有用构建模块。另一方面，21进行了N-脱保护，并通过琥珀酰间隔基与疏水的胆固醇醇缩合。同样，该化合物也可通过20与28的偶联反应来合成。功能基团的操控和氢化得到了核心2四糖-胆固醇醇结合物2。

  DOI：

  10.1271/bbb.66.1904

文献信息

• Synthesis of biantennary LacNAc-linked O-glycan (core 4) and glycopeptide thioester by benzyl protection strategy: rapid zinc reduction of GlcNTCA to GlcNAc by microwave irradiation
  作者：Akiharu Ueki、Yuko Nakahara、Hironobu Hojo、Yoshiaki Nakahara

  DOI：10.1016/j.tet.2006.12.088

  日期：2007.3

  A synthetic method for the core 4 O-glycan-linked Ser and Thr was developed. Highly stereoselective 3-O- and 6-O-glycosylation was achieved by using two distinctively protected N-trichloroacetyllactosaminyl fluorides (3 and 12). Microwave-assisted Zn reduction rapidly and efficiently converted N-trichloroacetylglucosamine (GlcNTCA) to N-acetylglucosamine (GlcNAc). In order to demonstrate the usefulness of the protected core 4 O-glycan a segment (Gly(34)-Gly(58)) of emmprin (extracellular matrix metalloproteinase inducer), a cancer metastasis-related glycoprotein, was synthesized by the solid-phase method, utilizing the pentasaccharyl Thr (2) to introduce an O-glycan in place of the native N-glycan at Asn(44). (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis of Core-class 2<i>O</i>-Linked Glycopeptides: a Benzyl-protected Tetrasaccharyl Serine and its Derivative Carrying a Hydrophobic Cholestanyl Group
  作者：Jun WATABE、Latika SINGH、Yuko NAKAHARA、Yukishige ITO、Hironobu HOJO、Yoshiaki NAKAHARA

  DOI：10.1271/bbb.66.1904

  日期：2002.1

  A core-class 2 tetrasaccharide-linked serine was synthesized in a convergent manner. The coupling reaction of disaccharide glycosyl donor 3 and acceptor 4 stereoselectively afforded tetrasaccharide 15, which was converted to glycosyl fluoride 20. Glycosylation of Fmoc serine allyl ester 5 with 20 produced α- and β-glycosides in 40% and 33% yields, respectively. α-Isomer 21 was converted into 1, a useful building block for the solid-phase synthesis of glycopeptides. On the other hand, 21 was N-deprotected and condensed with hydrophobic cholestanol through a succinyl spacer. The same compound was alternatively synthesized by coupling 20 and 28. Functional group manipulation and hydrogenation afforded core 2 tetrasaccharide-cholestanol conjugate 2.

  一种核心类2的四糖链接丝氨酸以汇聚方式合成。双糖糖基给体3与受体4的偶联反应立体选择性地合成了四糖15，随后将其转化为糖基氟化物20。用20对Fmoc丝氨酸烯丙酯5进行糖基化反应分别以40%和33%的产率得到了α-和β-糖苷。α异构体21被转化为1，这是固相合成糖肽的有用构建模块。另一方面，21进行了N-脱保护，并通过琥珀酰间隔基与疏水的胆固醇醇缩合。同样，该化合物也可通过20与28的偶联反应来合成。功能基团的操控和氢化得到了核心2四糖-胆固醇醇结合物2。