Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-[4-(6-acryloylamino-hexanoylamino)-benzyloxy]-tetrahydro-pyran-4-yl ester | 158979-48-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-[4-(6-acryloylamino-hexanoylamino)-benzyloxy]-tetrahydro-pyran-4-yl ester
• CAS: 158979-48-7
• 化学式: C₃₀H₄₁N₃O₁₁
• 分子量: 619.669
• InChiKey: KLGAMNUISUGTQS-WVUACWIUSA-N

物化性质

• 沸点：
  846.2±65.0 °C(predicted)
• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.66
• 重原子数：
  44.0
• 可旋转键数：
  16.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  184.66
• 氢给体数：
  3.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-[4-(6-acryloylamino-hexanoylamino)-benzyloxy]-tetrahydro-pyran-4-yl ester 在 palladium on activated charcoal 四甲基乙二胺 、 galactosyl transferase 、 HEPES buffer 、 氢气 、 sodium methylate 、 丙烯酰胺 、 6-氨基-9-[3,4-二羟基-5-[(羟基-磺基氧基-磷酰)氧基甲基]四氢呋喃-2-基]-嘌呤 、 α-lactalbumin 作用下， 以 甲醇 为溶剂， 反应 87.0h， 生成 N-acetyl-D-lactosamine
  参考文献：
  名称：

  High performance polymer supports for enzyme-assisted synthesis of glycoconjugates

  摘要：

  Efficient and practical methodology for the construction of carbohydrates, including oligosaccharide derivatives and sphingoglycolipids, was established on the basis of a water-soluble polymer supports having unique linkers that can be cleaved by specific conditions. Novel glycomonomers for the construction of polymer supports were synthesized and copolymerized with acrylamide to give three types of water-soluble glycopolymers having primer sugars through the specific linkers containing (i) p-substituted benzyl group, (ii) L-phenylalanine residue, and (iii) ceramide-mimetic L-serine derivative, respectively. These glycopolymers were employed for sugar elongation reactions with glycosyl transferases such as GlcNAc beta 1,4-galactosyl transferase, beta Gal1-->3/4GlcNAc alpha-2,6-sialyl transferase, and beta Gal1-->3/4GlcNAc alpha-2,3-sialyl transferase in the presence of each sugar nucleotide as glycosyl donor to afford polymers having N-acetyllactosamine, sialyl alpha-(2-->6) N-acetyllactosamine, and sialyl alpha-(2-->3) lactose residues in excellent yield. Subsequent hydrogenolysis, hydrolysis with alpha-chymotrypsin, or transglycosylation to ceramide with ceramide glycanase proceeds smoothly to give N-acetyllactosamine, a versatile sialyl alpha-(2-->6) N-acetyllactosamine derivative having a terminal amino group, and ganglioside GM3 in high yield. (C) 1998 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)10051-9
• 作为产物：
  描述：

  对硝基苯甲醇 在 palladium on activated charcoal camphor-10-sulfonic acid 、 ammonium formate 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 甲醇 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.08h， 生成 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-[4-(6-acryloylamino-hexanoylamino)-benzyloxy]-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  High performance polymer supports for enzyme-assisted synthesis of glycoconjugates

  摘要：

  Efficient and practical methodology for the construction of carbohydrates, including oligosaccharide derivatives and sphingoglycolipids, was established on the basis of a water-soluble polymer supports having unique linkers that can be cleaved by specific conditions. Novel glycomonomers for the construction of polymer supports were synthesized and copolymerized with acrylamide to give three types of water-soluble glycopolymers having primer sugars through the specific linkers containing (i) p-substituted benzyl group, (ii) L-phenylalanine residue, and (iii) ceramide-mimetic L-serine derivative, respectively. These glycopolymers were employed for sugar elongation reactions with glycosyl transferases such as GlcNAc beta 1,4-galactosyl transferase, beta Gal1-->3/4GlcNAc alpha-2,6-sialyl transferase, and beta Gal1-->3/4GlcNAc alpha-2,3-sialyl transferase in the presence of each sugar nucleotide as glycosyl donor to afford polymers having N-acetyllactosamine, sialyl alpha-(2-->6) N-acetyllactosamine, and sialyl alpha-(2-->3) lactose residues in excellent yield. Subsequent hydrogenolysis, hydrolysis with alpha-chymotrypsin, or transglycosylation to ceramide with ceramide glycanase proceeds smoothly to give N-acetyllactosamine, a versatile sialyl alpha-(2-->6) N-acetyllactosamine derivative having a terminal amino group, and ganglioside GM3 in high yield. (C) 1998 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)10051-9

文献信息

• Chemoenzymatic oligosaccharide synthesis on a soluble polymeric carrier
  作者：Shin-Ichiro Nishimura、Koji Matsuoka、Yuan Chuan Lee

  DOI：10.1016/s0040-4039(00)77272-8

  日期：1994.8

  A facile and efficient method for the chemical and enzymatic syntheses of oligosaccharides using a new type of soluble polymeric sugar acceptor substrate is described. The water soluble glycopolymers having N-acetyl-D-glucosamine (GlcNAc) branches derived from a p-substituted benzyl glycosides were galactosylated with bovine milk galactosyl transferase. The flexible GlcNAc branches of the polymer chains allow quantitative galactosylation and subsequent hydrogenolysis proceeded smoothly to release the desired N-acetyl-lactosamine from the polymer support in high yield.