Methyl 2,4-di-O-acetyl-3,6-di-O-allyl-α-D-mannopyranoside | 146690-69-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 2,4-di-O-acetyl-3,6-di-O-allyl-α-D-mannopyranoside
• CAS: 146690-69-9
• 化学式: C₁₇H₂₆O₈
• 分子量: 358.389
• InChiKey: VYATVNNVMQHHGM-NRKLIOEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.99
• 重原子数：
  25.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Methyl 2,4-di-O-acetyl-3,6-di-O-allyl-α-D-mannopyranoside 在 sodium tetrahydroborate 、 4 A molecular sieve 、 氧气 、 臭氧 作用下， 生成 Methyl 2,4-di-O-acetyl-3,6-di-O-hydroxyethyl-α-D-mannopyranoside
  参考文献：
  名称：

  Spacer-modified trisaccharide glycosides that mimic the biantennary Asn-linked oligosaccharide acceptor of (1 → 4)-β-d-galactosyltransferase and can be used as competitive inhibitors and for irreversible deactivation

  摘要：

  The biantennary spacer-modified trisaccharide glycoside methyl 3,6-di-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyloxyethyl)-alpha-D-mannopyranoside (5) was synthesised and used together with several 2-acylamino-2-deoxy-D-glucose derivatives in competition experiments with beta-D-galactosyltransferase. CoMpound 5 was an acceptor substrate (K(M) 0.18 mM) comparable to the biantennary core heptasaccharide of glycoproteins (K(M) 0.13 mM). Replacing the N-acetyl group by other N-acyl groups did not alter the kinetic parameters significantly. When the N-acyl group was iodoacetyl, the compound was an irreversible inhibitor,

  DOI：

  10.1016/s0008-6215(00)90926-1
• 作为产物：
  描述：

  methyl 3,6-di-O-allyl-α-D-mannopyranoside 、 乙酸酐 在 吡啶 作用下， 以86%的产率得到Methyl 2,4-di-O-acetyl-3,6-di-O-allyl-α-D-mannopyranoside
  参考文献：
  名称：

  Spacer-modified trisaccharide glycosides that mimic the biantennary Asn-linked oligosaccharide acceptor of (1 → 4)-β-d-galactosyltransferase and can be used as competitive inhibitors and for irreversible deactivation

  摘要：

  The biantennary spacer-modified trisaccharide glycoside methyl 3,6-di-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyloxyethyl)-alpha-D-mannopyranoside (5) was synthesised and used together with several 2-acylamino-2-deoxy-D-glucose derivatives in competition experiments with beta-D-galactosyltransferase. CoMpound 5 was an acceptor substrate (K(M) 0.18 mM) comparable to the biantennary core heptasaccharide of glycoproteins (K(M) 0.13 mM). Replacing the N-acetyl group by other N-acyl groups did not alter the kinetic parameters significantly. When the N-acyl group was iodoacetyl, the compound was an irreversible inhibitor,

  DOI：

  10.1016/s0008-6215(00)90926-1