methyl 2-O-(2,3,4,-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-glucopyranoside | 3162-99-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2-O-(2,3,4,-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-glucopyranoside
• 英文别名: Methyl-2',3',4',6'-tetra-O-acetyl-α-sophorisid；Methyl-2-O-(2,3,4,6-tetra-O-methyl-β-D-glucopyranosyl)-glucosid；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-methoxyoxan-3-yl]oxyoxan-2-yl]methyl acetate
• CAS: 3162-99-0
• 化学式: C₂₁H₃₂O₁₅
• 分子量: 524.476
• InChiKey: OMACVHYHZTZIIJ-BHOWHMKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.46
• 重原子数：
  36.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  202.81
• 氢给体数：
  3.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  methyl 2-O-(2,3,4,-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-glucopyranoside 在 sodium methylate 作用下， 以85%的产率得到methyl 2-O-β-D-glucopyranosyl-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and characterisation of methyl 2-O-(β-d-glucopyranosyl)-6-O-(α-l-rhamnopyranosyl)-α-d-glucopyranoside

  摘要：

  The branched trisaccharide, 2-O-(beta-D-glucopyranosyl)-6-O-(alpha-L-rhamnopyranosyl)-D-glucopyranos e (2), is regarded as the sugar moiety of an anthocyanin pigment isolated from the fruits and flowers of certain Begonia, Clivia, Rubus, Prunus, and Ribis species. The cyanidin-3-glycoside of 1 has been identified as one of the major pigments of Montmorency cherries (Prunus cerasus). It has also been isolated as quercetin and kaempherol glycosides from the flowers of potato (Solanum tuberosum). Synthesis of the methyl glycoside of 1, methyl 2-O-(beta-D-glucopyranosyl)-6-O-(alpha-L-rhamnopyranosyl)-alpha-D-glucop yranoside (2) is reported.

  DOI：

  10.1016/0008-6215(90)84038-v
• 作为产物：
  描述：

  methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1→2)-4,6-O-benzylidene-α-D-glucopyranoside 在 三氟乙酸 作用下， 反应 0.33h， 以89%的产率得到methyl 2-O-(2,3,4,-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and characterisation of methyl 2-O-(β-d-glucopyranosyl)-6-O-(α-l-rhamnopyranosyl)-α-d-glucopyranoside

  摘要：

  The branched trisaccharide, 2-O-(beta-D-glucopyranosyl)-6-O-(alpha-L-rhamnopyranosyl)-D-glucopyranos e (2), is regarded as the sugar moiety of an anthocyanin pigment isolated from the fruits and flowers of certain Begonia, Clivia, Rubus, Prunus, and Ribis species. The cyanidin-3-glycoside of 1 has been identified as one of the major pigments of Montmorency cherries (Prunus cerasus). It has also been isolated as quercetin and kaempherol glycosides from the flowers of potato (Solanum tuberosum). Synthesis of the methyl glycoside of 1, methyl 2-O-(beta-D-glucopyranosyl)-6-O-(alpha-L-rhamnopyranosyl)-alpha-D-glucop yranoside (2) is reported.

  DOI：

  10.1016/0008-6215(90)84038-v

文献信息

• HANSMANN, CHRIS F., CARBOHYDR. RES., 204,(1990) C. 221-226
  作者：HANSMANN, CHRIS F.

  DOI：——

  日期：——