allyl 3-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-2-phthalimido-β-D-glucopyranoside | 129354-00-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 3-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-2-phthalimido-β-D-glucopyranoside
• 英文别名: 2-[(2R,3R,4R,5S,6R)-5-hydroxy-6-[(4-methoxyphenyl)methoxymethyl]-4-phenylmethoxy-2-prop-2-enoxyoxan-3-yl]isoindole-1,3-dione
• CAS: 129354-00-3
• 化学式: C₃₂H₃₃NO₈
• 分子量: 559.616
• InChiKey: YRIMDEVJPOOZON-VPNCTUESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  41.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  103.76
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  allyl 3-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-2-phthalimido-β-D-glucopyranoside 、 4-O-Acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate 在 molecular sieve 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以27%的产率得到allyl O-(4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->4)-3-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of an appropriately protected core glycotetraoside, a key intermediate for the synthesis of “bisected” complex-type glycans of a glycoprotein

  摘要：

  A stereocontrolled synthetic route to a glycotetraoside, allyl O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-(1--- -4)-O- (3,6-di-O-allyl-2-O-benzyl-beta-D-mannopyranosyl)-(1----4)-O-3, 6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-(1----4)-3-O- benzyl- 2-deoxy-6-O-p-methoxy-phenyl-2-phthalimido-beta-D-glucopyranoside, an important intermediate for the synthesis of "bisected" complex type glycans of glycoproteins has been established by employing two glycosyl donors, 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl trichloroacetimidate and 4-O-acetyl-3,6-di-O-allyl-2-O-benzyl-alpha-D-mannopyranosyl bromide, and a glycosyl acceptor, allyl O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-(1----4) -3-O- benzyl-2-deoxy-6-O-p-methoxyphenyl-2-phthalimido-beta-D-glucopyranoside.

  DOI：

  10.1016/0008-6215(90)84222-g
• 作为产物：
  描述：

  allyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 四丁基溴化铵 、 溶剂黄146 、 三丁基氧化锡 作用下， 反应 3.5h， 生成 allyl 3-O-benzyl-2-deoxy-6-O-p-methoxybenzyl-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of an appropriately protected core glycotetraoside, a key intermediate for the synthesis of “bisected” complex-type glycans of a glycoprotein

  摘要：

  A stereocontrolled synthetic route to a glycotetraoside, allyl O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-(1--- -4)-O- (3,6-di-O-allyl-2-O-benzyl-beta-D-mannopyranosyl)-(1----4)-O-3, 6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-(1----4)-3-O- benzyl- 2-deoxy-6-O-p-methoxy-phenyl-2-phthalimido-beta-D-glucopyranoside, an important intermediate for the synthesis of "bisected" complex type glycans of glycoproteins has been established by employing two glycosyl donors, 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl trichloroacetimidate and 4-O-acetyl-3,6-di-O-allyl-2-O-benzyl-alpha-D-mannopyranosyl bromide, and a glycosyl acceptor, allyl O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-(1----4) -3-O- benzyl-2-deoxy-6-O-p-methoxyphenyl-2-phthalimido-beta-D-glucopyranoside.

  DOI：

  10.1016/0008-6215(90)84222-g

文献信息

• YAMAZAKI, FUMITO;KITAJIMA, TOHRU;NUKADA, TOMOO;ITO, YUKISHIGE;OGAWA, TOMO+, CARBOHYDR. RES. , 201,(1990) N, C. 15-30
  作者：YAMAZAKI, FUMITO、KITAJIMA, TOHRU、NUKADA, TOMOO、ITO, YUKISHIGE、OGAWA, TOMO+

  DOI：——

  日期：——