Allyl 2-O-benzoyl-3-O-[4-O-benzoyl-3,6-dideoxy-2-O-(p-methoxybenzyl)-α-D-xylo-hexopyranosyl]-4,6-di-O-(p-methoxybenzyl)-α-D-mannopyranoside | 182167-88-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Allyl 2-O-benzoyl-3-O-[4-O-benzoyl-3,6-dideoxy-2-O-(p-methoxybenzyl)-α-D-xylo-hexopyranosyl]-4,6-di-O-(p-methoxybenzyl)-α-D-mannopyranoside
• 英文别名: Mob(-2)[Bz(-4)]Abe(a1-3)[Bz(-2)][Mob(-4)][Mob(-6)]Man(a)-O-allyl；[(2R,3R,5R,6R)-6-[(2R,3R,4S,5S,6S)-5-benzoyloxy-3-[(4-methoxyphenyl)methoxy]-2-[(4-methoxyphenyl)methoxymethyl]-6-prop-2-enoxyoxan-4-yl]oxy-5-[(4-methoxyphenyl)methoxy]-2-methyloxan-3-yl] benzoate
• CAS: 182167-88-0
• 化学式: C₅₃H₅₈O₁₄
• 分子量: 919.035
• InChiKey: OYEMTDZWTQWUOE-NVNSOXBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  67
• 可旋转键数：
  24
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  145
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  Allyl 2-O-benzoyl-3-O-[4-O-benzoyl-3,6-dideoxy-2-O-(p-methoxybenzyl)-α-D-xylo-hexopyranosyl]-4,6-di-O-(p-methoxybenzyl)-α-D-mannopyranoside 在 盐酸 、 potassium tert-butylate 作用下， 以 甲醇 为溶剂， 反应 19.75h， 生成 allyl 3-O-(3,6-dideoxy-α-D-xylo-hexapyranosyl)-α-D-mannopyranoside
  参考文献：
  名称：

  Preparation of Disaccharide Haptens Corresponding toSalmonellaSerogroups B and D

  摘要：

  The properly protected ethyl 1-thio-abequopyranoside 11 and ethyl 1-thio-tyvelo-pyranoside 26 were prepared by a sequence of reactions, the key step of which was the regioselective hydride-mediated ring-opening of the cyclic sulfate function in compounds 8 and 18. Iodonium ion-assisted glycosylation of allyl mannopyranoside 30 with the individual ethyl 3,6-dideoxy-1-thio-D-hexopyranoside donors 11 and 26 furnished, after deprotection, the respective allyl 3-O-(alpha-D-abequopyranosyl)-alpha-D-mannopyranoside 1 and allyl 3-O-(alpha-D-tyvelopyranosyl)-alpha-D-mannopyranoside 2.

  DOI：

  10.1080/07328309608005684
• 作为产物：
  描述：

  allyl 2,3-O-isopropylidene-α-D-mannopyranoside 在 iodonium di(2,4,6-collidinium) triflate 、 4 A molecular sieve 、 sodium hydride 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 5.75h， 生成 Allyl 2-O-benzoyl-3-O-[4-O-benzoyl-3,6-dideoxy-2-O-(p-methoxybenzyl)-α-D-xylo-hexopyranosyl]-4,6-di-O-(p-methoxybenzyl)-α-D-mannopyranoside
  参考文献：
  名称：

  Preparation of Disaccharide Haptens Corresponding toSalmonellaSerogroups B and D

  摘要：

  The properly protected ethyl 1-thio-abequopyranoside 11 and ethyl 1-thio-tyvelo-pyranoside 26 were prepared by a sequence of reactions, the key step of which was the regioselective hydride-mediated ring-opening of the cyclic sulfate function in compounds 8 and 18. Iodonium ion-assisted glycosylation of allyl mannopyranoside 30 with the individual ethyl 3,6-dideoxy-1-thio-D-hexopyranoside donors 11 and 26 furnished, after deprotection, the respective allyl 3-O-(alpha-D-abequopyranosyl)-alpha-D-mannopyranoside 1 and allyl 3-O-(alpha-D-tyvelopyranosyl)-alpha-D-mannopyranoside 2.

  DOI：

  10.1080/07328309608005684

文献信息

• Preparation of Disaccharide Haptens Corresponding to<i>Salmonella</i>Serogroups B and D
  作者：Korien Zegelaar-Jaarsveld、Simon C. van der Plas、Gijs A. van der Marel、Jacques H. van Boom

  DOI：10.1080/07328309608005684

  日期：1996.8

  The properly protected ethyl 1-thio-abequopyranoside 11 and ethyl 1-thio-tyvelo-pyranoside 26 were prepared by a sequence of reactions, the key step of which was the regioselective hydride-mediated ring-opening of the cyclic sulfate function in compounds 8 and 18. Iodonium ion-assisted glycosylation of allyl mannopyranoside 30 with the individual ethyl 3,6-dideoxy-1-thio-D-hexopyranoside donors 11 and 26 furnished, after deprotection, the respective allyl 3-O-(alpha-D-abequopyranosyl)-alpha-D-mannopyranoside 1 and allyl 3-O-(alpha-D-tyvelopyranosyl)-alpha-D-mannopyranoside 2.