Methyl 2-O-(p-methoxybenzyl)-3,4-O-sulfonyl-β-D-fucopyranoside | 182167-65-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Methyl 2-O-(p-methoxybenzyl)-3,4-O-sulfonyl-β-D-fucopyranoside
• 英文别名: (3aS,4R,6R,7R,7aR)-6-methoxy-7-[(4-methoxyphenyl)methoxy]-4-methyl-4,6,7,7a-tetrahydro-3aH-[1,3,2]dioxathiolo[4,5-c]pyran 2,2-dioxide
• CAS: 182167-65-3
• 化学式: C₁₅H₂₀O₈S
• 分子量: 360.385
• InChiKey: NYEFEKUCIIICEL-FDHZTJNISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  97.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Methyl 2-O-(p-methoxybenzyl)-3,4-O-sulfonyl-β-D-fucopyranoside 在 吡啶 、 盐酸 、 iodonium di(2,4,6-collidinium) triflate 、 4 A molecular sieve 、 硫酸 、 potassium tert-butylate 、 四丁基碘化铵 、 tetrabutylammonium borohydride 、 zinc(II) iodide 作用下， 以 甲醇 、 乙醚 、 1,2-二氯乙烷 为溶剂， 反应 27.9h， 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：

  methyl 3,4-O-isopropylidene-6-O-tosyl-β-D-galactopyranoside 在 吡啶 、 ruthenium trichloride 、 sodium periodate 、 lithium aluminium tetrahydride 、 氯化亚砜 、 四丁基碘化铵 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 26.5h， 生成 Methyl 2-O-(p-methoxybenzyl)-3,4-O-sulfonyl-β-D-fucopyranoside
  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.