Toluene-4-sulfonic acid (3aS,4R,6R,7R,7aS)-6-methoxy-7-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethyl ester | 182167-61-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Toluene-4-sulfonic acid (3aS,4R,6R,7R,7aS)-6-methoxy-7-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethyl ester
• CAS: 182167-61-9
• 化学式: C₂₅H₃₂O₉S
• 分子量: 508.59
• InChiKey: KGENGIYAAFJADN-OYTPZHDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  35.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  98.75
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  Toluene-4-sulfonic acid (3aS,4R,6R,7R,7aS)-6-methoxy-7-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethyl ester 在 吡啶 、 盐酸 、 ruthenium trichloride 、 sodium periodate 、 lithium aluminium tetrahydride 、 氯化亚砜 、 iodonium di(2,4,6-collidinium) triflate 、 4 A molecular sieve 、 硫酸 、 potassium tert-butylate 、 四丁基碘化铵 、 tetrabutylammonium borohydride 、 溶剂黄146 、 zinc(II) iodide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 乙酸乙酯 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 51.9h， 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 、 4-甲氧基氯苄 在 四丁基碘化铵 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 以88%的产率得到Toluene-4-sulfonic acid (3aS,4R,6R,7R,7aS)-6-methoxy-7-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethyl ester
  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