phenyl 6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1-thio-β-D-mannopyranoside | 246875-57-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1-thio-β-D-mannopyranoside
• 英文别名: (3aS,4S,6R,7R,7aS)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-4-phenylsulfanyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-7-ol
• CAS: 246875-57-0
• 化学式: C₃₁H₃₈O₅SSi
• 分子量: 550.791
• InChiKey: KXWKAUBGGGPLRN-PNHLWVRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.96
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  82.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenyl 6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1-thio-β-D-mannopyranoside 在 吡啶 、 四丁基氟化铵 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 28.0h， 生成 phenyl 4,6-di-O-acetyl-1-thio-β-D-mannopyranoside
  参考文献：
  名称：

  A Practical Route to Multifunctional 2-Azido-2-deoxy-d-glucopyranosyl Donors

  摘要：

  DOI：

  10.1021/jo990811p
• 作为产物：
  描述：

  phenyl 1-thio-β-D-mannopyranoside 在 camphor-10-sulfonic acid 作用下， 以 吡啶 、 丙酮 为溶剂， 反应 24.17h， 生成 phenyl 6-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-1-thio-β-D-mannopyranoside
  参考文献：
  名称：

  A Practical Route to Multifunctional 2-Azido-2-deoxy-d-glucopyranosyl Donors

  摘要：

  DOI：

  10.1021/jo990811p

文献信息

• Total Synthesis of a Conjugation-Ready Tetrasaccharide Repeating Unit of <i>Vibrio cholerae</i> O:3 O-antigen Polysaccharide
  作者：Soumyakanta Maji、Balasaheb K. Ghotekar、Suvarn S. Kulkarni

  DOI：10.1021/acs.orglett.3c04225

  日期：2024.1.26

  Herein, we report the first total synthesis of the tetrasaccharide repeating unit of Vibrio cholerae O:3 O-antigen polysaccharide. The highly complex tetrasaccharide contains rare amino sugars such as d-bacillosamine and l-fucosamine, highly labile sugar ascarylose, and higher carbon sugar d-d-heptose. Stereoselective glycosylation of the notoriously reactive ascarylose with d-d-heptose, poor nucleophilicity

  在此，我们报道了霍乱弧菌O:3 O-抗原多糖四糖重复单元的首次全合成。高度复杂的四糖含有稀有氨基糖，如d-芽孢杆菌胺和l-岩藻糖胺、高度不稳定的糖蛔糖和高碳糖d - d-庚糖。臭名昭著的活性蛔糖与d - d-庚糖的立体选择性糖基化、 l-岩藻糖胺的轴向C4-OH亲核性差以及酰胺偶联是全合成中遇到的关键挑战，该合成是通过最长的23线性序列完成的总收益率达到 4.2%。
• Stereoselectivity of glycosylations of conformationally restricted mannuronate esters
  作者：Jeroen D.C. Codée、Ana R. de Jong、Jasper Dinkelaar、Herman S. Overkleeft、Gijsbert A. van der Marel

  DOI：10.1016/j.tet.2009.02.067

  日期：2009.5

  Glycosidation of conformationally unrestricted mannuronate ester donors proceeds in a highly P-selective fashion, whereas condensations of mannuronate ester donors, which are con formationally constrained by a 3,4-butanedimethylacetal or a 2,3-isopropylidene function, provide a-selective products. We hypothesize that the difference in stereochemical outcome of these condensations results from the different conformations of the product forming oxacarbenium intermediate. The formation of the beta-linked products from the flexible mannuronates is thought to originate from the most favorable H-3(4) oxacarbenium ion, which is not accessible from the conformationally restrained donors. Although an a-triflate intermediate is formed upon activation of the 3,4-butanedimethylacetal protected mannuronate ester thio donor, this is not the product forming intermediate. The anomeric triflate serves as a reservoir for the H-4(3) oxacarbenium ion, which is glycosidated to provide the a-linked mannuronates. (C) 2009 Elsevier Ltd. All rights reserved.