pent-4-enyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1→2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside | 123487-61-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: pent-4-enyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1→2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside
• 英文别名: [(2R,3R,4S,5S,6R)-3,4,5-tribenzoyloxy-6-[(2S,3S,4S,5R,6R)-2-pent-4-enoxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl benzoate
• CAS: 123487-61-6
• 化学式: C₆₆H₆₄O₁₅
• 分子量: 1097.23
• InChiKey: GEKZFBJQDFBNKN-RUJDOBNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.73
• 重原子数：
  81.0
• 可旋转键数：
  26.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  169.81
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  pent-4-enyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1→2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以74%的产率得到
  参考文献：
  名称：

  Access to n-pentenyl tetra- and pentasaccharide analogues of the antitumor drug PI-88 based on 1,2-methyl orthoester glycosyl donors

  摘要：

  DOI：

  10.1016/j.carres.2022.108557
• 作为产物：
  描述：

  2,3,4,6-Tetra-O-benzoyl-α-D-mannopyranosyl bromide 、 pent-4-enyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside 在 4 A molecular sieve 、 silver trifluoromethanesulfonate 、 1,1,3,3-四甲基脲 作用下， 生成 pent-4-enyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl-(1→2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Studies Related to Synthesis of Glycophosphatidylinositol Membrane-Bound Protein Anchors. 5. n-Pentenyl Ortho Esters for Mannan Components

  摘要：

  Procedures for rapid assembly of multigram amounts of mannan components have been examined. Although these studies are reported in the context of the mannan moiety of the glycan anchors of membrane-bound glycoproteins, the procedures should be applicable to the wider family of mannose-containing glycoproteins. Readily prepared n-pentenyl ortho esters of mannose are shown to be versatile substrates that can serve as glycosyl donors in their own right or be used to furnish mannosyl bromides or n-pentenyl alpha-D-mannosides. Thus three glycosyl donors of different reactivities and stabilities are obtainable from the same precursor, all three being activated under mild conditions. Two approaches are described. in the first, a portion of the starting n-pentenyl ortho ester is converted into an n-pentenyl glycoside (NPG) by acid-catalyzed rearrangement, while another portion is titrated with bromine to give a glycosyl bromide. These are coupled under Koenigs-Knorr conditions to give an n-pentenyl disaccharide which is then processed to become a glycosyl acceptor. A third portion of the ortho ester, after suitable protecting group adjustments, is also titrated with bromine and coupled to the disaccharide acceptor to give the desired trimannan. The instability of glycosyl bromides detracts from this route, and so a second approach which avoids their use completely was pursued in which NPG obtained from the acid-catalyzed rearrangement was converted into a vicinal dibromide. The latter is then able to serve as a glycosyl acceptor for coupling to a donor obtainable by reaction of the n-pentenyl ortho ester with halonium ion. The dibromopentanyl disaccharide produced then becomes an acceptor for a donor derived from n-pentenyl mannoside. The second approach uses no unstable reactants, is therefore experimentally less demanding, and can be operated conveniently on a large scale.

  DOI：

  10.1021/ja00110a010

文献信息

• n-Pentenyl glycosides facilitate a stereoselective synthesis of the pentasaccharide core of the protein membrane anchor found in Trypanosoma brucei
  作者：David R. Mootoo、Peter Konradsson、Bert Fraser-Reid

  DOI：10.1021/ja00204a049

  日期：1989.10
• Studies Related to Synthesis of Glycophosphatidylinositol Membrane-Bound Protein Anchors. 6. Convergent Assembly of Subunits
  作者：Robert Madsen、Uko E. Udodong、Carmichael Roberts、David R. Mootoo、Peter Konradsson、Bert Fraser-Reid

  DOI：10.1021/ja00110a011

  日期：1995.2

  Glycophosphatidylinositol anchors of membrane-bound proteins are thought to comprise a common pentasaccharide core containing mannan, glucosamine, and inositol residues. A synthetic route to this core is described. In addition, the complete heptasaccharide moiety of the rat brain Thy-1 membrane anchor, the first mammalian membrane anchor to be characterized, has been synthesized. In the case of the Thy-1 anchor, the synthetic plan is based on three building blocks comprising glucosamine-inositol, galactosamine-mannose, and trimannan residues. Although glycosyl donors other than n-pentenyl glycosides (NPGs) have been used in preparing each of these building blocks, the final assembly of the heptasaccharide utilizes NPGs as the only glycosyl donors. The mildness of the conditions for these coupling reactions has allowed us to make provisions for subsequent installation of the three phosphodiester units.
• MOOTOO, DAVID R.;KONRADSSON, PETER;FRASER-REID, BERT, J. AMER. CHEM. SOC., 111,(1989) N2, C. 8540-8542
  作者：MOOTOO, DAVID R.、KONRADSSON, PETER、FRASER-REID, BERT

  DOI：——

  日期：——