pent-4-enyl 2-O-(3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside | 150772-63-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: pent-4-enyl 2-O-(3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside
• 英文别名: (2R,3S,4R,5R,6R)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-[(2S,3S,4S,5R,6R)-2-pent-4-enoxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]oxy-4,5-bis(phenylmethoxy)oxan-3-ol
• CAS: 150772-63-7
• 化学式: C₆₈H₇₈O₁₁Si
• 分子量: 1099.45
• InChiKey: GETYKSBAFBUOQV-STOLNPSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.3
• 重原子数：
  80
• 可旋转键数：
  29
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-benzyl-β-D-mannopyranose 1,2-(pent-4-enyl orthobenzoate) 、 pent-4-enyl 2-O-(3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside 在 N-碘代丁二酰亚胺 、 ytterbium(III) triflate 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到pent-4-enyl O-(2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1-2)-O-(3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-α-D-mannopyranosyl)-(1-2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  A Strategy for Ready Preparation of Glycolipids for Multivalent Presentation

  摘要：

  The olefinic residue of a-pentenyl glycosides serves as the trigger for regioselective construction of higher saccharides and then for elaboration in multivalent glycolipids.

  DOI：

  10.1021/ol0511981
• 作为产物：
  描述：

  3,4,6-tri-O-benzyl-β-D-mannopyranose 1,2-(pent-4-enyl orthobenzoate) 在 4 A molecular sieve 、 sodium methylate 、 silver trifluoromethanesulfonate 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 pent-4-enyl 2-O-(3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-α-D-mannopyranosyl)-3,4,6-tri-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  A ready, convergent synthesis of the heptasaccharide GPI membrane anchor of rat brain Thy-1 glycoprotein

  摘要：

  DOI：

  10.1021/ja00070a048

文献信息

• Studies Related to Synthesis of Glycophosphatidylinositol Membrane-Bound Protein Anchors. 5. n-Pentenyl Ortho Esters for Mannan Components
  作者：Carmichael Roberts、Robert Madsen、Bert Fraser-Reid

  DOI：10.1021/ja00110a010

  日期：1995.2

  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.
• A Strategy for Ready Preparation of Glycolipids for Multivalent Presentation
  作者：Jun Lu、Bert Fraser-Reid、Channe Gowda

  DOI：10.1021/ol0511981

  日期：2005.9.1

  The olefinic residue of a-pentenyl glycosides serves as the trigger for regioselective construction of higher saccharides and then for elaboration in multivalent glycolipids.
• A ready, convergent synthesis of the heptasaccharide GPI membrane anchor of rat brain Thy-1 glycoprotein
  作者：Uko E. Udodong、Robert Madsen、Carmichael Roberts、Bert Fraser-Reid

  DOI：10.1021/ja00070a048

  日期：1993.8