Dibromopentanyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->2)-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->2)-O-<(3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->3)>-6-O-(chloroacetyl)-2,4-di-O-benzyl-α-D-mannopyranoside | 143706-53-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Dibromopentanyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->2)-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->2)-O-<(3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->3)>-6-O-(chloroacetyl)-2,4-di-O-benzyl-α-D-mannopyranoside
• CAS: 143706-53-0
• 化学式: C₁₁₀H₁₁₉Br₂ClO₂₃
• 分子量: 2004.4
• InChiKey: ROGGUBHPGQIVCL-JROHTHJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.04
• 重原子数：
  136.0
• 可旋转键数：
  52.0
• 环数：
  15.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  227.97
• 氢给体数：
  0.0
• 氢受体数：
  23.0

反应信息

• 作为反应物：
  描述：

  Dibromopentanyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->2)-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->2)-O-<(3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->3)>-6-O-(chloroacetyl)-2,4-di-O-benzyl-α-D-mannopyranoside 在 碳酸氢钠 、 硫脲 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 2.0h， 以74%的产率得到Pentenyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->2)-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->2)-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)>-2,4-di-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  n-Pentenyl Mannoside Precursors for Synthesis of the Nonamannan Component of High Mannose Glycoproteins

  摘要：

  The high-mannose oligosaccharide 1 is present on the conserved V3 loop of the viral coat of HIV1 known as GP-120. The mannan portion of this molecule has been prepared by utilization of halogen-promoted n-pentenyl glycoside (NPG) coupling. Two advantageous properties of NPG's facilitated construction of 1, one being the ability to activate the donor, even when C2 esterified (i.e., ''disarmed''), with NIS/Et(3)SiOTf, under which all reactions are complete within the time required to take a TLC sample. The second advantage was the ''side-tracking'' strategy which allowed the pentenyl group of a glycosyl acceptor to be rendered temporarily inactive by conversion to the dibromide. After coupling, the ''side-tracked'' NPG could be reactivated by reductive elimination to serve as the glycosyl donor in a subsequent step. With the appropriately protected monosaccharide precursors in hand, the nonamannan could be assembled by a virtually iterative protocol involving deprotection-coupling- deprotection-coupling...etc. as the only synthetic manipulations.

  DOI：

  10.1021/jo00095a020
• 作为产物：
  描述：

  Pentenyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->2)-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside 、 Dibromopentanyl 2,4-di-O-benzyl-6-O-(chloroacetyl)-α-D-mannopyranoside 在 N-碘代丁二酰亚胺 、 三乙基硅基三氟甲磺酸酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.05h， 以72%的产率得到Dibromopentanyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->2)-O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->2)-O-<(3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->3)>-6-O-(chloroacetyl)-2,4-di-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  n-Pentenyl Mannoside Precursors for Synthesis of the Nonamannan Component of High Mannose Glycoproteins

  摘要：

  The high-mannose oligosaccharide 1 is present on the conserved V3 loop of the viral coat of HIV1 known as GP-120. The mannan portion of this molecule has been prepared by utilization of halogen-promoted n-pentenyl glycoside (NPG) coupling. Two advantageous properties of NPG's facilitated construction of 1, one being the ability to activate the donor, even when C2 esterified (i.e., ''disarmed''), with NIS/Et(3)SiOTf, under which all reactions are complete within the time required to take a TLC sample. The second advantage was the ''side-tracking'' strategy which allowed the pentenyl group of a glycosyl acceptor to be rendered temporarily inactive by conversion to the dibromide. After coupling, the ''side-tracked'' NPG could be reactivated by reductive elimination to serve as the glycosyl donor in a subsequent step. With the appropriately protected monosaccharide precursors in hand, the nonamannan could be assembled by a virtually iterative protocol involving deprotection-coupling- deprotection-coupling...etc. as the only synthetic manipulations.

  DOI：

  10.1021/jo00095a020

文献信息

• n-Pentenyl glycoside methodology for rapid assembly of homoglycans exemplified with the nonasaccharide component of a high-mannose glycoprotein
  作者：J. Robert Merritt、Bert Fraser-Reid

  DOI：10.1021/ja00047a080

  日期：1992.10