Dibromopentanyl O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside | 157253-28-6

• 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: Dibromopentanyl O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside
• 英文别名: (2R,3S,4R,5R,6R)-2-[(2S,3S,4S,5R,6R)-2-(4,5-dibromopentoxy)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol
• CAS: 157253-28-6
• 化学式: C₅₉H₆₆Br₂O₁₁
• 分子量: 1110.97
• InChiKey: YACVOBMVAARKRX-XDXJDSHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.7
• 重原子数：
  72
• 可旋转键数：
  28
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.39
• 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：

  4-penten-1-yl 2-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranoside 、 Dibromopentanyl O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-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70%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)-3,4,6-tri-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：

  4,5-dibromopentanyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside 在 N-碘代丁二酰亚胺 、 氨 、 三乙基硅基三氟甲磺酸酯 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 96.05h， 生成 Dibromopentanyl O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->2)-3,4,6-tri-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 Mannoside Precursors for Synthesis of the Nonamannan Component of High Mannose Glycoproteins
  作者：J. Robert Merritt、Elizabeth Naisang、Bert Fraser-Reid

  DOI：10.1021/jo00095a020

  日期：1994.8

  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.