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 | 143706-52-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 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
• 英文别名: 4-pentenyl 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-mannopyranoside；[(2R,3S,4S,5R,6R)-2-[(2R,3S,4S,5R,6R)-2-[(2S,3S,4S,5R,6R)-2-pent-4-enoxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 143706-52-9
• 化学式: C₈₈H₉₆O₁₇
• 分子量: 1425.72
• InChiKey: XGPYIOUHLUXDOA-JJHWJILXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.4
• 重原子数：
  105
• 可旋转键数：
  41
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  165
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为反应物：
  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
• 作为产物：
  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)-3,4,6-tri-O-benzyl-α-D-mannopyranoside 在 四丁基碘化铵 、 锌 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 以95%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)-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

• Solid-Phase Oligosaccharide Synthesis:  Preparation of Complex Structures Using a Novel Linker and Different Glycosylating Agents
  作者：Rodrigo B. Andrade、Obadiah J. Plante、Luis G. Melean、Peter H. Seeberger

  DOI：10.1021/ol991071+

  日期：1999.12.1

  [formula: see text] A beta-(1-->4)-linked trisaccharide was prepared in 53% yield on a polymer support using glycosyl phosphates and released by cross-metathesis of a novel linker to reveal the anomeric n-pentenyl glycoside. Heptasaccharide 33 was prepared in 9% yield in 14 steps.

  [公式：参见文本]使用糖基磷酸酯在聚合物载体上以53％的收率制备β-（1-> 4）连接的三糖，并通过新型连接子的复分解而释放，从而揭示异头正戊烯糖苷。通过14个步骤以9％的产率制备七糖33。
• “Cap-Tag”—Novel Methods for the Rapid Purification of Oligosaccharides Prepared by Automated Solid-Phase Synthesis Financial support from the donors of the Petroleum Research Fund, administered by the ACS (ACS-PRF 34649-G1), Merck (Predoctoral Fellowship for E.R.P.), Boehringer-Ingelheim (Predoctoral Fellowship for E.R.P.), and the NIH (Biotechnology Training Grant for M.C.H.) is gratefully acknowledged. Funding for the MIT-DCIF Inova 501 was provided by the NSF (Award CHE-9808061). Funding for the MIT-DCIF Avance (DPX) 400 was provided by the NIH (Award 1S10RR13886-01). We thank Silicycle (Quebec City, Canada) for the generous gift of fluorous silica gel and isocyanate silica gel scavenger resin. We thank Dr. O. Plante for helpful discussions and help with the automated oligosaccharide synthesizer.
  作者：Emma R. Palmacci、Michael C. Hewitt、Peter H. Seeberger

  DOI：10.1002/1521-3773(20011203)40:23<4433::aid-anie4433>3.0.co;2-8

  日期：2001.12.3
• 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