p-methoxyphenyl 2,3,6-tri-O-benzyl-α-D-mannopyranoside | 126403-23-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl 2,3,6-tri-O-benzyl-α-D-mannopyranoside
• 英文别名: (2R,3R,4S,5S,6R)-6-(4-methoxyphenoxy)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-ol
• CAS: 126403-23-4
• 化学式: C₃₄H₃₆O₇
• 分子量: 556.656
• InChiKey: VHXCUPOCGKUOOO-ZOHVZMGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 2,3,6-tri-O-benzyl-α-D-mannopyranoside 在 ammonium cerium(IV) nitrate 、 三氟甲磺酸酐 、 二苯基亚砜 作用下， 以 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 3.42h， 生成 Bn(-2)[Bn(-3)][prop-2-ynyl(-4)][Bn(-6)]Man(a1-4)[Bn(-2)][Bn(-3)][Bn(-6)]a-Man
  参考文献：
  名称：

  Synthesis of Readily Modifiable Cyclodextrin Analogues via Cyclodimerization of an Alkynyl−Azido Trisaccharide

  摘要：

  A convergent strategy for the synthesis of beta-cyclodextrin analogues is reported, utilizing preferential cyclodimerization of an azido-alkyne trisaccharide via Cu(I)-catalyzed [3 + 2] dipolar cycloaddition of the alkyne and azide functional groups. The resultant oligosaccharide macrocycle retains the binding propensity of cyclodextrins, as demonstrated by the similar ANS association constants measured for macrocycle 1 and beta-cyclodextrin. This new synthetic strategy opens up new avenues for modular preparation of functionally diverse cyclodextrin analogues that are otherwise inaccessible.

  DOI：

  10.1021/ja039374t
• 作为产物：
  描述：

  4-甲氧苯基-Alpha-D-吡喃甘露糖苷 在 三乙基硅烷 、 甲酸 、 sodium hydride 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 p-methoxyphenyl 2,3,6-tri-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of Readily Modifiable Cyclodextrin Analogues via Cyclodimerization of an Alkynyl−Azido Trisaccharide

  摘要：

  A convergent strategy for the synthesis of beta-cyclodextrin analogues is reported, utilizing preferential cyclodimerization of an azido-alkyne trisaccharide via Cu(I)-catalyzed [3 + 2] dipolar cycloaddition of the alkyne and azide functional groups. The resultant oligosaccharide macrocycle retains the binding propensity of cyclodextrins, as demonstrated by the similar ANS association constants measured for macrocycle 1 and beta-cyclodextrin. This new synthetic strategy opens up new avenues for modular preparation of functionally diverse cyclodextrin analogues that are otherwise inaccessible.

  DOI：

  10.1021/ja039374t

文献信息

• A highly stereoselective and practical synthesis of cyclomannohexaose, Cyclo{→4)-[α-d-Manp-(1→4)-]5-α-d-Manp-(1→}, a manno isomer of cyclomaltohexaose
  作者：Masato Mori、Yukishige Ito、Tomoya Ogawa

  DOI：10.1016/0008-6215(89)85173-0

  日期：1989.10

  Phenylselenyl triflate-promoted cycloglycosylation of methyl O-(2,3,6-tri-O-benzyl-α- d -mannopyranosyl)-(1→4) - [O-(2,3,6-tri-O-benzyl-α- d -mannopyranosyl)-(1→4)]4-2,3,6-tri-O-benzyl-1-thio-α- d -mannopyranoside afforded 64% of cyclo→4)-[O-(2,3,6-tri-O-benzyl-α- d -mannopyranosyl)-(1→4)]5-O-(2,3,6-tri-O-benzyl-α- d -mannopyranosyl)-(1→} which was then hydrogenolysed to give a manno isomer of cyclomaltohexaose

  摘要苯基三氟甲苯磺酸酯促进甲基O-（2,3,6-tri-O-苄基-α-d-甘露吡喃糖基）-（1→4）-[O-（2,3,6-tri-O-苄基-α-d-甘露吡喃糖基）-（（1→4）] 4-2,3,6-三-O-苄基-1-硫代-α-d-甘露糖吡喃糖苷提供64％的环→4）-[O -（2,3,6-三-O-苄基-α-d-甘露吡喃糖基）-（（1→4）] 5-O-（2,3,6-三-O-苄基-α-d-甘露糖吡喃糖基） -（1→}然后水解得到环麦芽六糖（α-环糊精）的甘露糖异构体，以立体控制的方式由3,6-二-O-苄基-4-O-氯乙酰基制备了用于环糖基化的关键甘露糖基中间体-2-Op-甲基苯甲酰基-α-d-甘露吡喃糖基三氯乙酰亚胺酸酯和对甲氧基苯基3,6-二-O-苄基-2-Op-甲基苯甲酰基-α-d-甘露吡喃糖苷。
• Synthesis of Readily Modifiable Cyclodextrin Analogues via Cyclodimerization of an Alkynyl−Azido Trisaccharide
  作者：Kyle D. Bodine、David Y. Gin、Mary S. Gin

  DOI：10.1021/ja039374t

  日期：2004.2.1

  A convergent strategy for the synthesis of beta-cyclodextrin analogues is reported, utilizing preferential cyclodimerization of an azido-alkyne trisaccharide via Cu(I)-catalyzed [3 + 2] dipolar cycloaddition of the alkyne and azide functional groups. The resultant oligosaccharide macrocycle retains the binding propensity of cyclodextrins, as demonstrated by the similar ANS association constants measured for macrocycle 1 and beta-cyclodextrin. This new synthetic strategy opens up new avenues for modular preparation of functionally diverse cyclodextrin analogues that are otherwise inaccessible.