benzyl 3,4-di-O-benzyl-α-D-mannopyranoside | 80859-30-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 3,4-di-O-benzyl-α-D-mannopyranoside
• 英文别名: (2S,3S,4R,5R,6R)-6-(hydroxymethyl)-2,4,5-tris(phenylmethoxy)oxan-3-ol
• CAS: 80859-30-9
• 化学式: C₂₇H₃₀O₆
• 分子量: 450.532
• InChiKey: QIHJRJJMIHBYFK-NTYGKXENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl 3,4-di-O-benzyl-α-D-mannopyranoside 在 palladium on activated charcoal 2,4,6-三甲基吡啶 、 氢气 、 sodium methylate 、 silver trifluoromethanesulfonate 、 一水合肼 作用下， 以 吡啶 、 甲醇 、 乙醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 生成 2,6-di-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-β-D-mannose
  参考文献：
  名称：

  合成形成糖蛋白碳水化合物部分复杂类型一部分的三种寡糖。

  摘要：

  三氟甲磺酸银促进的3,4,6-三-O-乙酰基-2-脱氧-2-邻苯二甲酰亚胺-β-D-吡喃葡萄糖基溴化物与3,6-二-O-苄基-α-D-甘露吡喃糖苷和苄基3,4-二-O-苄基-α-D-甘露吡喃糖苷以54％和32％的产率得到被保护的2,4-和2,6-连接的三糖。将2-deoxy-2-phthalimido基团换成2-acetamido-2-deoxy基团并进行脱保护后，三糖2,4-di-O-（2-deoxy-beta-D-吡喃葡萄糖基）-D-甘露糖得到2，6-二-O-（2-乙酰胺基-2-脱氧β-D-吡喃葡萄糖基）-D-甘露糖。3,6-二-O-乙酰基-2-脱氧-2-邻苯二甲酰亚胺-4-O-（2,3,4,6-四-O-乙酰基-β-D-吡喃半乳糖基）-β-D的类似缩合-吡喃葡萄糖基溴化物与苄基3，4-二-O-苄基-α-D-甘露吡喃糖苷一起以52％的收率得到五糖衍生物。

  DOI：

  10.1016/s0008-6215(00)80676-x
• 作为产物：
  描述：

  2,6-di-O-acetyl-3,4-di-O-benzyl-α-D-mannopyranosyl bromide 在 4 A molecular sieve 、 sodium methylate 、 氰化汞 、 mercury dibromide 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 19.0h， 生成 benzyl 3,4-di-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  合成烯类N-乙酰神经氨酸盐-合成氢嵌段。Kupplung zum N-乙酰神经氨酸半透明糖蜜三甲基甲硅烷基三氟甲磺酸

  摘要：

  摘要获得了由N-乙酰神经氨酸和乳糖胺组成的三糖合成嵌段，该嵌段可与其他糖单元进行一般偶联反应。O-（5-乙酰氨基-4,7,8,9-四-甲基-O-乙酰基-3,5-二脱氧-α-和-β-d-甘油-d-半乳清-2-壬基吡喃二磺酸酯）-（2→ 6）-O-（2,3,4-三-O-乙酰基-β-d-吡喃半乳糖基）-（1→4）-1,3,6-三-O-乙酰基-2-脱氧-2-邻苯二甲酰亚胺基-β-d-吡喃葡萄糖被用作糖基供体。在三甲基甲硅烷基三氟甲基磺酸盐的存在下，通过与在OH-2处代表糖基受体的未取代的d-甘露糖衍生物反应，将两种化合物转化为四糖。除去保护基团得到O-（5-乙酰氨基-3，

  DOI：

  10.1016/s0008-6215(00)90670-0

文献信息

• Ditritylation of Methyl and Benzyl α-D-Gluco-, -Manno-, and -Galactopyranosides and Preparation of Their Partially Benzylated Derivatives
  作者：Shinkiti Koto、Naohiko Morishima、Toyosaku Yoshida、Masaharu Uchino、Shonosuke Zen

  DOI：10.1246/bcsj.56.1171

  日期：1983.4

  The ditritylation of methyl and benzyl α-D-gluco-, -manno-, and -galactopyranosides with trityl chloride in pyridine at 70 °C proceeds in a regioselective manner to give the 2,6-ditrityl ethers of the glucosides, the 3,6-ones of the mannosides, and both 2,6- and 3,6-ones of the galactosides. The rearrangement of the trityl group from O-3 to O-2 of the mannosides at 100 °C causes the selective formation

  甲基和苄基 α-D-葡糖-、-甘露糖-和-吡喃半乳糖苷与三苯甲基氯在 70 °C 的吡啶中以区域选择性方式进行二三苯甲基化，得到葡萄糖苷的 2,6-二三苯甲基醚，即 3,甘露糖苷的 6 个，以及半乳糖苷的 2,6-和 3,6-一个。在 100 °C 时，甘露糖苷的三苯甲基从 O-3 重排为 O-2，导致 2,6-二三苯甲基醚的选择性形成。由2,6-和3,6-二三苯甲基醚制备吡喃己糖苷的3,4-和2,4-二苄基醚。
• Synthesis of Multiantennary Complex Type<i>N</i>-Glycans by Use of Modular Building Blocks
  作者：Carlo Unverzagt、Gislinde Gundel、Steffen Eller、Ralf Schuberth、Joachim Seifert、Harald Weiss、Math��us Niemietz、Matthias Pischl、Claudia Raps

  DOI：10.1002/chem.200901908

  日期：2009.11.16

  developed for the synthesis of multiantennary N‐glycans of the complex type, which are commonly found on glycoproteins. The donor building blocks were laid out for the elongation of a core trisaccharide acceptor (β‐mannosyl chitobiose) conveniently protected with a single benzylidene moiety at the β‐mannoside. Through two consecutive regio‐ and stereoselective couplings the donors gave N‐glycans with three

  开发了一组模块化的寡糖构建基块，用于合成复杂类型的多天线N聚糖，这些糖通常在糖蛋白上发现。布置了供体结构单元，以延长核心三糖受体（β-甘露糖基壳二糖）的延伸，该受体方便地由β-甘露糖苷上的单个亚苄基部分保护。通过两个连续的区域和立体选择性偶联，供体以高产量获得了具有三到五个触角的N-聚糖。由于供体的保护基图案一致，可以通过使用一般的反应顺序对最终产物进行脱保护。
• Glycosylation Using Hemiacetal Sugar Derivatives: Synthesis of<i>O</i>-α-D-Rhamnosyl-(1→3)-<i>O</i>-α-D-rhamnosyl-(1→2)-d-rhamnose and<i>O</i>-α-D-Tyvelosyl-(1→3)-<i>O</i>-α-D-mannosyl-(1→4)-L-rhamnose
  作者：Motoko Hirooka、Asako Yoshimura、Izumi Saito、Fumio Ikawa、Yoko Uemoto、Shinkiti Koto、Ayano Takabatake、Aya Taniguchi、Yoshika Shinoda、Aya Morinaga

  DOI：10.1246/bcsj.76.1409

  日期：2003.7

  O-α-D-Rhamnopyranosyl-(1→3)-O-α-D-rhamnopyranosyl-(1→2)-D-rhamnopyranose, a repeating trisaccharide of the O-specific polysaccharides (OPSs) of Pseudomonades, and O-α-D-tyvelopyranosyl-(1→3)-O-α-D-mannopyranosyl-(1→4)-L-rhamnopyranose, a trisaccharide composing the OPSs of Salmonella typhi, were synthesized by in-situ activating glycosylation reactions using hemiacetal sugar derivatives. Allyl 2,4-di-O-

  O-α-D-吡喃鼠李糖基-(1→3)-O-α-D-吡喃鼠李糖基-(1→2)-D-吡喃鼠李糖，假单胞菌的 O-特异性多糖 (OPS) 的重复三糖，和 O- α-D-tyvelopyranosyl-(1→3)-O-α-D-mannopyranosyl-(1→4)-L-rhamnopyranosyl-(1→4)-L-rhamnopyranose 是组成伤寒沙门氏菌 OPS 的三糖，通过使用半缩醛原位激活糖基化反应糖衍生物。烯丙基 2,4-二-O-苄基-α-D-吡喃鼠李糖苷是通过烯丙基 α-D-吡喃甘露糖苷的直接二三苯甲基化制备的。3-O-Acetyl-2,4-di-O-benzyl-D-rhamnopyranose 用作 D-tyvelose（3,6-dideoxy-D-arabino-hexose, 3,6-dideoxy- D-mannopyranose, 3-deoxy-D-rhamnose)
• Jayaprakash; Fraser-Reid, Bert, Organic Letters, 2004, vol. 6, # 23, p. 4211 - 4214
  作者：Jayaprakash、Fraser-Reid, Bert

  DOI：——

  日期：——
• Efficient Chemical Synthesis of a Dodecasaccharidyl Lipomannan Component of Mycobacterial Lipoarabinomannan
  作者：Bert Fraser-Reid、Siddhartha Ray Chaudhuri、K. N. Jayaprakash、Jun Lu、Changalvala V. S. Ramamurty

  DOI：10.1021/jo802000p

  日期：2008.12.19

  Lipomannan (LM) is one of the domains of lipoarabinomannan (LAM) glycolipids, the latter being one of several cell surface organic molecules that fortify mycobacterial species against external attack. Some members of mycobacterial families are pathogenic, most notably Mycobacterium tuberculosis and Mycobacterium leprae, while others are nonpathogenic, and used in the clinic, such as Mycobacterium smegmatis. Additional biological significance arises from the fact that LM has been implicated in several health disorders outside of those associated with mycobacterial pathogens, notably for treatment of bladder cancer. LM is comprised of a heavily lipidated phosphoinositide dimannoside headgroup, from which a mannan array, of varied complexity, extends. The latter consists of a 1,6-alpha-linked backbone flanked at position O2, not necessarily regularly, with alpha-linked mannosides. This paper gives an example of lipomannan synthesis in which all of the sugar components, whether functioning as donors or acceptors, are obtained from n-pentenyl orthoesters, themselves in turn prepared in three easy steps from D-mannose. Assembly of the mannan array is facilitated by the exquisite regioselectivity occasioned by the use of ytterbium triflate/N-iodosuccinimide as the trigger for reaction of n-pentenyl orthoesters.