1,2-O-ethylidene-(R,S)-β-D-mannopyranose | 230953-16-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 1,2-O-ethylidene-(R,S)-β-D-mannopyranose
• 英文别名: 1,2-O-Ethylidene-β-D-mannopyranose；1,2-ethylidene-β-D-mannopyranoside；(3aS,5R,6S,7S,7aS)-5-(hydroxymethyl)-2-methyl-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-6,7-diol
• CAS: 230953-16-9
• 化学式: C₈H₁₄O₆
• 分子量: 206.196
• InChiKey: GXGDQLJREOZCHI-UFUXXVNNSA-N

物化性质

• 熔点：
  115-117°C
• 溶解度：
  甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2-O-ethylidene-(R,S)-β-D-mannopyranose 在 4 A molecular sieve 、 三氟化硼乙醚 、 sodium acetate 、 silver trifluoromethanesulfonate 、 (+)-10-camphorsulfonic acid 、 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 102.67h， 生成 allyl 2,4,6-tri-O-acetyl-3-O-(2',3',4',6'-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of carbosilane dendrimers having peripheral mannose and mannobiose

  摘要：

  The mannose monosaccharide derivative, acetylthiopropyl 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranoside (Man), and the mannobiose derivative, acetylthiopropyl 2,4,6-tri-O-acetyl-3-O-(2,3',4',6'-tetra-O-acetyl-alpha-D-mannopyranosyl)-alpha-D-mannopyranoside (alpha-1,3-Man), were synthesized respectively. These mannose derivatives were introduced into carbosilane dendrimer scaffolds of the zero and first generations. As a result, six carbosilane dendrimers were functionalized by Man and alpha-1,3-Man. Isothermal titration microcalorimetry was done to determine binding assay between mannose moieties of carbosilane dendrimer and concanavalin A. It was found that carbosilane dendrimers bound more efficiently to concanavalin A than free mannose (Me-alpha-Man) and mannobiose (Me-alpha-1,3-' Man). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.090
• 作为产物：
  描述：

  2,3,4,6-四-O-乙酰基-1-溴-Alpha-D-甘露糖 在 sodium tetrahydroborate 、 sodium methylate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 23.0h， 生成 1,2-O-ethylidene-(R,S)-β-D-mannopyranose
  参考文献：
  名称：

  Synthesis of carbosilane dendrimers having peripheral mannose and mannobiose

  摘要：

  The mannose monosaccharide derivative, acetylthiopropyl 2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranoside (Man), and the mannobiose derivative, acetylthiopropyl 2,4,6-tri-O-acetyl-3-O-(2,3',4',6'-tetra-O-acetyl-alpha-D-mannopyranosyl)-alpha-D-mannopyranoside (alpha-1,3-Man), were synthesized respectively. These mannose derivatives were introduced into carbosilane dendrimer scaffolds of the zero and first generations. As a result, six carbosilane dendrimers were functionalized by Man and alpha-1,3-Man. Isothermal titration microcalorimetry was done to determine binding assay between mannose moieties of carbosilane dendrimer and concanavalin A. It was found that carbosilane dendrimers bound more efficiently to concanavalin A than free mannose (Me-alpha-Man) and mannobiose (Me-alpha-1,3-' Man). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.090

文献信息

• Highly Regio- and Stereoselective Synthesis of Mannose-Containing Oligosaccharides with Acetobromo Sugars as the Donors and Partially Protected Mannose Derivatives as the Acceptors via Sugar Orthoester Intermediates
  作者：Wei Wang、Fanzuo Kong

  DOI：10.1002/(sici)1521-3773(19990503)38:9<1247::aid-anie1247>3.0.co;2-j

  日期：1999.5.3

  An orthoester formation/rearrangement sequence, in which 1,2-O-ethylidenated mannose or partially protected mannosides function as the glycosyl acceptors and simple acetobromo sugars as the glycosyl donors (see reaction scheme), provides an efficient and highly regio- and stereoselective route to mannose-containing 1→6, 1→3, and 3,6-branched oligosaccharides with exclusive 1,2-trans linkage.

  原酸酯形成/重排序列，其中1,2-O-亚乙基化的甘露糖或部分受保护的甘露糖苷充当糖基受体，而简单的乙酰溴糖充当糖基供体（请参见反应方案），提供了高效且高度区域和立体选择性的途径含甘露糖的1→6、1→3和3,6-支链寡糖，并具有独特的1,2-反式连接。
• DNA-Templated Homo- and Heterodimerization of Peptide Nucleic Acid Encoded Oligosaccharides that Mimick the Carbohydrate Epitope of HIV
  作者：Katarzyna Gorska、Kuo-Ting Huang、Olivier Chaloin、Nicolas Winssinger

  DOI：10.1002/anie.200903328

  日期：2009.9.28

  hybridization has been utilized to generate a combinatorial library of structures that emulate the topologies of complex carbohydrates interacting with an antibody that shows broad‐spectrum activity against HIV. This simple method involves attaching oligosaccharides tagged with peptide nucleic acids onto DNA templates in a controlled manner (see schematic picture).

  全部受控制：杂交的可编程性已用于生成结构的组合文库，该文库模拟复杂碳水化合物与抗体相互作用的拓扑结构，该抗体显示出针对HIV的广谱活性。这种简单的方法涉及以受控方式将标记有肽核酸的寡糖附着到DNA模板上（请参见示意图）。
• A facile regio- and stereoselective synthesis of mannose octasaccharide of the N-glycan in human CD2 and mannose hexasaccharide antigenic factor 13b
  作者：Yuliang Zhu、Langqiu Chen、Fanzuo Kong

  DOI：10.1016/s0008-6215(01)00307-x

  日期：2002.2

  A highly concise and effective synthesis of the mannose octasaccharide of the N-linked glycan in the adhesion domain of human CD2 was achieved via TMSOTf-promoted selective 6-glycosylation of a trisaccharide 4,6-diol acceptor with a pentasaccharide donor, followed by deprotection. The pentasaccharide was constructed by selective 3,6-diglycosylation of 1,2-O-ethylidene-beta-D-mannopyranose with 2-O-acetyl-3

  通过TMSOTf促进三糖4,6-二醇受体与五糖供体的选择性6-糖基化，然后脱保护，实现了在人CD2粘附域中N-连接聚糖的甘露糖八糖的高度简洁和有效的合成。 。通过用2-O-乙酰基-3,4,6-三-O-苯甲酰基-α-D-甘露吡喃糖基-对1,2-O-亚乙基-β-D-甘露吡喃糖进行选择性3,6-二糖基化来构建五糖。 （1-> 2）-3,4,6-三-O-苯甲酰基-α-D-甘露吡喃糖基三氯乙酰亚胺酸酯，而三糖是通过烯丙基4,6-O-亚苄基-α的选择性3-O-糖基化获得的-D-甘露吡喃糖苷与相同的二糖三氯乙酰亚胺酸酯，然后进行脱苄基作用。甘露糖六糖抗原因子13b是通过三糖供体2-O-乙酰-3,4，
• Highly Efficient Synthesis of the Mannose Nonasaccharide of the N-Glycan Expressed on the HIV Glycoprotein gp 120
  作者：Yuliang Zhu、Fanzuo Kong

  DOI：10.1055/s-2001-16062

  日期：——

  A highly concise and effective synthesis of the mannose nonasaccharide of the glycan expressed on the HIV protein gp 120 was achieved via TMSOTf promoted selective 6-glycosylation of a tetrasaccharide 4,6-diol acceptor with a pentasaccharide donor followed by deprotection. The pentasaccharide was constructed by selective 3,6-diglycosylation of 1,2-O-ethylidene-β-d-mannopyranose with 2-O-acetyl-3,4,6-tri-O-benzoyl-α-d-mannopyranosyl-(1 → 2)-3,4,6-O-benzoyl-α-d-mannopyranosyl trichloroimidate while the tetrasaccharide was obtained by selective 3-O-glycosylation of allyl 4,6-O-benzilidene-α-d-mannopyranoside with 2,3,4,6-tetra-O-benzoyl-α-d-mannopyranosyl-(1 → 2)-3,4,6-tri-O-benzoyl-α-d-mannopyranosyl-(1 → 2)-3,4,6-tri-O-benzoyl-α-d-mannopyranosyl trichloroimidate.

  通过 TMSOTf 促进四糖-4,6-二醇受体与五糖供体的选择性 6-糖基化，然后进行脱保护，实现了表达在 HIV 蛋白 gp 120 上的甘露糖非异构体的高效简洁合成。五糖是通过 1,2-O-ethylidene-β-d-mannopyranose 与 2-O-acetyl-3,4,6-tri-O-benzoyl-α-d-mannopyranosyl-(1 → 2)-3,4,6-O-benzoyl-α-d-mannopyranosyl trichloroimidate 的选择性 3,6-二糖基化构建的，而四糖则是通过烯丙基 4,6-O-benzilidene-β-d-mannopyranose-(1 → 2)-3,4,6-O-benzoyl-α-d-mannopyranosyl trichloroimidate 的选择性 3-O-糖基化获得的、6-O-二苯甲酰基-δ-d-吡喃甘露糖苷与 2,3,4,6-四-O-苯甲酰基-δ-d-吡喃甘露糖基-(1→2)-3,4,6-三-O-苯甲酰基-δ-d-吡喃甘露糖基-(1→2)-3,4,6-三-O-苯甲酰基-δ-d-吡喃甘露糖基三氯亚氨酸酯进行选择性 3-O-糖基化反应得到四糖。
• Highly Regio- and Stereoselective Synthesis of Bioactive Oligosaccharides Using 1,2-<i>O</i>-Ethylidene-α-<scp>d</scp>-gluco- and -β-<scp>d</scp>-Mannopyranose as the Acceptors and Acetobromosugars as the Donors via Ortho Ester Intermediates
  作者：Wei Wang、Fanzuo Kong

  DOI：10.1021/jo982508e

  日期：1999.7.1

  This paper presents a new, and effective method for highly regio- and stereoselective synthesis of oligosaccharides with 1,2-trans linkages using 1,2-O-ethylidenated gluco- and mannopyranose as the acceptors and simple acetobromosugars as the glycosyl donors through ortho ester formation-rearrangement strategy. Biologically important 3,6-branched oligosaccharides such as the phytoalexin elicitor hexasaccharide

  本文提出了一种以 1,2-O-亚乙基化葡萄糖和吡喃甘露糖为受体，以简单的乙酰溴糖为糖基供体通过原酸酯高度区域选择性和立体选择性合成具有 1,2-反式键的寡糖的新方法。形成重排策略。生物学上重要的 3,6-支链寡糖，如植物抗毒素诱导剂六糖和结合 ConA 的 3,6-支链甘露三糖很容易通过新方法以高产率合成。