benzyl 2,3,4,6-tetra-O-benzyl-L-glycero-α-D-manno-heptopyranoside | 111570-49-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2,3,4,6-tetra-O-benzyl-L-glycero-α-D-manno-heptopyranoside
• 英文别名: (2S)-2-phenylmethoxy-2-[(2R,3S,4S,5S,6S)-3,4,5,6-tetrakis(phenylmethoxy)oxan-2-yl]ethanol
• CAS: 111570-49-1
• 化学式: C₄₂H₄₄O₇
• 分子量: 660.807
• InChiKey: AIAMVLFKGIXRBM-BXKHDUSTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  49
• 可旋转键数：
  17
• 环数：
  6.0
• 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：

  benzyl 2,3,4,6-tetra-O-benzyl-L-glycero-α-D-manno-heptopyranoside 生成 O-L-glycero-α-D-manno-heptopyranosyl-(1->7)-L-glycero-D-manno-heptopyranose
  参考文献：
  名称：

  The synthesis of the heptose region of the gram-negative bacterial core oligosaccharides

  摘要：

  DOI：

  10.1016/s0040-4039(01)81044-3
• 作为产物：
  描述：

  2,3,4,6,7-Penta-O-acetyl-L-glycero-α-D-manno-heptopyranosylbromid 在 咪唑 、 盐酸 、 sodium methylate 、 silver trifluoromethanesulfonate 、 sodium hydride 、 1,1,3,3-四甲基脲 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 benzyl 2,3,4,6-tetra-O-benzyl-L-glycero-α-D-manno-heptopyranoside
  参考文献：
  名称：

  Novel Synthesis of Disaccharides Containing the 2-Amino-2-deoxy-β-D-glucopyranosyl Unit and L-Glycero-D-Manno- and 7-Deoxy-L-Glycero-D-Galacto-heptopyranoses

  摘要：

  通过三甲基硅基三氟甲磺酸盐促进的供体1,3,4,6-四-O-乙酰基-2-N-烯丙氧基羰基-2-氨基-2-脱氧-β-D-吡喃葡萄糖与适当受体的糖基化反应，实现了免疫相关七吡喃糖二糖的立体控制合成，且收率极高。

  DOI：

  10.1246/cl.2004.696

文献信息

• Chemoenzymatic synthesis of ADP-d-glycero-β-d-manno-heptose and study of the substrate specificity of HldE
  作者：Tiehai Li、Liuqing Wen、Adriel Williams、Baolin Wu、Lei Li、Jingyao Qu、Jeffrey Meisner、Zhongying Xiao、Junqiang Fang、Peng George Wang

  DOI：10.1016/j.bmc.2013.12.019

  日期：2014.2

  An efficient one-pot three enzymes strategy for chemoenzymatic synthesis of ADP-D-glycero-beta-D-mannoheptose (ADP-D, D-heptose) was reported using chemically synthesized D, D-heptose-7-phosphate and the ADP-D, D-heptose biosynthetic enzymes HldE and GmhB. Moreover, the result of investigating substrate specificity of the kinase action of HldE revealed that HldE had highly restricted substrate specificity towards structurally modified heptose-7-phosphate analogs. Published by Elsevier Ltd.
• Synthesis and serological characterization of l-glycero-α-d-manno-heptopyranose-containing di- and tri-saccharides of the non-reducing terminus of the Escherichia coli K-12 LPS core oligosaccharide
  作者：Konstantin V Antonov、Leon V Backinowsky、Barbara Grzeszczyk、Lore Brade、Otto Holst、Aleksander Zamojski

  DOI：10.1016/s0008-6215(98)00292-4

  日期：1998.12

  Synthesis of the title trisaccharide was accomplished by sugar chain extension starting from the non-reducing terminus: coupling of GlcpNAc with LD-Hepp, then adding Glcp-OAll. An alternative route started from the reducing end: coupling of LD-Hepp with Glcp-OAll, then addition of GlcpNAc. In the synthesis of the title disaccharide a modification of the first approach was employed. The allyl glycosides were coupled with cysteamine, activated with thiophosgene and conjugated to bovine serum albumin (BSA). The neoglycoconjugates obtained were used in immunochemical studies of monoclonal and polyclonal antibodies directed against Escherichia coli K-12 lipopolysaccharide. (C) 1998 Elsevier Science Ltd. All rights reserved.
• DZIEWISZEK, KRZYSZTOF;BANASZEK, ANNA;ZAMOJSKI, ALEKSANDER, STUD. NATUR. PROD. CHEM. VOL. 4. STEREOSELEC. SYNTH. (PT C), AMSTERDAM ET+
  作者：DZIEWISZEK, KRZYSZTOF、BANASZEK, ANNA、ZAMOJSKI, ALEKSANDER

  DOI：——

  日期：——
• The synthesis of the heptose region of the gram-negative bacterial core oligosaccharides
  作者：Krzysztof Dziewiszek、Anna Banaszek、Aleksander Zamojski

  DOI：10.1016/s0040-4039(01)81044-3

  日期：1987.1
• Novel Synthesis of Disaccharides Containing the 2-Amino-2-deoxy-β-D-glucopyranosyl Unit and L-<i>Glycero</i>-D-<i>Manno</i>- and 7-Deoxy-L-<i>Glycero</i>-D-<i>Galacto</i>-heptopyranoses
  作者：Patrick Martin、Vincent Lequart、Roméo Cecchelli、Paul Boullanger、Dominique Lafont、Joseph Banoub

  DOI：10.1246/cl.2004.696

  日期：2004.6

  Stereocontrolled syntheses of immunologically relevant heptopyranose disaccharides were achieved in excellent yields by the trimethylsilyl triflate promoted glycosylation of the donor 1,3,4,6-tetra-O-acetyl-2-N-allyloxycarbonyl-2-amino-2-deoxy-β-d-glucopyranose with the adequate acceptors.

  通过三甲基硅基三氟甲磺酸盐促进的供体1,3,4,6-四-O-乙酰基-2-N-烯丙氧基羰基-2-氨基-2-脱氧-β-D-吡喃葡萄糖与适当受体的糖基化反应，实现了免疫相关七吡喃糖二糖的立体控制合成，且收率极高。