methyl 3,4-di-O-benzyl-β-D-glucopyranoside | 676265-67-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,4-di-O-benzyl-β-D-glucopyranoside
• 英文别名: (2R,3R,4R,5R,6R)-6-(hydroxymethyl)-2-methoxy-4,5-bis(phenylmethoxy)oxan-3-ol
• CAS: 676265-67-1
• 化学式: C₂₁H₂₆O₆
• 分子量: 374.434
• InChiKey: VDXOCUMLSFQTRW-PFAUGDHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  甲基磺酰氯 、 methyl 3,4-di-O-benzyl-β-D-glucopyranoside 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以66%的产率得到methyl 3,4-di-O-benzyl-6-O-methanesulfonyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of monodeoxy and mono-O-methyl congeners of methyl β-d-mannopyranosyl-(1→2)-β-d-mannopyranoside for epitope mapping of anti-Candida albicans antibodies

  摘要：

  A panel of six complementary monodeoxy and mono-O-methyl congeners of methyl beta-D-mannopyranosyl-(1 -> 2)-beta-D-mannopyranoside (1) were synthesized by stereoselective glycosylation of monodeoxy and mono-O-methyl monosaccharide acceptors with a 2-O-acetyl-glucosyl trichloroacetimidate donor, followed by a two-step oxidation-reduction sequence at C-2'. The beta-manno configurations of the final deprotected congeners 2-7 were confirmed by measurement of (1)J(C1,H1) heteronuclear and (3)J(1',2') homonuclear coupling constants. These disaccharide derivatives will be used to map the protective epitope recognized by a protective anti-Candida albicans monoclonal antibody C3.1 (IgG3) and to determine its key polar contacts with the binding site. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2009.07.008
• 作为产物：
  描述：

  methyl 3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 在 三氟甲磺酸二丁硼 、 borane tetrahydrofuran 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 以83%的产率得到methyl 3,4-di-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of monodeoxy and mono-O-methyl congeners of methyl β-d-mannopyranosyl-(1→2)-β-d-mannopyranoside for epitope mapping of anti-Candida albicans antibodies

  摘要：

  A panel of six complementary monodeoxy and mono-O-methyl congeners of methyl beta-D-mannopyranosyl-(1 -> 2)-beta-D-mannopyranoside (1) were synthesized by stereoselective glycosylation of monodeoxy and mono-O-methyl monosaccharide acceptors with a 2-O-acetyl-glucosyl trichloroacetimidate donor, followed by a two-step oxidation-reduction sequence at C-2'. The beta-manno configurations of the final deprotected congeners 2-7 were confirmed by measurement of (1)J(C1,H1) heteronuclear and (3)J(1',2') homonuclear coupling constants. These disaccharide derivatives will be used to map the protective epitope recognized by a protective anti-Candida albicans monoclonal antibody C3.1 (IgG3) and to determine its key polar contacts with the binding site. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2009.07.008

文献信息

• Tandem Epoxidation‐Alcoholysis or Epoxidation‐Hydrolysis of Glycals Catalyzed by Titanium(IV) Isopropoxide or Venturello’s Phosphotungstate Complex
  作者：Pieter Levecque、David W. Gammon、Henok Hadgu Kinfe、Pierre Jacobs、Dirk De Vos、Bert Sels

  DOI：10.1002/adsc.200800079

  日期：2008.7.7

  Venturello’s phosphotungstate complex and titanium(IV) isopropoxide [Ti(O-i-Pr)4] were successfully used as catalysts for the epoxidation-alcoholysis of glycals using hydrogen peroxide [H2O2]. Reaction substrates included a range of variously protected glycals and different alcohols were used as solvents. Ti(O-i-Pr)4 was only effective in methanol as solvent, but gave methyl glycosides in high yields

  Venturello的磷钨酸盐络合物和异丙醇钛（IV）[Ti（O- i- Pr）4 ]已成功用作使用过氧化氢[H 2 O 2 ]的环氧乙烷缩合醇解的催化剂。反应底物包括各种受保护的糖基，不同的醇用作溶剂。钛（O- i- Pr）4仅在甲醇作为溶剂中有效，但以高收率和高选择性得到甲基糖苷。事实证明，Ventrollo复合物是一种用途广泛且高效的催化剂。除了在醇类溶剂中进行环氧化-醇解以外，它还显示了在双相条件下的活性，以允许长链醇的糖基化，并且在苄基化的葡糖的立体选择性二羟基化中非常有效。
• Fluorination of 2-hydroxy-hexopyranosides by DAST: towards formyl C-glycofuranosides from equatorial-2-OH methyl hexopyranosides
  作者：Yolanda Vera-Ayoso、Pastora Borrachero、Francisca Cabrera-Escribano、Ana T. Carmona、Manuel Gómez-Guillén

  DOI：10.1016/j.tetasy.2003.11.034

  日期：2004.2

  Reaction of diversely configured and substituted, unbranched methyl D-hexopyranosides with the DAST in dichloromethane or acetonitrile led to normal substitution products and/or rearranged fluoro compounds (ring-contracted 2,5-anhydro-1-fluoro-1-I-methylhexitol derivatives, 2-methoxy-D-hexopyranosyl fluorides, and, for some 3-azido substrates, rearranged 2-azido-3-fluoro-D-hexopyranosides). When the reaction was performed in acetonitrile, the solvent participation as a nucleophile (Ritter reaction) was observed in one case. For a 2,4-unprotected 3-azido substrate, 2,3-dehydration and fluorination at C(4), the latter with epimerization, took place. F-19/H-1 and F-19/C-13 coupling constant values were systematically applied to discriminate between isomeric structures for fluorinated products, and for some, previously described, coming from five 3-branched-chain D- or L-hexopyranosides, thus discarding the previously reported structural assignment. From the synthetic point of view, the most outstanding result was the preparation of 2,5-anhydro-1-fluoro-1-O-methylhexitols, showing a latent formyl group functionality, a transformation, which was achieved in one case. A rationalization for the formation of the different types of product is also proposed. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis of monodeoxy and mono-O-methyl congeners of methyl β-d-mannopyranosyl-(1→2)-β-d-mannopyranoside for epitope mapping of anti-Candida albicans antibodies
  作者：Corwin M. Nycholat、David R. Bundle

  DOI：10.1016/j.carres.2008.12.011

  日期：2009.3

  A panel of six complementary monodeoxy and mono-O-methyl congeners of methyl beta-D-mannopyranosyl-(1 -> 2)-beta-D-mannopyranoside (1) were synthesized by stereoselective glycosylation of monodeoxy and mono-O-methyl monosaccharide acceptors with a 2-O-acetyl-glucosyl trichloroacetimidate donor, followed by a two-step oxidation-reduction sequence at C-2'. The beta-manno configuration of the final deprotected congeners 2-7 was confirmed by measurement of (1)J(C1.H1) heteronuclear and (3)J(1'.2), homonuclear coupling constants. These disaccharide derivatives will be used to map the epitope recognized bit a protective anti-Candida albicans monoclonal antibody C3.1 (IgG3) and to determine its key polar contacts with the binding site. (C) 2009 Elsevier Ltd. All rights reserved.