methyl 2,3,6-tri-O-benzyl-4-C-(carboxymethyl)-4-deoxy-α-D-glucopyranoside | 224324-88-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2,3,6-tri-O-benzyl-4-C-(carboxymethyl)-4-deoxy-α-D-glucopyranoside
• 英文别名: methyl (4S)-2,3,6-tri-O-benzyl-4-deoxy-4-(2-ethanoic acid)-α-D-glucopyranoside；2-[(2S,3R,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]acetic acid
• CAS: 224324-88-3
• 化学式: C₃₀H₃₄O₇
• 分子量: 506.596
• InChiKey: LHHCMEKPGBDOKW-YJEGYNBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  甲基2,3,6-三-O-乙酰基吡喃己糖苷	methyl 2,3,6-tri-O-acetyl-α-D-glucopyranoside	18031-51-1	C13H20O9	320.296

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(2S,3S,4R,5R,6R)-2-[[(2S,3R,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]methyl]-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol	365418-10-6	C56H62O10	895.102
  ——	methyl (4S)-2,3,6-tri-O-benzyl-4-deoxy-4-C-((3,4,6-tri-O-benzyl-1,2-dideoxy-D-arabino-hex-1-enyl)-(2-ethanoate))-α-D-glucopyranoside	365418-07-1	C57H62O10	907.113
  ——	methyl (4S)-2,3,6-tri-O-benzyl-4-deoxy-4-C-((3,4,6-tri-O-benzyl-1,2-dideoxy-D-arabino-hex-1-enyl)-2-propene)-α-D-glucopyranoside	365418-08-2	C58H64O9	905.141
  ——	Methyl 4-C-(2,6-anhydro-1-deoxy-D-glycero-D-gulo-heptit-1-yl)-4-deoxy-α-D-glucopyranoside	107032-98-4	C14H26O10	354.354
  ——	methyl 4-C-(2,6-anhydro-7-O-tert-butyl(diphenyl)silyl-4,5-O-isopropylidene-1-deoxy-D-glycero-D-manno-heptitol-1-C-yl)-2,3,6-tri-O-benzyl-4-deoxy-α-D-glucopyranoside	652991-32-7	C54H66O10Si	903.198

反应信息

• 作为反应物：
  描述：

  methyl 2,3,6-tri-O-benzyl-4-C-(carboxymethyl)-4-deoxy-α-D-glucopyranoside 在 palladium on activated charcoal 、 bis[1,1-di(trifluoromethyl)ethoxy][(2,6-diisopropylphenyl)imino](2-methyl-2-phenylpropylidene)molybdenum 、 lead(II) chloride 4-二甲氨基吡啶 、 四甲基乙二胺 、 氢气 、 四氯化钛 、 N,N'-二环己基碳二亚胺 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 60.0 ℃ 、344.74 kPa 条件下， 反应 30.0h， 生成 Methyl 4-C-(2,6-anhydro-1-deoxy-D-glycero-D-gulo-heptit-1-yl)-4-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and Partial Biological Evaluation of a Small Library of Differentially-Linked β-C-Disaccharides¹

  摘要：

  The synthesis of a small library of differentially-linked beta-C-disaccharides has been carried out through the use of a radical allylation-RCM strategy. Acids 6 were prepared by Keck allylation of a suitable carbohydrate-based radical precursor, followed by oxidative cleavage of the formed alkene. Dehydrative coupling of these acids with the known olefin alcohol 5 then gave the precursor esters 7 in excellent yield. Methylenation of the esters 7 was followed by RCM and in situ hydroboration-oxidation of the formed glycals to furnish the protected beta-C-disaccharides 10 in good overall yield. Five examples were then deprotected and screened for their efficacy as enzyme inhibitors of beta-glycosidase and against several solid-tumor cell lines for in vitro differential cytotoxicity.

  DOI：

  10.1021/jo030039x
• 作为产物：
  描述：

  甲基2,3,6-三-O-乙酰基吡喃己糖苷 在 咪唑 、 sodium chlorite 、 sodium periodate 、 potassium dihydrogenphosphate 、 四氧化锇 、 2-甲基-2-丁烯 、 偶氮二异丁腈 、 碘 、 sodium methylate 、 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 叔丁醇 为溶剂， 反应 43.0h， 生成 methyl 2,3,6-tri-O-benzyl-4-C-(carboxymethyl)-4-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  通过闭环复分解来差异连接β-C-二糖的统一方法。

  摘要：

  DOI：

  10.1021/ja010641+

文献信息

• Synthesis of the C‐Glycoside of Methyl α‐<scp>d</scp>‐Altropyranosyl‐(1→4)‐α‐<scp>d</scp>‐glucopyranoside
  作者：Richard W. Denton、David R. Mootoo

  DOI：10.1081/car-120026467

  日期：2003.12.31

  α‐d‐altropyranosyl‐(1→4)‐α‐d‐glucopyranoside 2 was prepared in a convergent fashion, from readily available precursors, 4‐O‐tert‐butyldiphenylsilyl‐1,2‐O‐isopropylidene‐d‐erythro‐S‐phenyl monothiohemiacetal 13 (five steps from D‐ribose) and the known acid, methyl 2,3,6‐tri‐O‐benzyl‐4‐C‐(carboxymethyl)‐4‐deoxy‐α‐d‐glucopyranoside 17 (seven steps from methyl α‐d‐glucopyranoside). The key reactions in

  甲基α-d-四环吡喃糖基-（1→4）-α-d-吡喃吡喃糖苷2的C-糖苷由容易获得的前体4-O-叔丁基二苯基甲硅烷基1,2-O-异亚丙基-d-赤型-S-苯基单硫代半缩醛13（从D-核糖起五个步骤）和已知的酸2,3,6-tri-O-苄基-4-C-（羧甲基）-4-脱氧α -d-吡喃葡萄糖苷17（距甲基α-d-吡喃葡萄糖苷七个步骤）。合成中的关键反应是将硫代乙缩醛-烯醇醚19的氧碳鎓离子环化为C1取代的糖基20，以及将20的立体选择性氢硼化为α-C-altroside21。他70岁生日之际。
• 1-Thio-1,2-<i>O</i>-isopropylidene Acetals:  Novel Precursors for the Synthesis of Complex <i>C</i>-Glycosides
  作者：Noshena Khan、Xuhong Cheng、David R. Mootoo

  DOI：10.1021/ja9843270

  日期：1999.5.1
• A Unified Approach to Differentially Linked β-<i>C</i>-Disaccharides by Ring-Closing Metathesis
  作者：Lei Liu、Maarten H. D. Postema

  DOI：10.1021/ja010641+

  日期：2001.9.1
• Synthesis and Partial Biological Evaluation of a Small Library of Differentially-Linked β-<i>C</i>-Disaccharides¹
  作者：Maarten H. D. Postema、Jared L. Piper、Lei Liu、Jie Shen、Marcus Faust、Peter Andreana

  DOI：10.1021/jo030039x

  日期：2003.6.1

  The synthesis of a small library of differentially-linked beta-C-disaccharides has been carried out through the use of a radical allylation-RCM strategy. Acids 6 were prepared by Keck allylation of a suitable carbohydrate-based radical precursor, followed by oxidative cleavage of the formed alkene. Dehydrative coupling of these acids with the known olefin alcohol 5 then gave the precursor esters 7 in excellent yield. Methylenation of the esters 7 was followed by RCM and in situ hydroboration-oxidation of the formed glycals to furnish the protected beta-C-disaccharides 10 in good overall yield. Five examples were then deprotected and screened for their efficacy as enzyme inhibitors of beta-glycosidase and against several solid-tumor cell lines for in vitro differential cytotoxicity.