n-octyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: n-octyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside
• 英文别名: (2R,3R,4S,5R,6R)-2-octoxy-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• 化学式: C₄₂H₅₂O₆
• 分子量: 652.871
• InChiKey: LFJKORWCRRSQRS-QBLDGPCBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  48
• 可旋转键数：
  21
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

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
  ——	methyl 2,3,4,6-tetra-O-benzyl α-D-glucopyranoside	19488-61-0	C35H38O6	554.683
  甲基 2,3,4,6-O-四苄基-alpha-D-吡喃葡萄糖苷	methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside	17791-37-6	C35H38O6	554.683
  2,3,4,6-四苄基-D-吡喃葡萄糖	2,3,4,6-Tetra-O-benzyl-D-glucopyranose	4132-28-9	C34H36O6	540.656
  2,3,4,6-四-o-苄基-D-吡喃葡萄糖	2,3,4,6-tetra-O-benzyl-D-glucopyranose	6564-72-3	C34H36O6	540.656
  ——	Methoxy-acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester	78890-59-2	C37H40O8	612.72
  ——	2,3,4,6-tetra-O-benzyl-D-glucopyranosyl methoxyacetate	——	C37H40O8	612.72
  2,3,4,6-四-O-苯基-Alpha-D-吡喃葡萄糖基三氯乙酰亚氨酸	2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate	74808-09-6	C36H36Cl3NO6	685.044
  ——	2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl trichloroacetimidate	90357-89-4	C36H36Cl3NO6	685.044
  ——	2,3,4,6-tetra-O-benzyl-D-glucopyranose trichloroacetimidate	132201-75-3	C36H36Cl3NO6	685.044
  ——	2,3,4,6-tetra-O-benzyl-D-glucopyranosyl diethyl phosphite	193953-69-4	C38H45O8P	660.744

反应信息

• 作为产物：
  描述：

  甲基 Β-D-吡喃葡萄糖苷 在 ytterbium trifluoromethanesulfonate 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 n-octyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  A novel glycosylation concept; microwave-assisted acetal-exchange type glycosylations from methyl glycosides as donors

  摘要：

  Efficient microwave-assisted glycosylations from methyl glucopyranosides are described. We have discussed the effects of microwave irradiation on this unique glycoside exchanging reaction from view points such as amount of Lewis acid promoters and acceptors, hydroxyl protecting groups of methyl glucopyranosides donors for reactivity, and neighboring effect. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2005.05.046

文献信息

• A Visible-Light-Promoted <i>O</i> -Glycosylation with a Thioglycoside Donor
  作者：Mark L. Spell、Kristina Deveaux、Caitlin G. Bresnahan、Bradley L. Bernard、William Sheffield、Revati Kumar、Justin R. Ragains

  DOI：10.1002/anie.201601566

  日期：2016.5.23

  Visible‐light irradiation of 4‐p‐methoxyphenyl‐3‐butenylthioglucoside donors in the presence of Umemoto's reagent and alcohol acceptors serves as a mild approach to O‐glycosylation. Visible‐light photocatalysts are not required for activation, and alkyl‐ and arylthioglycosides not bearing the p‐methoxystyrene are inert to these conditions. Experimental and computational evidence for an intervening

  在梅本试剂和醇受体存在下，对4-对-甲氧基苯基-3-丁烯基硫代葡萄糖苷供体的可见光照射是温和的O-糖基化方法。活化不需要可见光光催化剂，不带有对甲氧基苯乙烯的烷基和芳基硫代糖苷对这些条件呈惰性。提供了反应性必需的中间电子供体-受体复合物的实验和计算证据。伯，仲和叔醇受体的产量范围从中等到高。完全的β-选择性可以通过邻群的参与来实现。
• Lanthanoid(III) triflates as new glycosylation catalysts. Selective and efficient activation of 1-O-methoxyacetyl sugars
  作者：Junji Inanaga、Yasuo Yokoyama、Takeshi Hanamoto

  DOI：10.1016/s0040-4039(00)73563-5

  日期：1993.4

  The reactions of 1-O-methoxyacetyl sugars with alcohols or thiols were effectively promoted by a catalytic amount of lanthanoid(III) triflates such as Tb(OTf)3, Ho(OTf)3, Tm(OTf)3, and Yb(OTJ)3 to give the corresponding glycosides in good to excellent yields.

  催化量的镧系元素（III）三氟甲磺酸酯如Tb（OTf）3，Ho（OTf）3，Tm（OTf）3和Yb（OTJ ）有效地促进了1- O-甲氧基乙酰基糖与醇或硫醇的反应）3以良好至极好的产率得到相应的糖苷。
• Tandem Catalysis Strategy for Direct Glycosylation of 1-Hydroxy Sugars. Methoxyacetic Acid as an Effective Catalytic Mediator
  作者：Yasuo Yokoyama、Junji Inanaga、Takeshi Hanamoto、Shoko Suzuki、Hiroshi Furuno、Kosuke Shimizu

  DOI：10.3987/com-08-s(d)74

  日期：——

  1-Hydroxy sugars were dehydratively coupled with a variety of alcohols including thiophenol in the presence of a catalytic amount of ytterbium(III) triflate [Yb(OTf) 3 ] and methoxyacetic acid to give the corresponding glycosides in good to excellent yields, and in some cases, with high stereoselectivities. The reaction proceeds through selective esterification of 1-hydroxy sugars with methoxyacetic

  在催化量的三氟甲磺酸镱 (III) [Yb(OTf) 3 ] 和甲氧基乙酸的存在下，将 1-羟基糖与包括苯硫酚在内的多种醇脱水偶联，得到相应的糖苷，收率良好至极好，并且在在某些情况下，具有高立体选择性。在作为糖基受体的游离醇存在下，该反应通过 1-羟基糖与甲氧基乙酸的选择性酯化进行。讨论了甲氧基乙酸介导的Yb(OTf) 3 串联催化的机理。
• GaCl3-catalyzed activation of alkynyl glycosides for the synthesis of O-glycosides
  作者：Jhillu S. Yadav、Nagendra N. Yadav、Manoj K. Gupta、Nikhil Srivastava、Basi V. Subba Reddy

  DOI：10.1007/s00706-013-1091-7

  日期：2014.3

  AbstractA catalytic amount of GaCl3 (5 mol%) was found to activate alkynyl glycosides effectively under mild reaction conditions to furnish a variety of O-glycosides in good yields with high β-selectivity. Graphical abstract

  摘要发现在适度的反应条件下催化量的GaCl 3（5mol％）有效地活化炔基糖苷，以高产率和高β选择性提供各种O-糖苷。 图形概要
• A Stereoselective One-stage α-Glucosylation with 2,3,4,6-Tetra-<i>O</i>-benzyl-α-D-glucopyranose and a Mixture of Methanesulfonic Acid, Cobalt(II) Bromide, and Tetraethylammonium Perchlorate
  作者：Shinkiti Koto、Naohiko Morishima、Shonosuke Zen

  DOI：10.1246/bcsj.55.1543

  日期：1982.5

  A one-stage procedure for the stereoselective α-glucosylation of alcohol with 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose and a mixture of methanesulfonic acid, cobalt(II) bromide, and tetraethylammonium perchlorate is described. The mechanism of the glucosylation reaction is discussed.

  醇与 2,3,4,6-四-O-苄基-α-D-吡喃葡萄糖和甲磺酸、溴化钴 (II) 和四乙基高氯酸铵的混合物的立体选择性 α-葡萄糖基化的一步程序是描述。讨论了糖基化反应的机理。