1,2:5,6-di-O-isopropylidene-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1-3)-α-D-glucofuranose | 64694-22-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2:5,6-di-O-isopropylidene-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1-3)-α-D-glucofuranose
• 英文别名: 1,2:5,6-di-O-isopropylidene-3-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-D-glucufuranoside；1,2:5,6-di-O-isopropylidene-3-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-D-glucofuranose；O-(2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)-(1-3)-1,2:5,6-di-O-isopropylidenene-α-D-glucofuranoside；(3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6-[(2S,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 64694-22-0
• 化学式: C₄₆H₅₄O₁₁
• 分子量: 782.928
• InChiKey: OIGCVNUVBSVJER-MBVYOOGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  57
• 可旋转键数：
  16
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2,3,4,6-四苄基-D-吡喃葡萄糖 在 三氟甲磺酸三甲基硅酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 1,2:5,6-di-O-isopropylidene-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1-3)-α-D-glucofuranose
  参考文献：
  名称：

  Dichloro‐cyanoacetimidates as Glycosyl Donors

  摘要：

  Transformation of 1-O-unprotected glucose and galactose derivatives (1a-d) into O-glycosyl dichloro-cyanoacetimidates (2a-d) was performed with dichloro-cyanoacetonitrile in the presence of DBU as base. Reaction with different acceptors (3a-d) under TMSOTf catalysis afforded glycosides 4 in high yields. Competition experiments with O-glucopyranosyl trichloroacetimidate 10a, bearing a 4-tert-butylbenzyl group at 6-O, and O-glucopyranosyl dichloro-cyanoacetimidate 10b, bearing a 4-methylbenzyl group at 6-O, displayed similar reactivities for these two types of glycosyl donors.

  DOI：

  10.1080/07328300701410650

文献信息

• 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。
• A new efficient glycosylation method employing glycosyl pentenoates and PhSeOTf
  作者：Tae Jin Choi、Ju Yuel Baek、Heung Bae Jeon、Kwan Soo Kim

  DOI：10.1016/j.tetlet.2006.10.158

  日期：2006.12

  The PhSeOTf promoted glycosylations of various glycosyl acceptors with mannosyl pentenoates and glucosyl pentenoates as glycosyl donors afforded corresponding disaccharides in high yields. And the present glycosyl pentenoates/PhSeOTf method showed that the complete α-selective mannosylation of secondary alcohol acceptors was achieved with 2,3,4,6-tetra-O-benzyl-d-mannopyranosyl pentenoate to give α-disaccharides

  PhSeOTf以甘露糖基戊烯酸酯和葡糖基戊烯酸酯促进各种糖基受体的糖基化，因为糖基供体以高收率提供了相应的二糖。目前的糖基戊烯酸酯/ PhSeOTf方法表明，用2,3,4,6-四-O-苄基-d-甘露吡喃糖基戊烯酸酯可以实现仲醇受体的完整α-选择性甘露糖基化反应，从而获得高收率的α-二糖。
• Solvent and Other Effects on the Stereoselectivity of Thioglycoside Glycosidations
  作者：Alexei Demchenko、Thomas Stauch、Geert-Jan Boons

  DOI：10.1055/s-1997-5762

  日期：1997.7

   Faculty Selected Works of Alexei Demchenko Curators' Professor of Chemistry and Biochemistry | [e-mail] | 314-5167995 Professor Demchenko received his M. Sc. in Chemical Engineering from the D. I. Mendeleyev University of Chemical Technology of Russia, Moscow (1988) and his Ph. D. in Organic Chemistry from the N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences,

   Alexei Demchenko 策展人化学与生物化学教授选集 | [e-mail] | 314-5167995 Demchenko 教授获得理学硕士学位。在莫斯科的 DI Mendeleyev 化学技术大学获得化学工程博士学位（1988 年），在莫斯科俄罗斯科学院 ND Zelinsky 有机化学研究所获得有机化学博士学位（1993 年）。在 2001 年加入 UMSL 学院之前，他是伯明翰大学（英国）的博士后研究员和佐治亚大学复杂碳水化合物研究中心的研究助理。他被任命为化学和生物化学的策展人教授2014. 阅读更多 
• Glycosylidene Carbenes. Part 6. Synthesis of alkyl and fluoroalkyl glycosides
  作者：Karin Briner、Andrea Vasella

  DOI：10.1002/hlca.19920750218

  日期：1992.3.18

  55% of the imidate 10. Glycosidation of di-O-isopropylideneglucose 15 leads to 16 (CH2Cl2, r.t.; 65%, α-D/ β-D = 33:67). That glycosidation occurs by initial protonation of the intermediate glycosylidene carbene is evidenced, for strongly acidic alcohols, by the formation of 10, derived from the attack of (CF3)2MeCO− on an intermediate nitrilium ion (Scheme 4), and for weakly acidic alcohols, by the

  描述了在热和/或光解条件下，来自二嗪1的糖苷和一系列醇的合成。产率和非对映选择性取决于醇，溶剂和反应温度的p K HA值。室温下，CH 2 Cl 2中的弱酸性醇（MeOH，EtOH，i-PrOH和t - BuOH，各1当量）的糖基化导致糖苷2–5的收率介于60％至34％之间（方案1和表1）。在-70至-60°时，产率明显更高。在CH 2 Cl 2中，非对映选择性非常低。然而，在THF中，在-70至-60°之间，i-PrOH的糖基化导致比率为8:92的α-D-/β-D- 4。酸性更强的醇，例如CF 3 CH 2 OH，（CF 3）2 CHOH和（CF 3）2 C（Me）OH，以及高度氟化的长链醇CF 3（CF 2）5（CH 2）2 OH（11）与CHF 2（CF 2）9 CH 2 OH（13）反应（CH 2 Cl 2，rt）的收率介于73％和85％之间，主要导致β-D-葡萄糖苷β-D- 6至β-D-
• An extremely mild and stereocontrolled construction of 1,2-cis-α-glycosidic linkages via benzyl-protected glycopyranosyl diethyl phosphites
  作者：Hiroko Tanaka、Hiroki Sakamoto、Ai Sano、Seiichi Nakamura、Makoto Nakajima、Shunichi Hashimoto

  DOI：10.1039/a902845e

  日期：——

  A highly stereocontrolled 1,2-cis-α-glycosidation reaction under conditions mild enough for acid-labile alcohols has been developed using benzyl-protected glycopyranosyl diethyl phosphites as glycosyl donors in the presence of 2,6-di-tert-butylpyridinium iodide and tetrabutylammonium iodide.

  在 2,6-二叔丁基吡啶鎓碘化物和四丁基铵碘化物存在下，以苄基保护的吡喃糖基二乙基膦酸盐为糖基供体，开发出了一种高度立体可控的 1,2-顺式-δ-糖苷化反应，其条件温和，足以适用于酸亲和醇。