(3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside | 79384-19-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside
• 英文别名: 1,2:3,4-di-O-isopropylidene-6-O-(3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-α-D-galactopyranoside；1,2:3,4-di-O-isopropylidene-6-O-(3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranosyl)-α-D-galactopyranose；(1S,2R,6R,8R,9S)-8-[[(2S,4R,5S,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxymethyl]-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecane
• CAS: 79384-19-3
• 化学式: C₃₉H₄₈O₁₀
• 分子量: 676.804
• InChiKey: TWFSCQZMGKLJLJ-JWOCLCCXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  49
• 可旋转键数：
  13
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  92.3
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  3,4,6-三-氧-苄基-2-脱氧-D-吡喃葡萄糖 在 4 A molecular sieve 、 lithium perchlorate 、 cesium fluoride 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 (3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside
  参考文献：
  名称：

  Schene, Heidrun; Waldmann, Herbert, Chemical Communications, 1998, # 24, p. 2759 - 2760

  摘要：

  DOI：

文献信息

• TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals
  作者：Mei-Yuan Hsu、Yi-Pei Liu、Sarah Lam、Su-Ching Lin、Cheng-Chung Wang

  DOI：10.3762/bjoc.12.164

  日期：——

  The thio-additions of glycals were efficiently promoted by a stoichiometric amount of trimethylsilyl bromide (TMSBr) to produce S-2-deoxyglycosides under solvent-free conditions in good to excellent yields. In addition, with triphenylphosphine oxide as an additive, the TMSBr-mediated direct glycosylations of glycals with a large range of alcohols were highly α-selective.

  甘露糖醛酸盐的硫加成反应可以在无溶剂条件下高效地通过等物量的溴化三甲基硅(TMSBr)催化产生良好至优异收率的S-2-脱氧糖苷。此外，加入三苯基膦氧化物作为添加剂，TMSBr介导的甘露糖醛酸盐与多种醇类的直接糖基化反应具有高度α-选择性。
• Stereoselective organocatalyzed glycosylations – thiouracil, thioureas and monothiophthalimide act as Brønsted acid catalysts at low loadings
  作者：G. A. Bradshaw、A. C. Colgan、N. P. Allen、I. Pongener、M. B. Boland、Y. Ortin、E. M. McGarrigle

  DOI：10.1039/c8sc02788a

  日期：——

  Thiouracil catalyzes stereoselective glycosylations with galactals in loadings as low as 0.1 mol%.

  硫尿嘧啶在载体负载量低至0.1 mol％时，催化与半乳糖醛糖苷的立体选择性糖基化。
• Additive‐Free Gold(III)‐Catalyzed Stereoselective Synthesis of 2‐Deoxyglycosides Using Phenylpropiolate Glycosides as Donors
  作者：Mukta Shaw、Amit Kumar

  DOI：10.1002/asia.201900888

  日期：2019.12.13

  Stereoselective synthesis of deoxyglycosides has been achieved from benchtop stable and easily synthesizable deoxy-phenylpropiolate glycosides (D-PPGs) using gold(III) salt as catalyst under external additive-free conditions. Under a simple catalytic system, D-PPGs reacted with a variety of sugar and non-sugar acceptors to produce majorly α-stereoselective O/N-deoxyglycosides in good to excellent yields

  在无外部添加剂的条件下，使用金（III）盐作为催化剂，可从台式稳定且易于合成的脱氧苯丙酸丙二醇酯（D-PPGs）中实现脱氧糖苷的立体选择性合成。在简单的催化系统下，D-PPG与多种糖和非糖受体反应，以高至优异的收率产生主要的α-立体选择性O / N-脱氧糖苷，并再生易于分离和重用的苯丙酸。在优化的反应条件下，含有武装和解除武装团体的脱氧PPG能够很好地存活。另外，展示了D-PPG的正交性质，并且还合成了1，1'-连接的海藻糖型糖。
• Stereoselective Synthesis of 2‐Deoxyglycosides from Glycals by Visible‐Light‐Induced Photoacid Catalysis
  作者：Gaoyuan Zhao、Ting Wang

  DOI：10.1002/anie.201800909

  日期：2018.5.22

  The direct, photoacid‐catalyzed synthesis of 2‐deoxyglycosides from glycals is reported. A series of phenol‐conjugated acridinium‐based organic photoacids were rationally designed, synthesized, and studied alongside the commercially available phenolic catalyst eosin Y. In the presence of such a photoacid catalyst and light, synthetic glycals were activated and coupled with a range of alcohols to afford

  据报道，由糖类直接，光酸催化合成了2-脱氧糖苷。与市售的酚催化剂曙红Y一起，合理设计，合成和研究了一系列基于酚共轭啶基的有机光酸。在这种光酸催化剂和光的存在下，合成糖被活化并与多种醇偶联以高收率和优异的α-选择性提供2-脱氧糖苷。
• Highly stereoselective synthesis of 2-deoxy-α- glycosides and α-disaccharides
  作者：Halszka Bielawska、Maria Michalska

  DOI：10.1016/s0040-4039(98)02167-4

  日期：1998.12

  Highly stereoselective synthesis of 2-deoxy-α-glycosides including disaccharides is described, using S-(2-deoxyglycosyl)phosphorodithioates as glycosyl donors, in the presence of silver perchlorate in acetonitrile

  描述了使用S-（2-脱氧糖基）磷酸二硫代酯作为糖基供体，在乙腈中存在高氯酸银的情况下，高度立体选择性地合成包括二糖在内的2-脱氧-α-糖苷。