2,3,4-tri-O-benzyl-α-D-xylopyranosyl fluoride | 95898-05-8

• 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: 2,3,4-tri-O-benzyl-α-D-xylopyranosyl fluoride
• 英文别名: 2,3,4-tris-O-(phenylmethyl)-D-xylopyranosyl fluoride；(2R,3R,4S,5R)-2-fluoro-3,4,5-tris(phenylmethoxy)oxane
• CAS: 95898-05-8
• 化学式: C₂₆H₂₇FO₄
• 分子量: 422.496
• InChiKey: JKQUXRMGCFCCOB-ZJSPYRCASA-N

物化性质

• 沸点：
  528.3±50.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzyl-α-D-xylopyranosyl fluoride 在 三氟甲磺酸三甲基硅酯 、 氨 、 lithium 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.83h， 生成 (2S,3R,4S,5R)-2-{(2S,3R,4S,5S,6R)-2-[(2R,4aR,8aS)-5-(2-Furan-3-yl-ethyl)-1,1,4a,6-tetramethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-2-yloxy]-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yloxy}-tetrahydro-pyran-3,4,5-triol
  参考文献：
  名称：

  Syntheses of sweet tasting diterpene glycosides, baiyunoside and analogs

  摘要：

  Total syntheses of sweet tasting diterpene glycosides, baiyunoside, phlomisosides I and II, as well as a variety of analogs have accomplished by means of 2'-discriminated glycosylation followed by Noyori's glycosylation from racemic baiyunol. Sweet tastes of these synthetic glycosides have evaluated qualitatively.

  DOI：

  10.1016/s0040-4020(01)92246-x
• 作为产物：
  描述：

  1-O-acetyl-2,3,4-tri-O-benzyl-D-xylopyranose 在 氢氟酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以100%的产率得到2,3,4-tri-O-benzyl-α-D-xylopyranosyl fluoride
  参考文献：
  名称：

  使用糖基氟化物和三氟化硼乙醚化物对醇和甲硅烷基醚进行立体选择性糖基化

  摘要：

  使用吡喃糖和呋喃糖系列的O-烷基-，O-酰基和乙缩醛保护的糖基氟化物和CH 2 Cl 2中的三氟化硼醚，可以实现醇及其甲硅烷基醚的立体选择性糖基化。

  DOI：

  10.1002/hlca.19850680134

文献信息

• Synthesis of Glycosyl Fluorides by Photochemical Fluorination with Sulfur(VI) Hexafluoride
  作者：Sungjin Kim、Yaroslav Khomutnyk、Anton Bannykh、Pavel Nagorny

  DOI：10.1021/acs.orglett.0c03915

  日期：2021.1.1

  glycosyl fluorides using sulfur(VI) hexafluoride as an inexpensive and safe fluorinating agent and 4,4′-dimethoxybenzophenone as a readily available organic photocatalyst. This mild method was employed to generate 16 different glycosyl fluorides, including the substrates with acid and base labile functionalities, in yields of 43%–97%, and it was applied in continuous flow to accomplish fluorination on an

  本研究描述了一种使用六氟化硫 (VI) 作为廉价且安全的氟化剂和 4,4'-二甲氧基二苯甲酮作为易于获得的有机光催化剂光催化生成糖基氟的新方法。这种温和的方法用于生成 16 种不同的糖基氟化物，包括具有酸和碱不稳定官能团的底物，产率为 43%–97%，并以连续流方式应用，以 7.7 g 的规模和 93% 的产率完成氟化.
• Synthesis of New Serine-Linked Oligosaccharides in Blood-Clotting Factors VII and IX and Protein Z.The Syntheses of<i>O</i>-α-D-Xylopyranosyl-(1→3)-D-glucopyranose,<i>O</i>-α-D-Xylopyranosyl-(1→3)-<i>O</i>-α-D-xylopyranosyl-(1→3)-D-glucopyranose, and Their Conjugates with Serine
  作者：Koichi Fukase、Sumihiro Hase、Tokuji Ikenaka、Shoichi Kusumoto

  DOI：10.1246/bcsj.65.436

  日期：1992.2

  prepared from 2,3,4-tri-O-benzyl-α-D-xylopyranosyl fluoride and allyl 2,4,6-tri-O-acetyl-α-D-grucopyranoside (9a) using tin(II) chloride and silver perchlorate as glycosylating reagents. The trisaccharide α-D-Xylp(1→3)-α-D-Xylp(1→3)-D-Glcp was prepared from O-(2,3,4-tri-O-benzyl-α-D-xylopyranosyl)-(1→3)-2,4-di-O-benzyl-α,β-D-xylopyranosyl fluoride and 9a with the same reagents. Their conjugates with

  为了阐明它们的生物学功能，合成了最近在牛和人凝血因子 VII、IX 和蛋白 Z 的第一个表皮生长因子样结构域中发现的二糖和三糖序列及其与丝氨酸的结合物。二糖 α-D-Xylp(1→3)-D-Glcp 由 2,3,4-三-O-苄基-α-D-吡喃木糖基氟和烯丙基 2,4,6-三-O-乙酰基制备-α-D-吡喃葡萄糖苷 (9a) 使用氯化锡 (II) 和高氯酸银作为糖基化试剂。三糖 α-D-Xylp(1→3)-α-D-Xylp(1→3)-D-Glcp 由 O-(2,3,4-tri-O-benzyl-α-D-xylopyranosyl )-(1→3)-2,4-二-O-苄基-α,β-D-吡喃木糖基氟和9a用相同的试剂。它们与丝氨酸、α-D-Xylp(1→3)-β-D-Glcp(1→3)-L-Ser 和 α-D-Xylp(1→3)-α-D-Xylp(1→ 3)-β-D-Glcp(1→3)-L-Ser，通过
• Electrochemical Synthesis of Glycosyl Fluorides Using Sulfur(VI) Hexafluoride as the Fluorinating Agent
  作者：Sungjin Kim、Pavel Nagorny

  DOI：10.1021/acs.orglett.2c00431

  日期：2022.4.1

  different glycosyl fluorides in 73–98% yields on up to a 5 g scale that relies on the use of SF6 as an inexpensive and safe fluorinating agent. Cyclic voltammetry and related mechanistic studies carried out subsequently suggest that the active fluorinating species generated through the cathodic reduction of SF6 are transient under these reductive conditions and that the sulfur and fluoride byproducts are

  该手稿描述了 17 种不同糖基氟化物的电化学合成，产量高达 5 g，产量为 73–98%，依赖于使用 SF 6作为廉价且安全的氟化剂。随后进行的循环伏安法和相关机理研究表明，通过 SF 6阴极还原产生的活性氟化物质在这些还原条件下是瞬态的，并且硫和氟化物副产物被 Zn(II) 有效清除以生成良性盐。
• Synthesis of C-pentopyranosylphloroacetophenone derivatives and their anomerization
  作者：Toshihiro Kumazawa、Tomoki Saito、Shigeru Matsuba、Shingo Sato、Jun-ichi Onodera

  DOI：10.1016/s0008-6215(00)00259-7

  日期：2000.12

  A 3-C-beta-D-xylopyranosylphloroacetophenone derivative was synthesized via reaction of 2,3,4-tri-O-benzyl-alpha-D-xylopyranosyl fluoride and 2,4-di-O-benzylphloroacetophenone in the presence of boron trifluoride diethyl etherate. Alternatively, the reaction of 2,3,4-tri-O-benzyl-beta-L-arabinopyranosyl fluoride with 2,4-di-O-benzylphloroacetophenone afforded both the 3-C-alpha-L- and the 3-C-beta

  在三氟化硼的存在下，通过2,3,4-三-O-苄基-α-D-吡喃吡喃二氟与2,4-二-O-苄基苯乙酰苯反应，合成了3-C-β-D-吡喃并吡喃二乙酮衍生物。二乙醚。或者，使2,3,4-三-O-苄基-β-L-阿拉伯吡喃糖基氟与2,4-二-O-苄基氯苯乙酮反应得到3-C-α-L-和3-C- β-L-阿拉伯吡喃并吡喃糖基苯乙酮衍生物在相同的反应条件下。C-β-L-阿拉伯糖苷，热力学产物，是通过反应过程中的动力学产物C-α-L-阿拉伯糖苷的异构化而产生的。该产物混合物的组成显然由1，3-双轴和2，4-双轴相互作用决定。
• Total synthesis of baiyunoside by a novel 2′ discriminated glycosidation
  作者：Hidetoshi Yamada、Mugio Nishizawa

  DOI：10.1016/s0040-4039(00)96495-5

  日期：1987.1