1,3,4,6-tetra-O-benzyl-α,β-D-fructofuranose | 28697-72-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,4,6-tetra-O-benzyl-α,β-D-fructofuranose
• 英文别名: 1,3,4,6-tetra-O-benzyl-D-fructofuranose；(3S,4R,5R)-3,4-bis(phenylmethoxy)-2,5-bis(phenylmethoxymethyl)oxolan-2-ol
• CAS: 28697-72-5
• 化学式: C₃₄H₃₆O₆
• 分子量: 540.656
• InChiKey: LQAPNUOZMVWFMX-HBQPKYPGSA-N

物化性质

• 沸点：
  672.7±55.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  40
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,3,4,6-tetra-O-benzyl-α,β-D-fructofuranose 在 钯 三苄胺 、 氢气 、 sodium methylate 、 silver perchlorate 作用下， 以 甲醇 、 水 、 溶剂黄146 、 苯 为溶剂， 反应 24.0h， 生成 β-D-fructofuranosyl-(2->1)-2-acetamido-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of 2-amino-2-deoxy-α-d-glucopyranosyl β-d-fructofuranoside (2-amino-2-deoxysucrose) via Koenigs-Knorr reaction

  摘要：

  DOI：

  10.1016/0008-6215(82)84045-7
• 作为产物：
  描述：

  1,3,4,6-tetra-O-benzyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 在 三氟甲磺酸 作用下， 生成 1,3,4,6-tetra-O-benzyl-α,β-D-fructofuranose
  参考文献：
  名称：

  Pavia, Andre A.; Ung-Chhun, Sak N., Canadian Journal of Chemistry, 1981, vol. 59, p. 482 - 490

  摘要：

  DOI：

文献信息

• Preparation of partially benzylated mono-, di-, and trisaccharides by selective cleavage of the β-fructofuranosidic linkage in fully benzylated sucrose and sucrose-related oligosaccharides under acidic conditions
  作者：Takashi Yamanoi、Noriko Misawa、Sho Matsuda、Mikio Watanabe

  DOI：10.1016/j.carres.2008.03.024

  日期：2008.6

  Several partially benzylated mono-, di-, and trisaccharides having an anomeric hydroxyl group were successfully prepared by selective cleavage of the beta-fructofuranosidic linkage in fully benzylated sucrose and sucrose-related oligosaccharides derived from lactosucrose, raffinose, melezitose, stachyose, and nystose under acidic conditions using 1:10 75% aqueous sulfuric acid-dioxane at room temperature

  通过选择性地在完全苄基化的蔗糖和衍生自乳糖蔗糖，棉子糖，松三糖，水苏糖和核糖的蔗糖相关的低聚糖中，β-果糖呋喃糖苷键的选择性裂解，成功制备了具有异头羟基的部分部分苄基化的单糖，二糖和三糖在酸性条件下，使用1:10 75％硫酸-二恶烷水溶液在室温下放置1h。
• 1,3,4,6-tetra-O-benzyl-d-fructofuranose and some of its derivatives
  作者：Robert K. Ness、Harry W. Diehl、Hewitt G. Fletcher

  DOI：10.1016/s0008-6215(00)84891-0

  日期：1970.4

  -fructofuranose derivative has been further characterized through the preparation of a p -nitrobenzoate, a p -phenylazobenzoate and a benzoate — all crystalline derivatives. To confirm the structure of 4 , it was also made through the hydrolysis of octa- O -benzylsucrose and by the partial oxidation of 1,3,4,6-tetra- O -benzyl- d -mannitol ( 11 ); the preparation of 11 and of two crystalline derivatives therefrom

  摘要通过以下步骤，由d-果糖获得了晶体1,3,4,6-四-O-苄基-d-果糖呋喃糖（4），总收率为60％。 d-果糖呋喃糖苷→4。通过制备对-硝基苯甲酸酯，对-苯偶氮苯甲酸酯和苯甲酸酯（均为结晶衍生物），进一步表征了新的d-果糖呋喃糖衍生物。为了证实4的结构，它还通过八-O-苄基蔗糖的水解和1,3,4,6-四-O-苄基-d-甘露糖醇的部分氧化制得（11）。描述了由其制备11和两种结晶衍生物的方法。
• SYNTHESIS OF 2-AMINO-2-DEOXY-α-D-GLUCOPYRANOSYL β-D-FRUCTOFURANOSIDE (2-AMINO-2-DEOXY-SUCROSE
  作者：Shinkiti Koto、Shigeru Inada、Shonosuke Zen

  DOI：10.1246/cl.1980.183

  日期：1980.2.5

  2-Amino-2-deoxy-α-d-glucopyranosyl β-d-fructofuranoside (2-amino-2-deoxy-sucrose) was synthesized by condensation of 3,4,6-tri-O-acetyl-2-(2,4-dinitroanilino)-2-deoxy-α-d-glucopyranosyl bromide and 1,3,4,6-tetra-O-benzyl-d-fructofuranose with the aid of silver perchlorate and tribenzylamine in benzene, followed by removal of protecting groups.

  2-氨基-2-脱氧-α-d-吡喃葡萄糖基β-d-呋喃果糖苷（2-氨基-2-脱氧-蔗糖）通过3,4,6-三-O-乙酰基-2-(2 ,4-二硝基苯胺基)-2-脱氧-α-d-吡喃葡萄糖基溴和1,3,4,6-四-O-苄基-d-呋喃果糖在高氯酸银和三苯胺的苯溶液中反应，然后除去保护层组。
• Synthesis of 1-thiosucrose and anomers, and the behavior of levansucrase and invertase with this substrate analog
  作者：Jacques Defaye、Hugues Driguez、Sabine Poncet、Régis Chambert、Marie-Françoise Petit-Glatron

  DOI：10.1016/0008-6215(84)85287-8

  日期：1984.7

  6-tetra- O -acetyl-1-thio-α- d -glucopyranose and 1,3,4,6-tetra- O -benzyl- d -fructofuranose in dichloromethane, followed by a l.c. separation of the deprotected resulting disaccharides, led to 1-thiosucrose (β- d -fructofuranosyl 1-thio-α- d -glucopyranoside), and α- d -fructofuranosyl 1-thio-α- d -glucopyranoside, in respective 15 and 22% overall yields. Similarly, 2,3,4,6-tetra- O -acetyl-1-thio-β-

  摘要Lewis酸催化2,3,4,6-四-O-乙酰基-1-硫代-α-d-吡喃葡萄糖与1,3,4,6-四-O-苄基-d-呋喃呋喃糖之间的缩合反应。二氯甲烷，然后LC分离脱保护的所得二糖，生成1-硫代蔗糖（β-d-果呋喃糖基1-硫代-α-d-吡喃葡萄糖苷）和α-d-果糖呋喃糖基1-硫代-α-d-葡糖吡喃糖苷，分别占总收益的15％和22％。类似地，2,3,4,6-四-O-乙酰基-1-硫代-β-d-吡喃葡萄糖与1,3,4,6-四-O-苄基-d-果糖呋喃糖反应，得到1以6：6的比例，将α-d-果呋喃糖基1-硫代-β-d-吡喃葡萄糖苷（1-硫代异蔗糖）及其β，β-异头物分离为它们的O-乙酰基衍生物。1-硫代蔗糖是枯草芽孢杆菌中蔗糖酶生物合成的诱导剂。
• Synthesis of Kojitriose using Silicon-Tethered Glycosidation.
  作者：Mikael Bols、Christian Orrenius、Niklas Öhrner、C. Rikard Unelius、Karl Hult、Torbjörn Norin、Muhammed Nour Homsi、Frank K. H. Kuske、Monika Haugg、Nathalie Trabesinger-Rüf、Elmar G. Weinhold

  DOI：10.3891/acta.chem.scand.50-0931

  日期：——

  Reaction of 3,4,6-tri-O-acetyl-beta-D-glucopyranosyl chloride (1) with potassium phenylselenate gave phenyl 3,4,6-tri-O-acetyl-1-seleno-alpha,beta-D-glucopyranoside (2) in 59% yield. Silylation of benzyl 3,4,6-tri-O-benzyl-beta-D-glucopyranoside (4) with ethyl 3,4,6-tri-O-benzyl-2-O-chlorodimethylsilyl-1-thio-beta-D-glucopyranoside gave benzyl 2-O-(3,4,6-tri-O-benzyl-1-S-ethyl-1-thio-beta-D-glucopyranos-2-O-yldimethylsilyl)-3,4,6-tri-O-benzyl-beta-D-glucopyranoside (5) in 35% yield. Reaction of 5 with N-iodosuccinimide in nitromethane gave benzyl 2-O-(3,4,6-tri-O-benzyl-alpha-D-glucopyranosyl)-3,4,6-tri-O-benzyl-beta-D-glucopyranoside (6) in 45% yield. Chlorodimethylsilylation of phenyl 3,4,6-tri-O-acetyl-1-seleno-alpha-D-glucopyranoside (2 alpha) and reaction with 6 gave benzyl 2-O-[2-O-(3,4,6-tri-O-acetyl-1-Se-phenyl-1-seleno-alpha-D-glucopyranos-2-O-yldimethylsilyl) -3,4,6-tri-O-benzyl-alpha-D-glucopyranosyl]-3,4,6-tri-O-benzyl-beta-D-glucopyranoside (7) in 82% yield. Intramolecular glycosidation of 7 using N-iodosuccinimide in nitromethane gave benzyl 2-O-[2-O-(3,4,6-tri-O-acetyl-alpha-D-glucopyranosyl)-3,4,6-tri-O-benzyl-alpha-D-glucopyranosyl]-3,4,6-tri-O-benzyl-beta-D-glucopyranoside (8) in 45% yield. Deprotection of 8 gave kojitriose (9) in quantitative yield. Chlorodimethylsilylation of 1,3,4,6-tetra-O-benzyl-alpha,beta-D-fructofuranose (10) with dimethyldichlorosilane and pyridine followed by reaction with ethyl 3,4,6-tri-O-benzyl-1-thio-beta-D-glucopyranoside (3) gave ethyl 2-O-(1,3,4,6-tetra-O-benzyl- alpha,beta-D-fructofuranosyloxydimethylsilyl)-3,4,6-tri-O-benzyl-1-thio-beta-D-glucopyranoside (11) in 85% yield. Chlorodimethylsilylation of 1,3,4,6-tetra-O-benzoyl-alpha-D-fructofuranose (12) with dimethyldichlorosilane and triethylamine followed by reaction with phenyl 3,4,6-tri-O-acetyl-1-thio-alpha-D-glucopyranoside (13) gave phenyl 2-O-(1,3,4,6-tetra-O-benzoyl-alpha-D-fructofuranosyloxydimethylsilyl)-3,4,6-tri-O-acetyl-1-thio-alpha-D-glucopyranoside (14) in 62% yield. Both 11 and 14 failed to undergo intramolecular glycosidation.