6-O-benzyl-1,2-O-isopropylidene-3-O-methyl-α-D-glucofuranose | 51173-25-2

• 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: 6-O-benzyl-1,2-O-isopropylidene-3-O-methyl-α-D-glucofuranose
• 英文别名: O⁶-benzyl-O¹,O²-isopropylidene-O³-methyl-α-D-glucofuranose；O⁶-Benzyl-O¹,O²-isopropyliden-O³-methyl-α-D-glucofuranose；(1R)-1-[(3aR,5R,6S,6aR)-6-methoxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-phenylmethoxyethanol
• CAS: 51173-25-2
• 化学式: C₁₇H₂₄O₆
• 分子量: 324.374
• InChiKey: WVYNVHMYOBILEL-IBEHDNSVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 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：

  6-O-benzyl-1,2-O-isopropylidene-3-O-methyl-α-D-glucofuranose 在 1,4-二氧六环 、 盐酸 、 calcium hydroxide 、 硫酸 、 水 作用下， 生成 O⁵-benzyl-D-erythro-2-deoxy-pentose-dibenzyldithioacetal
  参考文献：
  名称：

  碳水化合物被碱降解。第七部分 5- ø苄基和3：5- ø -亚苄基-2-脱氧d核糖

  摘要：

  DOI：

  10.1039/jr9540003277
• 作为产物：
  描述：

  5,6-anhydro-1,2-O-isopropylidene-α-D-glucofuranose 在 silver(l) oxide 、 苯甲醇 作用下， 生成 6-O-benzyl-1,2-O-isopropylidene-3-O-methyl-α-D-glucofuranose
  参考文献：
  名称：

  碳水化合物被碱降解。第七部分 5- ø苄基和3：5- ø -亚苄基-2-脱氧d核糖

  摘要：

  DOI：

  10.1039/jr9540003277

文献信息

• Synthesis of allyl and benzyl 4-O-(3,6-di-O-methyl-β-d-glucopyranosyl)-2,3-di-O-methyl-α-l-rhamnopyranoside
  作者：Jose R. Mariño-Albernas、Vicente Verez-Bencomo、Leandro Gonzalez、Carlos S. Perez

  DOI：10.1016/0008-6215(87)80099-x

  日期：1987.8

  Abstract Condensation of 2,4-di- O -acetyl-3,6-di- O -methyl-α- d -glucopyranosyl bromide with either allyl or benzyl 2,4-di- O -methyl-α- l -rhamnopyranoside in the presence of mercuric cyanide, followed by O -deacetylation, gave the title oligosaccharides in excellent yields.

  摘要2,4-二-O-乙酰基-3,6-二-O-甲基-α-d-吡喃葡萄糖基溴化物与烯丙基或苄基的2,4-二-O-甲基-α-1-鼠李糖吡喃糖苷缩合。氰化汞的存在，然后进行O-脱乙酰基反应，可以极好的收率得到标题寡糖。
• Enhanced reactivity of secondary hydroxyl groups in the O-alkylation of carbohydrate-related primary-secondaryvic-glycols. Regioselective 2-O-benzylation of 1,3:2,4-di-O-ethylidene-D-glucitol
  作者：E. A. El'perina、M. I. Struchkova、M. I. Serkebaev、E. P. Serebryakov

  DOI：10.1007/bf00704019

  日期：1993.4

  Partial O-alkylation of 1,3:2,4-di-O-ethylidene-D-glucitol (1a), 1,2-O-isopropylidene-3-O-methyl-alpha-D-glucofuranose (1b), and R-(+)-1-O-benzylglycerol (1c) with benzyl chloride in a KOH/DMSO system results in products of monoalkylation at the secondary (4a-c) and at the primary hydroxyl (2a-c) in ratios of over 95:5 (a), -2:1 (b), and -1:1 (c), whereas (+/-)propane-1,2-diol (1d) gives only the product of 1-O-benzylation (2d). A qualitatively similar result is observed upon O-alkylation of diols (la-e) with 2-methoxyethanol tosylate.
• A simple, mild, and regioselective method for the benzylation of carbohydrate derivatives promoted by silver carbonate
  作者：Satish Malik、Vaibhav A. Dixit、Prasad V. Bharatam、K.P. Ravindranathan Kartha

  DOI：10.1016/j.carres.2009.12.012

  日期：2010.3

  A simple, mild, and regioselective method has been developed for the selective benzylation and p-methoxybenzylation of carbohydrate derivatives in high yields using Ag2CO3 as the promoter. Benzylation of base-labile substrates, for which other reported methods are of little use, has been performed in high yields. (C) 2010 Elsevier Ltd. All rights reserved.
• 2-phenyl-1,3-benzodithiolylium trifluoromethanesulfonate: A reagent for the conversion of alcohols into benzyl ethers and benzoates under mild conditions.
  作者：Mauro Mocerino、Robert V. Stick

  DOI：10.1016/s0040-4039(00)89023-1

  日期：——
• MOCERINO, MAURO;STICK, ROBERT V., TETRAHEDRON LETT., 31,(1990) N1, C. 3051-3054
  作者：MOCERINO, MAURO、STICK, ROBERT V.

  DOI：——

  日期：——