1,2-O-isopropylidene-6-O-benzylhexane-1,2,6-triol | 186091-03-2

• 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: 1,2-O-isopropylidene-6-O-benzylhexane-1,2,6-triol
• 英文别名: 2,2-Dimethyl-4-(4-phenylmethoxybutyl)-1,3-dioxolane
• CAS: 186091-03-2
• 化学式: C₁₆H₂₄O₃
• 分子量: 264.365
• InChiKey: WKDZKQRPCVQTHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropylidene-6-O-benzylhexane-1,2,6-triol 在 4-二甲氨基吡啶 、 氨 、 碘 、 三乙胺 、 pyridinium chlorochromate 、 hydroxylamine-O-sulfonic acid 作用下， 以 吡啶 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 148.33h， 生成 [3-(4-Benzyloxy-butyl)-3H-diazirin-3-yl]-methanol
  参考文献：
  名称：

  Synthesis and application of α-?-mannosyl clusters as photoaffinity ligands for mannose-binding proteins: Concanavalin A as a model receptor

  摘要：

  DOI：

  10.1016/s0008-6215(96)00207-8
• 作为产物：
  描述：

  在 氢氧化钾 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 1,2-O-isopropylidene-6-O-benzylhexane-1,2,6-triol
  参考文献：
  名称：

  Syntheses of spacer-armed carbohydrate model compounds

  摘要：

  Commercially available chemicals, such as diethylene glycol, 1,9-nonanediol, 9-decen-1-ol, 1,2,6-hexanetriol, and p-nitrophenol were used to prepare spacer-armed carbohydrate derivatives. Glycosides of D-glucose, N-acetyl-D-glucosamine and 3-O-methyl-D-glucose have been synthesized, carrying reactive groups at the end of the spacer-arms. These glycosides are capable of forming neoglycoproteins. When bromo sugars were reacted with highly apolar aglycones in the presence of mercuric cyanide or mercuric bromide, a considerable amount of '2-OH-compounds' (such as 9-hydroxynonyl 3,4,6-tri-O-acetyl-beta-D-glucopyranoside) were formed. Some spacer-armed derivatives (such as 9,10-epoxydecyl beta-D-glucopyranoside) are theoretically a mixture of diastereomers, but this fact does not mirror in the H-1 and C-13 NMR spectra. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00256-x

文献信息

• MW-assisted Er(OTf)3-catalyzed mild cleavage of isopropylidene acetals in Tricky substrates
  作者：Antonio Procopio、Marco Gaspari、Monica Nardi、Manuela Oliverio、Roberto Romeo

  DOI：10.1016/j.tetlet.2008.01.089

  日期：2008.3

  Erbium(III) trifluoromethane sulfonate is proposed as a very gentle Lewis acid catalyst in a MW-assisted chemoselective method for the cleavage of isopropylidene acetals in awkward substrates by using pure water as the solvent.

  提出了一种三氟甲烷磺酸is（III），它是一种MW辅助化学选择方法中非常温和的路易斯酸催化剂，用于通过使用纯水作为溶剂裂解难处理的底物中的异亚丙基缩醛。
• Direct Synthesis of Free α-Amino Acids by Telescoping Three-Step Process from 1,2-Diols
  作者：Haruki Inada、Masatoshi Shibuya、Yoshihiko Yamamoto

  DOI：10.1021/acs.orglett.8b03910

  日期：2019.2.1

  of α-amino acids from the corresponding 1,2-diols has been developed. This process enables the direct synthesis of free α-amino acids without any protection/deprotection step. This method was also effective for the preparation of a 15N-labeled α-amino acid. 1,2-Diols bearing α,β-unsaturated ester moieties afforded bicyclic α-amino acids through intramolecular [3 + 2] cycloadditions. A preliminary study

  已经开发了一种实用的伸缩三步法，用于从相应的1,2-二醇合成α-氨基酸。该方法能够直接合成游离的α-氨基酸，而无需任何保护/脱保护步骤。该方法对于制备15 N标记的α-氨基酸也是有效的。带有α，β-不饱和酯部分的1,2-二醇通过分子内[3 + 2]环加成反应提供双环α-氨基酸。初步研究表明，所得的α-氨基酸几乎可以完全被氨基酰基分解。
• Selective cleavage of acetals with ZnBr2 in dichloromethane
  作者：Celia Ribes、Eva Falomir、Juan Murga

  DOI：10.1016/j.tet.2005.10.064

  日期：2006.2

  A selective cleavage of acetals of 1,2- and 1,3-diols has been achieved under mild conditions using ZnBr2 in dichloromethane at room temperature. Acetal types cleavable by this procedure include benzylidene, isopropylidene and cyclohexylidene acetals. This method is compatible with several other types of hydroxyl protecting groups such as Bn, Bz, TBDPS, TIPS and TBDMS. (c) 2005 Published by Elsevier Ltd.