methyl 3,5-dinitrosalicylate - CAS 22633-33-6
Catalog number: 22633-33-6
Category: Main Product
Molecular Formula:
Molecular Weight:
Off-white Solid
RARECHEM AL BF 0171; 2-hydroxy-3,5-dinitro-benzoicacimethylester; 3,5-dinitrosalicyclic acid methy ester; 3,5-DINITRO SALICYLIC ACID METHYL ESTER; 3,5-DINITROMETHYLSALICYLATE; METHYL 3,5-DINITROSALICYLATE; METHYL 3,5-DINITRO-2-HYDROXYBENZOATE; 3,5-DNSA-ME
Derivative of Salicylic acid.
Boiling Point:
347.7ºC at 760 mmHg
Melting Point:
1.62 g/cm3
1.Reconsidering glycosylations at high temperature: precise microwave heating.
Larsen K1, Worm-Leonhard K, Olsen P, Hoel A, Jensen KJ. Org Biomol Chem. 2005 Nov 7;3(21):3966-70. Epub 2005 Sep 27.
Current methods for glycosylation of complex alcohols, e.g. with glycosyl trichloroacetimidates, generally occur in the presence of a strong Lewis acid 'promoter', and at sub-ambient temperatures. However, the older literature reports high-temperature glycosylations, especially of phenols. We have described an efficient method for glycosylation of alcohols under neutral conditions, using as anomeric leaving group methyl 3,5-dinitrosalicylate (DISAL). Only a very few reports have described the use of microwaves to promote glycosylations, mainly of simple alcohols. Here we describe fast, high-temperature glycosylations using precise microwave heating in the synthesis of oligosaccharides, with both DISAL and widely used trichloroacetimidate glycosyl donors in the absence of strong Lewis acids. Also, we have applied microwave heating as a general protocol for evaluating new, potential glycosyl donors.
2.DISAL glycosyl donors for the synthesis of a linear hexasaccharide under mild conditions.
Petersen L1, Laursen JB, Larsen K, Motawia MS, Jensen KJ. Org Lett. 2003 Apr 17;5(8):1309-12.
[reaction: see text] The new class of glycosyl donors with a methyl 3,5-dinitrosalicylate (DISAL) anomeric leaving group has proved efficient for glycosylation under strictly neutral, mildly basic, or mildly acidic conditions. Here, we report the synthesis of novel DISAL disaccharide glycosyl donors prepared by easy nucleophilic aromatic substitution. These DISAL donors proved efficient in the synthesis of a starch-related hexasaccharide under very mild conditions. Glycosylations proceeded with alpha-selectivity and were compatible with Trt protecting groups.
3.Efficient synthesis of glycosylated phenazine natural products and analogs with DISAL (methyl 3,5-dinitrosalicylate) glycosyl donors.
Laursen JB1, Petersen L, Jensen KJ, Nielsen J. Org Biomol Chem. 2003 Sep 21;1(18):3147-53.
Inspired by the occurrence and function of phenazines in natural products, new glycosylated analogs were designed and synthesized. DISAL (methyl 3,5-dinitrosalicylate) glycosyl donors were used in an efficient and easily-handled glycosylation protocol compatible with combinatorial chemistry. Benzoylated D-glucose, D-galactose and L-quinovose DISAL glycosyl donors were synthesized in high yields and used under mild conditions to glycosylate methyl saphenate and 2-hydroxyphenazine. The glycosides were screened for biological activity and one compound showed inhibitory activity towards topoisomerase II.
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CAS 22633-33-6 methyl 3,5-dinitrosalicylate

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