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Volumn , Issue 11, 2009, Pages 1809-1811

A mild, highly efficient, and chemoselective deprotection of trityl ethers of carbohydrates and nucleosides using iodine monobromide

(2) Malik, Satish a Kartha, K P Ravindranathan a

a NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER (India)

Author keywords

Carbohydrate; Chemoselective deprotection; Interhalogen; Iodine monobromide; Nucleoside; Trityl ether

Indexed keywords

6 O TRITYL GLUCOSIDE; ACETAL; ACETONITRILE; BROMINE DERIVATIVE; CARBOHYDRATE; DICHLOROMETHANE; ETHER DERIVATIVE; GALACTOPYRANOSYL DERIVATIVE; GLUCOSIDE; IODINE DERIVATIVE; IODINE MONOBROMIDE; METHANOL; NUCLEOSIDE; PYRANOSIDE; TRITYL DERIVATIVE; TRITYL ETHER DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; CONCENTRATION (PARAMETERS); DEPROTECTION REACTION; DETRITYLATION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 67649908649 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0029-1217356 Document Type: Article

Times cited : (10)

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- The workup and isolation of the product are also a lot more convenient in the present case as the literature method3 makes use of glacial AcOH as the solvent for the reaction
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21
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- Typical Procedure for Conversion of 3 → 4 Method A IBr (1.2 mL of a 1 M soln in CH2Cl2, 1.2 mmol) was added to a soln of 3 (562 mg, 1 mmol) in MeCN (10 mL) and was stirred until TLC (EtOAc-hexanes, 2:3) showed completion of the reaction. The reaction mixture was then diluted with CH2Cl2 and was washed successively with dilute aq Na2S2O3 and Na2CO 3 soln, dried (Na2SO4, concentrated to dryness under reduced pressure and was purified by column chromatography (silica gel; EtOAc-hexanes, 2:3) to yield crystals (308 mg, 95, of 4. Alternatively, after the completion of the reaction, the workup can also be carried out by stirring the reaction mixture with Amberlite IRA-400 (hydroxide form) resin to get a colourless solution. Filtration, concentration of the filtrate under reduced pressure, and chromatography as described above afforded 4. Meth
- 2-MeOH (9:1) was used as the solvent instead of MeCN. The product was obtained in practically the same yield.

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