Reactions of nitro sugars. X. Novel furanoside synthesis. Conversion of methyl 6-deoxy-6-nitro-.alpha.-D-glucopyranoside into methyl 3-deoxy-3-nitro-.beta.-L-ribo- and -arabinofuranosides and corresponding amino sugars

Baer, Hans H.; Furic, I.

doi:10.1021/jo01274a010

J. Org. Chem.

1968

DOI: 10.1021/jo01274a010

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Reactions of nitro sugars. X. Novel furanoside synthesis. Conversion of methyl 6-deoxy-6-nitro-.alpha.-D-glucopyranoside into methyl 3-deoxy-3-nitro-.beta.-L-ribo- and -arabinofuranosides and corresponding amino sugars

Hans H. Baer¹,

I. Furic²

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Cited by 10 publications

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A novel synthesis of 3′‐deoxy‐3′‐nitrothymidine via nucleophilic substitution with nitrite anion

Huang

Ragouzeos

Rideout

1995

Journal of Heterocyclic Chem

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Nucleophilic substitution at C3′ of 1‐(2‐deoxy‐5‐O‐trityl‐β‐D‐erythr‐pentofuranosyl)‐2‐methoxy‐5‐methyl‐4(1H)‐pyrimidinone (5) with methyl iodide/triphenylphosphine/diethyl azodicarboxylate gave the expected inverted iodide 6 and minor epimer 7. Treatment of 6 with lithium nitrite/phloroglucinol yielded the desired nitro derivative 8 and subsequent acidic deprotection afforded the title compound 1. This represents a novel method for the introduction of a nitro group into the furanosyl moiety of a nucleoside. The nmr spectroscopic techniques (COSY, NOESY, nOe, HMQC and HMBC) were used to determine the stereochemistry at C3′ of the nucleosides. Spectral analysis of H‐D exchange at the 3′‐position of 1 did not indicate the formation of its epimer 10.

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A novel synthesis of 3′‐deoxy‐3′‐nitrothymidine via nucleophilic substitution with nitrite anion

Huang

Ragouzeos

Rideout

1995

Journal of Heterocyclic Chem

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The cyclization of 3-O-benzyl-6-deoxy-6-nitro-D-glucose and -L-idose to O-benzyldeoxynitroinositols, and epimerizations related thereto

Kovář

Baer

1975

Carbohydrate Research

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Synthesis of branched-chain nitro and amino sugars by the nitromethane route

Rosenthal

Ong

Baker

1970

Carbohydrate Research

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Reactions of nitro sugars. X. Novel furanoside synthesis. Conversion of methyl 6-deoxy-6-nitro-.alpha.-D-glucopyranoside into methyl 3-deoxy-3-nitro-.beta.-L-ribo- and -arabinofuranosides and corresponding amino sugars

Cited by 10 publications

References 0 publications

A novel synthesis of 3′‐deoxy‐3′‐nitrothymidine via nucleophilic substitution with nitrite anion

A novel synthesis of 3′‐deoxy‐3′‐nitrothymidine via nucleophilic substitution with nitrite anion

The cyclization of 3-O-benzyl-6-deoxy-6-nitro-D-glucose and -L-idose to O-benzyldeoxynitroinositols, and epimerizations related thereto

Synthesis of branched-chain nitro and amino sugars by the nitromethane route

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