293751-01-6

Basic information

• Product Name: 3-O-Benzyl4-C-(methanesulfonyloxymethyl)-5-O-methanesulfonyl-1,2-O-isopropylidene-a-D-ribofuranose
• Synonyms: 3-O-Benzyl4-C-(methanesulfonyloxymethyl)-5-O-methanesulfonyl-1,2-O-isopropylidene-a-D-ribofuranose;3-O-benzyl-4-C-(MethanesulfonyloxyMethyl)-5-O-Methanesulfonyl-1,2-O-isopropylidene-α-D-ribofuranose;1,2-O-(1-Methylethylidene)-4-C-[[(methylsulfonyl)oxy]methyl]-3-O-(phenylmethyl)-alpha-D-erythro-pentofuranose 5-methanesulfonate;3-O-Benzyl-4-C-(methane sulphonyloxymethyl)-5-O-methane sulphonyl-1,2-O-isopropylidene-a-D-ribofuranoside;3-O-Benzyl-4-C-(methane sulphonyloxymethyl)-5-O-methane sulphonyl-1,2-O-isopropylidene-α-D-ribofuranoside
• CAS NO: 293751-01-6
• Molecular Formula: C₁₈H₂₆O₁₀S₂
• Molecular Weight: 466.525
• Mol File: 293751-01-6.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-O-Benzyl4-C-(methanesulfonyloxymethyl)-5-O-methanesulfonyl-1,2-O-isopropylidene-a-D-ribofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 3-O-Benzyl4-C-(methanesulfonyloxymethyl)-5-O-methanesulfonyl-1,2-O-isopropylidene-a-D-ribofuranose(293751-01-6)
• EPA Substance Registry System: 3-O-Benzyl4-C-(methanesulfonyloxymethyl)-5-O-methanesulfonyl-1,2-O-isopropylidene-a-D-ribofuranose(293751-01-6)

Safety Data

• Hazardous Substances Data: 293751-01-6(Hazardous Substances Data)

Usage

General Description

3-O-Benzyl-4-C-(methanesulfonyloxymethyl)-5-O-methanesulfonyl-1,2-O-isopropylidene-α-D-ribofuranose is a complex chemical compound with several functional groups attached to a ribofuranose sugar molecule. The benzyl group, methanesulfonyl groups, and isopropylidene group all contribute to its overall structure and reactivity. 3-O-Benzyl4-C-(methanesulfonyloxymethyl)-5-O-methanesulfonyl-1,2-O-isopropylidene-a-D-ribofuranose is often used in organic synthesis as a protecting group for the sugar moiety, allowing for selective manipulation of other functional groups in a molecule. It is an important tool in carbohydrate chemistry for the construction of complex oligosaccharides and glycoconjugates. 3-O-Benzyl4-C-(methanesulfonyloxymethyl)-5-O-methanesulfonyl-1,2-O-isopropylidene-a-D-ribofuranose also has potential applications in the pharmaceutical industry for the development of carbohydrate-based drugs and therapeutics.

Upstream product

• 124-63-0 methanesulfonyl chloride 
• 63593-03-3 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 63593-02-2 3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose 
• 57099-04-4 3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose 
• 22331-21-1 1,2:5,6-di-O-isopropylidene-3-O-benzyl-α-D-allofuranose 
• 100-39-0 benzyl bromide 
• 2595-05-3 Diacetone D-glucose 

Downstream Products

• 378792-34-8 methyl (3-O-benzyl-5-O-methylsulfonyl-4-C-methylsulfonyloxymethyl)-D-ribofuranoside 
• 293751-03-8 1,2-di-O-acetyl-3-O-benzyl-4-C-methanesulfonyloxymethyl-5-O-methanesulfonyl-D-erythro-pentofuranose 
• 552856-42-5 (1R,3R,4R,7S)-7-benzyloxy-1-methanesulfonyloxymethyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane 
• 552856-43-6 (1R,3R,4R,7S)-1-benzoyloxymethyl-7-benzyloxy-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane 
• 552856-44-7 (1R,3R,4R,7S)-7-benzyloxy-1-hydroxymethyl-3-(thymin-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane 
• 1415236-70-2 (1R,3R,4R,7S)-7-benzyloxy-1-hydroxymethyl-3-(thymin-1-yl)-5-trifluoroacetyl-2-oxa-5-azabicyclo[2.2.1]heptane 
• 1262529-23-6 (1R,3R,4R,7S)-7-benzyloxy-1-(4,4'-dimethoxytrityl)oxymethyl-3-(thymin-1-yl)-5-trifluoroacetyl-2-oxa-5-azabicyclo[2.2.1]heptane 
• 1262529-26-9 (1R,3R,4R,7S)-7-benzyloxy-1-(4,4'-dimethoxytrityl)oxymethyl-3-(5-methylcytosin-1-yl)-5-trifluoroacetyl-2-oxa-5-azabicyclo[2.2.1]heptane 
• 1415236-72-4 (1R,3R,4R,7S)-7-benzyloxy-1-(4,4'-dimethoxytrityl)oxymethyl-3-(4-N-benzoyl-5-methylcytosin-1-yl)-5-trifluoroacetyl-2-oxa-5-azabicyclo[2.2.1]heptane 
• 1415236-76-8 (1R,3R,4R,7S)-7-benzyloxy-1-(4,4'-dimethoxytrityl)oxymethyl-3-(4-N-acetyl-5-methylcytosin-1-yl)-5-trifluoroacetyl-2-oxa-5-azabicyclo[2.2.1]heptane 
• 1415236-73-5 (1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-5-(hexadecanoyl)-7-hydroxy-3-(4-N-benzoyl-5-methylcytosine-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane 
• 1415236-77-9 (1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-5-(hexadecanoyl)-7-hydroxy-3-(5-methylcytosine-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane 
• 1415236-74-6 (1R,3R,4R,7S)-7-(2-cyanoethoxy(diisopropylamino)phosphinoxy)-1-(4,4'-dimethoxytrityloxymethyl)-5-(hexadecanoyl)-7-hydroxy-3-(4-N-benzoyl-5-methylcytosine-1-yl)-2-oxa-5-azabicyclo[2.2.1]heptane 
• 293751-07-2 1-(3-O-benzyl-2,5-di-O-methanesulfonyl-4-C-(methanesulfonyloxymethyl)-β-D-erythro-pentofuranosyl)thymine 

Relevant articles and documents

NOVEL PROCESS FOR MAKING ALLOFURANOSE FROM GLUCOFURANOSE

The present invention relates to the manufacture of allofuranose from glucofuranose as defined in the description and in the claim. Allofuranos is an intermediate in the manufacture of oligonucleotides which can be used as a medicament.

Synthesis of 2′-O,4′-C-alkylene-bridged ribonucleosides and their evaluation as inhibitors of HCV NS5B polymerase

The synthesis of 2′-O,4′-C-methylene-bridged bicyclic guanine ribonucleosides bearing 2′-C-methyl or 5′-C-methyl modifications is described. Key to the successful installation of the methyl functionality in both cases was the use of a one-pot oxidation-Grignard procedure to avoid formation of the respective unreactive hydrates prior to alkylation. The 2′-C-methyl- and 5′-C-methyl-modified bicyclic guanosines were evaluated, along with the known uracil-, cytosine-, adenine-, guanine-LNA and guanine-ENA nucleosides, as potential antiviral agents and found to be inactive in the hepatitis C virus (HCV) cell-based replicon assay. Examination of the corresponding nucleoside triphosphates, however, against the purified HCV NS5B polymerase indicated that LNA-G and 2′-C-methyl-LNA-G are potent inhibitors of both 1b wild type and S282T mutant enzymes in vitro. Activity was further demonstrated for the LNA-G-triphosphate against HCV NS5B polymerase genotypes 1a, 2a, 3a and 4a. A phosphorylation by-pass prodrug strategy may be required to promote anti-HCV activity in the replicon assay.

IMPROVED SYNTHESIS OF ?2.2.1|BICYCLO NUCLEOSIDES

A synthesis of [2.2.1]bicyclo nucleosides which is shorter and provides higher overall yields proceeds via the key intermediate of the general formula III, wherein R4 and R5 are, for instance, sulfonates and R7 is, for instance, a halogen or an acetate. F