38838-05-0

Basic information

• Product Name: Methyl 5-bromo-5-deoxy-2,3-O-isopropylidene-beta-D-ribofuranoside
• Synonyms: EINECS 254-145-1
• CAS NO: 38838-05-0
• Molecular Formula: C₉H₁₅BrO₄
• Molecular Weight: 267.12
• Mol File: 38838-05-0.mol

Chemical Properties

• Boiling Point: 295.4°Cat760mmHg
• Flash Point: 118.4°C
• Density: 1.47g/cm³
• CAS DataBase Reference: Methyl 5-bromo-5-deoxy-2,3-O-isopropylidene-beta-D-ribofuranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 5-bromo-5-deoxy-2,3-O-isopropylidene-beta-D-ribofuranoside(38838-05-0)
• EPA Substance Registry System: Methyl 5-bromo-5-deoxy-2,3-O-isopropylidene-beta-D-ribofuranoside(38838-05-0)

Safety Data

• Hazardous Substances Data: 38838-05-0(Hazardous Substances Data)

Upstream product

• 532-20-7 D-Ribose 
• 50610-99-6 1-O-methyl-2,3-O-isopropylidene-5-O-(methanesulfonyl)-β-D-ribofuranoside 
• 7473-45-2 1-O-methyl-D-ribofuranose 
• 58510-41-1 di-O-benzoyl-1,2-O-(α-methoxybenzylidene)-α-D-ribofuranose 
• 52783-53-6 methyl 2,3,3'-tri-O-benzoyl-β-D-apiofuranoside 
• 118190-81-1 methyl (methyl 5-deoxy-2,3-O-isopropylidene-β-D-ribo-hexafuranosid)uronate 
• 36468-53-8 β-D-ribofuranose 
• 4137-56-8 methyl 2,3-O-isopropylidene-5-O-p-tolylsulfonyl-β-D-ribofuranoside 
• 123455-86-7 Pyridine-2-sulfonic acid (3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester 
• 85558-05-0 2-((3aR,4R,6R,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethoxy)-1,3-diphenyl-[1,3,2]diazaphospholidine 
• 4099-85-8 ((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 54623-00-6 (methyl 5-deoxy-2,3-O-isopropylidene-methyl-β-D-ribo-hexafuranoside)uronic acid 

Downstream Products

• 27821-07-4 1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose 
• 158112-55-1 5-O-deoxy-D-ribofuranose 
• 370860-10-9 (R)-2,3-dibenzyloxypropyl 5-deoxy-5-dimethylarsino-2,3-O-isopropylidene-β-D-riboside 
• 175877-63-1 (R)-2,3-dibenzyloxypropyl 5-bromo-5-deoxy-2,3-O-isopropylidene-β-D-riboside 
• 23202-81-5 methyl 5-deoxy-2,3-O-isopropylidene-β-D-ribofuranoside 
• 4099-85-8 ((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 

Relevant articles and documents

Revisiting synthetic preparation of the quorum sensing substrate S-d-ribosyl-l-homocysteine (SRH)

Cleavage of the thioether bond of S-d-ribosyl-l-homocysteine (SRH) by the enzyme S-ribosylhomocysteinase (LuxS) serves as the final biosynthetic step in the generation of the quorum sensing autoinducer AI-2 by bacteria. Herein, a revised chemical synthesis of SRH is presented at convenient scale and purity for in vitro studies of LuxS. Potassium bis(trimethylsilyl)amide (KHMDS) is identified as a judicious base for the formation of the thioether of the target compound from readily-accessible precursors: a thiol nucleophile derived from l-homocystine and a sulfonate-activated d-ribosyl electrophile. The exclusive use of acid-labile protecting groups allows for facile deprotection to the final product, producing the TFA salt of SRH in five synthetic steps and 26% overall yield. The chemically-synthesized material is isolated at high purity and demonstrated to serve as the LuxS substrate by an in vitro assay.

Reaction of methyl-4-methylene-2,3-O-isopropylidene-β-D-ribofuranoside with N-bromosuccinimide in aqueous tetrahydrofurane

Methyl-4-methylene-2,3-O-isopropylidene-β-D-ribofuranoside prepared from D-ribose reacted in a system NBS-THF-H2O to give a mixture of stereoisomeric products of regioselective bromohydroxylation of a double bond. The reaction involved a hydrolysis of the glycoside bond, but the acetonide protective group was retained. The mechanism of the selective hydrolysis originating from the ring-chain tautomerism of bromohydrins obtained was proved by the 1H NMR spectra of the steroisomeric methyl-5-deoxy-5-bromo-4- hydroxy-2,3-O-isopropylidene-β-D-ribofuranosides. By crotonic cyclization of the formed masked 1,4-dicarbonyl compounds at heating in benzene in the presence of neutral Al2O3 a new chiral cyclopentenone block, 2-bromo-4,5-isopropylideneoxycyclopent-2-en-1-one, was obtained in a low yield. Nauka/Interperiodica 2007.

Structure-property relationships of ribose based ionic liquids

The authors of this work have successfully synthesized a broad choice of new ribose based ionic liquids, using several varying protecting groups (methyl, ethyl, allyl and benzyl) at the various positions of the carbohydrate, as well as different quarternised N-heterocycles and different anions. These consistent variations of the carbohydrate based ionic liquids (CHILs) enabled an extensive structure-property relationship study of thermal properties, allowing the authors to prove existing trends and to find a correlation between the decomposition temperature and the structure of the CHILs.

An improved synthesis of (R)-2,3-dihydroxypropyl 5-deoxy-5-dimethylarsinyl-β-D-riboside, a common marine arsenical

An efficient synthesis of (R)-2,3-dihydroxypropyl 5-deoxy-5-dimethylarsinyl-β-D-riboside, a common marine arsenical, from D-ribose, (S)-2,3-dibenzyloxypropanol and iododimethylarsine is described.

Arsenic-containing Ribosides from the Brown Alga Sargassum lacerifolium: X-Ray Molecular Structure of 2-Amino-3-propane-1-sulphonic Acid

Three novel arsenic-containing ribosides, methyl 5-deoxy-5-(dimethylarsinoyl)-β-D-riboside, 1-O-mannitol, and a dimethylarsonio-β-D-riboside have been isolated from extracts of the brown alga Sargassum lacerifolium.In addition, five previously reported arsenic-containing ribosides, and some arsenate, were isolated from Sargassum, and dimethylarsinic acid was also shown to be present.The compounds were identified chiefly by NMR spectroscopy, and an X-ray molecular structure is reported for one of them, 2-amino-3-propane-1-sulphonic acid.The stereochemistry of the aglycones in these arsenic-containing ribosides is discussed and the configuration of 3--2-hydroxypropane-1-sulphonic acid 4 was assigned as 2S on the basis of a comparison of NMR spectra with those of synthetic model compounds.

DESIGN AND REACTIVITY OF ORGANIC FUNCTIONAL GROUPS - 2-PYRIDYLSULFONATES AS NUCLEOFUGAL ESTERS: REMARKABLY MILD TRANSFORMATIONS INTO HALIDES AND OLEFINS

The novel 2-pyridylsulfonate esters are excellent leaving groups for the preparation of bromides and olefins under very mild reaction conditions.Displacements occur with inversion of configuration.

DESIGN AND REACTIVITY OF ORGANIC FUNCTIONAL GROUPS: THE HIGHLY CRYSTALLINE 2-ALKOXY N,N'-DIPHENYL-1,3,2-DIAZAPHOSPHOLANES AND THEIR FACILE CONVERSION INTO ALKYL HALIDES

Functionalization of alcohols as 2-alkoxy N,N'-diphenyl-1,3,2-diazaphospholanes affords highly crystalline derivatives useful for characterization purposes.These tervalent phosphorus derivatives undergo facile and mild conversion into the corresponding alkyl halides with inversion of configuration.

Conversion of hydroxyl groups into bromo groups in carbohydrates with inversion of configuration

A novel reagent system is described for the efficient, one-step transformation of hydroxyl groups in carbohydrates to bromodeoxy groups.The reaction proceeds with inversion of configuration.The reagent system consists of triphenylphosphine, tribromoimidazole, and imidazole in toluene at elevated temperature.The carbohydrate need not be soluble in toluene.The examples given include substitution of isolated primary and secondary hydroxyl groups in otherwise protected carbohydrates as well as disubstitution involving one primary and one secondary position in hexopyranosides.High yields are obtained in the replacement of hydroxyl by brommine in the 2-position of 3,4,6-protected methyl α-D-gluco- and -mannopyranosides.