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
• Article Data: 10

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

• 52783-53-6 methyl 2,3,3'-tri-O-benzoyl-β-D-apiofuranoside 
• 58510-41-1 di-O-benzoyl-1,2-O-(α-methoxybenzylidene)-α-D-ribofuranose 
• 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 
• 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

• 175877-63-1 (R)-2,3-dibenzyloxypropyl 5-bromo-5-deoxy-2,3-O-isopropylidene-β-D-riboside 
• 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 
• 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.

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.

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.