71769-38-5

Basic information

• Product Name: 1-deoxy-2,3-o-isopropylidene-1-tosyl-D-arabinitol
• Synonyms: 1-deoxy-2,3-o-isopropylidene-1-tosyl-D-arabinitol
• CAS NO: 71769-38-5
• Molecular Weight: 386.466
• Mol File: 71769-38-5.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 1-deoxy-2,3-o-isopropylidene-1-tosyl-D-arabinitol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-deoxy-2,3-o-isopropylidene-1-tosyl-D-arabinitol(71769-38-5)
• EPA Substance Registry System: 1-deoxy-2,3-o-isopropylidene-1-tosyl-D-arabinitol(71769-38-5)

Safety Data

• Hazardous Substances Data: 71769-38-5(Hazardous Substances Data)

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 84709-41-1 2,3:4,5-di-O-isopropylidene-D,L-xylitol 
• 50-69-1 D-ribose 
• 488-81-3 Adonitol 
• 3969-86-6 1,2:3,4-Di-O-isopropylidene-DL-ribitol 
• 10323-20-3 D-Arabinose 
• 488-82-4 D-Arabitol 
• 3969-59-3 mannitol triacetonide 
• 38145-93-6 1,2:3,4-di-O-isopropylidene-D-mannitol 
• 13039-93-5 2,2:4,5-di-O-isopropylidene-D-arabinose 
• 19139-74-3 2,3:4,5-di-O-isopropylidene-D-arabinitol 
• 87-99-0 XYLITOL 

Downstream Products

• 69434-51-1 1-(Adenin-9-yl)-1-deoxy-DL-ribitol 
• 223558-75-6 tert-Butyl-diphenyl-((Z)-(S)-1-vinyl-pentadec-7-ene-2,4-diynyloxy)-silane 
• 209479-87-8 tert-Butyl-((S)-3,3-dibromo-1-vinyl-allyloxy)-diphenyl-silane 
• 209479-88-9 tert-butyl((S)-1-penten-4-yn-3-yloxy)diphenylsilane 
• 81203-57-8 (3S,9Z)-1,9-heptadecadiene-4,6-diyn-3-ol 
• 18524-19-1 (S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-prop-2-en-1-ol 
• 69434-51-1 1-(Adenin-9-yl)-1-deoxy-DL-xylitol 

Relevant articles and documents

Phosphite-thioether/selenoether Ligands from Carbohydrates: An Easily Accessible Ligand Library for the Asymmetric Hydrogenation of Functionalized and Unfunctionalized Olefins

A large family of phosphite-thioether/selenoether ligands has been easily prepared from accessible L-(+)-tartaric acid and D-(+)-mannitol and applied in the M-catalyzed (M=Ir, Rh) asymmetric hydrogenation of a broad number of substrates (46 in total). Its highly modular architecture has been crucial to maximize the catalytic performance. Improving most of the reported approaches, this ligand family presents a broad substrate scope. By selecting the ligand parameters high enantioselectivities (ee's up to 99 %) have therefore been achieved in a broad range of both, functionalized and unfunctionalized substrates. Interestingly, both enantiomers of the hydrogenation products can be usually achieved by changing the ligand parameters.

Absolute configuration of falcarinol, a potent antitumor agent commonly occurring in plants

The absolute configuration of falcarinol (1) was established by stereoselective total synthesis of the two enantiomers.

Hydrolysis of (2-deoxy-β-D-glucopyranosyl)pyridinium salts

The hydrolysis reactions of three (2-deoxy-β-D-glucopyranosyl)pyridinium salts exhibit first-order rate constants that are independent of pH in the range of 4.4-10.1 pH units. Derived second-order rate constants for the hydrolysis reactions of (2-deoxy-β-D-glucopyranosyl)-4′-bromoisoquinolinium bromide (5b) conducted in the presence of nucleophilic monoanions (μ = 2.0) including AcO-, Cl-, Br-, and N3 exhibit a Swain-Scott parameter (s) of 0,03 ± 0.05, indicating that these reactions show no sensitivity to the nature of the anion. However, a substantial quantity of the (2-deoxyglucopyranosyl)pyridinium salt hydrolysis product is formed as a result of a post-rate-limiting reaction involving a nucleophilic anion. Analysis of the product ratios indicates that the first-formed intermediate in the hydrolytic reaction is a solvent-separated ion painmolecule encounter complex. The data allow a calculated estimate of greater than 2.5 × 10-12 s for the lifetime of the glucopyranosyloxocarbenium ion in aqueous solution.