74405-35-9

Basic information

• Product Name: 1-(2,2-dimethyl-1,3-dioxolan-4-yl)-3,3-bis(ethylsulfanyl)propane-1,2-diol (non-preferred name)
• CAS NO: 74405-35-9
• Molecular Formula: C₁₂H₂₄O₄S₂
• Molecular Weight: 296.4466
• Mol File: 74405-35-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 441.3°C at 760 mmHg
• Flash Point: 220.7°C
• Density: 1.18g/cm³
• Vapor Pressure: 1.21E-09mmHg at 25°C
• Refractive Index: 1.531
• CAS DataBase Reference: 1-(2,2-dimethyl-1,3-dioxolan-4-yl)-3,3-bis(ethylsulfanyl)propane-1,2-diol (non-preferred name)(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,2-dimethyl-1,3-dioxolan-4-yl)-3,3-bis(ethylsulfanyl)propane-1,2-diol (non-preferred name)(74405-35-9)
• EPA Substance Registry System: 1-(2,2-dimethyl-1,3-dioxolan-4-yl)-3,3-bis(ethylsulfanyl)propane-1,2-diol (non-preferred name)(74405-35-9)

Safety Data

• Hazardous Substances Data: 74405-35-9(Hazardous Substances Data)

Usage

General Description

1-(2,2-dimethyl-1,3-dioxolan-4-yl)-3,3-bis(ethylsulfanyl)propane-1,2-diol, also known as bis(2-ethylthio-2-methyl-1,3-dioxolan-4-yl)propan-2-ol, is a chemical compound with the molecular formula C13H26O4S2. It is a colorless liquid with a faint odor, and it is mainly used as a solvent in various industrial processes. This chemical has potential use as a precursor or intermediate in the synthesis of other organic compounds, and its properties make it suitable for applications in the pharmaceutical industry as well. However, its non-preferred name suggests that it may not be commonly used or recognized by this specific name in scientific literature or industrial applications. Overall, this chemical compound has potential industrial and pharmaceutical uses, but its wider recognition may require the use of a different, more common name.

Upstream product

• 43179-48-2 L-arabinose di(ethylthio)acetal 
• 5328-37-0 L-arabinose 
• 92936-93-1 (4R,5S)-4-(bis(ethylthio)methyl)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-1,3-dioxolane 
• 77-76-9 2,2-dimethoxy-propane 
• 67-64-1 acetone 

Downstream Products

• 75858-37-6 2,3-di-O-benzyl-4,5-O-isopropylidene-L-arabinose diethyldithioacetal 
• 14347-78-5 1,2-O-isopropylidene-D-glycerol 
• 22323-80-4 (4S)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde 
• 1224111-89-0 (1'S,2'S,3'R,4'S)-5-[2'-benzyloxy-3'-tert-butyldimethylsilyloxy-4',5'-dihydroxy-1'-(1H-indol-3-yl)-4',5'-di-O-isopropylidene-pentan-1'-yl]-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 1224111-90-3 (1'R,2'S,3'R,4'S)-5-[2'-benzyloxy-3'-tert-butyldimethylsilyloxy-4',5'-dihydroxy-1'-(1H-indol-3-yl)-4',5'-di-O-isopropylidene-pentan-1'-yl]-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 75858-29-6 (E)-(5S,6R)-5,6-Bis-benzyloxy-6-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hex-2-enoic acid methyl ester 
• 75858-30-9 (E)-(5S,6S,7S)-5,6-Bis-benzyloxy-7,8-dihydroxy-oct-2-enoic acid methyl ester 
• 106180-12-5 5-acetamido-6-O-benzyl-5-deoxy-1,2:7,8-di-O-isopropylidene-3-O-methylthiomethyl-β-L-erythro-L-talooctofuranose-(1,4) 
• 106191-26-8 5-acetamido-6-O-benzyl-5-deoxy-1,2:7,8-di-O-isopropylidene-3-O-methylthiomethyl-β-L-erythro-D-allooctofuranose-(1,4) 
• 75858-28-5 2,3-di-O-benzyl-4,5-O-isopropylidene-aldehydo-L-arabinose 
• 948039-10-9 methyl 2-O-acetyl-3-O-benzyl-5-O-tert-butyl(dimethyl)silyl-L-iduronate di(ethylthio)acetal 
• 875576-52-6 methyl 2-O-acetyl-3-O-benzyl-5-O-tert-butyl(dimethyl)silyl-D-glucuronate di(ethylthio)acetal 
• 875576-41-3 2-O-acetyl-3-O-benzyl-L-arabinose di(ethylthio)acetal 
• 875576-43-5 (2R,3R)-3-acetoxy-2-benzyloxy-4,4-bis(ethylthio)butanal 

Relevant articles and documents

Short de novo synthesis of fully functionalized uronic acid monosaccharides

(Chemical Equation Presented) Short and Sweet: A convergent route leads to orthogonally protected D-glucuronic and L-iduronic acid thioglycoside building blocks, commonly used in heparin oligosaccharide assembly (see scheme). Rapid access to substantial q

Synthesis of 4-cyanophenyl 4-azido-4-deoxy-1,5-dithio-β-D-xylopyranoside

L-Arabinose diethyl dithioacetal was converted, via its 4-azido-5-S-benzoyl-4-deoxy-2,3-O-isopropylidene-5-thio-D-xylose diethyl dithioacetal, into 4-azido-4-deoxy-5-thio-α-D-xylopyranose triacetate 29. Glycosidation of 29 with 4-cyanothiophenol in the presence of trimethylsilyl triflate gave the 4-cyanophenyl 2,3-di-O-acetyl-4-azido-4-deoxy-1,2-dithio-α- and -β-D-xylopyranosides 31 and 33 as well as 3-O-acetyl-2,5-anhydro-4-azido-4-deoxy-5- thio-D-lyxose bis(4-cyanophenyl) dithioacetal 34 in a 8:2:1 respective ratio. Treatment of 29 with hydrogen bromide in acetic acid yielded a 1:4 mixture of 2,3-di-O-acetyl-4-azido-4-deoxy-5-thio-D-xylopyranosyl bromide 38 and 2,3 -di-O-acetyl-5-bromo-5-deoxy-4-thio-L-arabinofuranosyl bromide 40. Reaction of the mixture of bromides 38 and 40 with 4-cyanothiophenol in the presence of potassium carbonate afforded the expected 31 and 33 only in traces, while 2-(1R,2S,-1,2-di-O-acetyl-1,2-dihydroxy-but-3-en-1-yl)-5-cyano-1,3 dithiole and 4-cyanophenyl 2,3-di-O-acetyl-5-S-(4-cyanophenyl)-1,4,5-trithio-α-L-arabinofuranoside (42) were isolated in 18% and 20% yield, respectively. The formation of these two derivatives is tentatively explained by involvement of a radical reaction mechanism. When O-(2,3-di-O-acetyl-4-azido-4-deoxy-5-thio-α-D-xylopyranosyl) trichloroacetimidate was used as donor and boron trifluoride ethyl etherate as promoter, 31 and 33 were formed in excellent yield (96%) in a 2:1 ratio. The glycosides, obtained on deacetylation of 33, 34, and 42 showed a significant antithrombotic activity on rats.

Crystalline 2,3:4,5-di-O-isopropylidene-DL-arabinose diethyl dithioacetal: some reactions of acetal derivatives of arabinose.

Acetonation of the diethyl dithioacetals of D- and L-arabinose gives the corresponding 2,3:4,5-diisopropylidene acetals (2a and 2b) as oils having [alpha]D +82 and -81 degrees, respectively; in admixture, the enantiomers form a well crystallized racemate, m.p. 43-45 degrees. The initial product of acetonation is the 4,5-monoisopropylidene acetal. Demercaptalation of 2a with mercury(II) chloride-cadmium carbonate gives 2,3:4,5-di-O-isopropylidene-aldehydo-D-arabinose (5) in high yield, but the literature procedure employing mercury(II) chloride-mercury(II) oxide affords a mixture of 5 and 1,2:3,4-di-O-isopropylidene-beta-D-arabinopyranose (6). A trace of acid readily and completely converts the aldehydo derivative 5 into the cyclic diacetal 6.