214272-33-0

Basic information

• Product Name: 4-(5-Thio-beta-D-xylopyranosylsulfanyl)benzothioimidic acid S-methyl ester hydroiodide
• Synonyms: GYKI-39521; RGH-1875
• CAS NO: 214272-33-0
• Molecular Formula: C₁₃H₁₈INO₃S₃
• Molecular Weight: 459.38971
• Mol File: 214272-33-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 4-(5-Thio-beta-D-xylopyranosylsulfanyl)benzothioimidic acid S-methyl ester hydroiodide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(5-Thio-beta-D-xylopyranosylsulfanyl)benzothioimidic acid S-methyl ester hydroiodide(214272-33-0)
• EPA Substance Registry System: 4-(5-Thio-beta-D-xylopyranosylsulfanyl)benzothioimidic acid S-methyl ester hydroiodide(214272-33-0)

Safety Data

• Hazardous Substances Data: 214272-33-0(Hazardous Substances Data)

Upstream product

• 6893-65-8 1,2-di-O-isopropylidene-5-O-tosyl-D-xylofuranose 
• 214272-23-8 1R,2S,4S,7R,9R-3,5,8,10,12-pentaoxa-4-thia-11-dimethyl-tricyclo[7,3,0,0^2,7]-dodecane S-oxide 
• 214272-22-7 1R,2S,4R,7R,9R-3,5,8,10,12-pentaoxa-4-thia-11-dimethyl-tricyclo[7,3,0,0^2,7]-dodecane S-oxide 
• 214272-20-5 Benzoic acid (3aR,5S,6R,6aR)-5-benzoylsulfanylmethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 
• 214272-25-0 1,2-O-isopropylidene-α-d-xylofuranose 3,5-cyclic sulfate 
• 130783-15-2 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl trichloroacetimidate 
• 210815-67-1 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranose 
• 130782-54-6 4-cyanophenyl 1,5-dithio-β-D-arabinopyranoside 
• 69434-49-7 3-O-benzoyl-1,2-O-isopropylidene-5-O-p-toluenesulfonyl-α-D-xylofuranose 
• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 36801-01-1 4-cyanobenzenethiol 
• 4539-84-8 1,2,3,4-tetra-O-acetyl-5-thio-α-D-xylopyranose 
• 4539-89-3 methyl 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranoside 
• 87-72-9 D-Xylose 

Relevant articles and documents

An economic synthesis of 1,2,3,4-tetra-O-acetyl-5-thio-D-xylopyranose and its transformation into 4-substituted-phenyl 1,5-dithio-D-xylopyranosides possessing antithrombotic activity

D-Xylose was converted via 1,2-O-isopropylidene-α-D-xylofuranose (4) into 3-O-benzoyl-5-S-benzoyl- 1,2-O-isopropylidene-α-D-xylofuranose which, after methanolysis, acetylation and subsequent acetolysis afforded 1,2,3,4-tetra-O-acetyl-5-thio-α-D-xylopyranose (14) in an overall yield of 36%. Reaction of 4 with thionyl chloride gave a mixture of the diastereomeric cyclic sulfites, the structures of which were established by X-ray crystallography. Their oxidation with sodium periodate afforded the corresponding cyclic sulfate 23. Treatment of 23 with potassium thioacetate gave the potassium salt of 5-S-acetyl-1,2-O-isopropylidene-α-D-xylofuranose 3-O-sulfonic acid (26) which, after methanolysis, acetylation and subsequent acetolysis afforded 14 in an overall yield of 56%. Treatment of 4 with sulfuryl chloride gave a mixture containing 5-chloro-3-O-chlorosulfonyl-5-deoxy-1, 2-O-isopropylidene-α-D-xylofuranose, 3,7,9,11-tetraoxa-4-thia-10-dimethyl-tricyclo[6,3,0,02,6]undecane S-dioxide and 23 in a 2:3:7 ratio. Tetraacetate 14 was converted into the α-1-bromide 18 as well as into the α-1-O-trichloroacetimidate 17. These three compounds were used as donors for the glycosylation with 4-cyanothiophenol, affording the 4-cyanophenyl 2,3,4-tri-O-acctyl-1,5-dithio-α- (29) and β-D-xylopyranoside (30) in different ratios, depending on the reaction conditions, When donor 18 was used in the presence of potassium carbonate, besides 29 and 30 two aryl C-glycosylated-thioglycosides, i.e. 4-cyano-2-(2, 3,4-tri-O-acetyl-5-thio-β-D- xylopyranosyl)phenyl 2,3,4-tri-O-acetpy-1,5-dithio-α- and β-D-xylopyranoside (32 and 33) as well as 4-cyano-2-(2,3,4-tri-O-acetyl-5-thio-β-D-xylopyranosyl)phenyl disulfide 34 could be isolated as byproducts. Deacetylation of 30 with sodium methoxide in methanol afforded, besides 4-cyanophenyl 1,5-dithio-β-D-xylopyranoside (1), the corresponding 4-[(methoxy)(imino)methyl]phenyl glycoside 2. The 4-cyano group of 1 was converted into the 4-aminothiocarbonyl, the 4-(methylthio)(imino)methyl, the 4-amidino and the 4-(imino)(hydrazino)methyl group. All of these glycosides showed a significant antithrombotic activity on rats.