63073-99-4

Basic information

• Product Name: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-mercaptotetrahydro-2H-pyran-3,4,5-triol
• Synonyms: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-mercaptotetrahydro-2H-pyran-3,4,5-triol
• CAS NO: 63073-99-4
• Molecular Weight: 196.224
• Mol File: 63073-99-4.mol
• Article Data: 18

Chemical Properties

• CAS DataBase Reference: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-mercaptotetrahydro-2H-pyran-3,4,5-triol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-mercaptotetrahydro-2H-pyran-3,4,5-triol(63073-99-4)
• EPA Substance Registry System: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-mercaptotetrahydro-2H-pyran-3,4,5-triol(63073-99-4)

Safety Data

• Hazardous Substances Data: 63073-99-4(Hazardous Substances Data)

Upstream product

• 2280-44-6 D-Glucose 
• 73427-33-5 S-nitroso-1-thio-β-D-glucose 
• 6806-56-0 O²,O³,O⁴,O⁶,S-Pentaacetyl-1-thio-β-D-glucopyranose 
• 19879-84-6 tetraacetyl thioglucose 
• 40591-65-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiouronium bromide 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 604-68-2 α-D-glucopyranose peracetylate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 83-87-4 D-glucose pentaacetate 

Downstream Products

• 73427-33-5 S-nitroso-1-thio-β-D-glucose 
• 678968-49-5 phenyl 1-selenylsulfide-β-D-glucopyranoside 
• 130796-15-5 1-S-acetyl-2,3,4,6-tetra-O-acetyl-1-deoxy-1-thio-α-D-galactopyranoside 
• 6806-56-0 2,3,4,6-tetra-O-acetyl-1S-acetyl-1-thio-β-D-galactopyranose 
• 159495-68-8 benzyl 3,4,6-tri-O-acetyl-2-S-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-2-thio-β-D-glucopyranoside 
• 159495-64-4 3-thionigerose 
• 159495-64-4 3-thionigerose 
• 1234504-73-4 C₆₂H₉₄N₁₀O₂₅S₃ 
• 1234504-74-5 C₆₆H₉₆N₁₀O₂₀S₃ 
• 2637-34-5 pyridine-2-thione 
• 1374110-34-5 C₁₁H₁₅NO₅S₂ 
• 96158-82-6 (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[(4-methoxyphenyl)thio]tetrahydro-2H-pyran-3,4,5-triol 
• 1467024-07-2 (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-{[1-(3,4,5-trimethoxyphenyl)vinyl]thio}tetrahydro-2H-pyran-3,4,5-triol 
• 733-11-9 (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-((4-hydroxyphenyl)thio)tetrahydro-2H-pyran-3,4,5-triol 

Relevant articles and documents

Applications of Shoda's reagent (DMC) and analogues for activation of the anomeric centre of unprotected carbohydrates

2-Chloro-1,3-dimethylimidazolinium chloride (DMC, herein also referred to as Shoda's reagent) and its derivatives are useful for numerous synthetic transformations in which the anomeric centre of unprotected reducing sugars is selectively activated in aqueous solution. As such unprotected sugars can undergo anomeric substitution with a range of added nucleophiles, providing highly efficient routes to a range of glycosides and glycoconjugates without the need for traditional protecting group manipulations. This mini-review summarizes the development of DMC and some of its derivatives/analogues, and highlights recent applications for protecting group-free synthesis.

Glycosyl Bunte Salts: A Class of Intermediates for Sugar Chemistry

S-Glycosyl thiosulfates have been discovered as a new class of synthetic intermediates in sugar chemistry, named "glycosyl Bunte salts" after 19th-century German chemist, Hans Bunte. The synthesis was achieved by direct condensation of unprotected sugars and sodium thiosulfate using a formamidine-type dehydrating agent in water-acetonitrile mixed solvent. The application of glycosyl Bunte salts is demonstrated with transformation reactions into other glycosyl compounds such as a 1-thio sugar, a glycosyl disulfide, a 1,6-anhydro sugar, and an O-glycoside.

Stereoretentive palladium-catalyzed arylation, alkenylation, and alkynylation of 1-thiosugars and thiols using aminobiphenyl palladacycle precatalyst at room temperature

A general and efficient protocol for the palladium-catalyzed functionalization of mono- and polyglycosyl thiols by using the palladacycle precatalyst G3-XantPhos was developed. The C-S bond-forming reaction was achieved rapidly at room temperature with various functionalized (hetero)aryl-, alkenyl-, and alkynyl halides. The functional group tolerance on the electrophilic partner is typically high and anomer selectivities of thioglycosides are high in all cases studied. New sulfur nucleophiles such as thiophenols, alkythiols, and thioaminoacids (cysteine) were also successfully coupled to lead to the most general and practical method yet reported for the functionalization of thiols.