10227-17-5

Basic information

• Product Name: 3,6-Di-O-acetyl-5-Deoxy-5-S-acetyl-1,2-O-isopropylidene-a-D-glucofuranose
• Synonyms: 3,6-Di-O-acetyl-5-Deoxy-5-S-acetyl-1,2-O-isopropylidene-a-D-glucofuranose;3,6-Di-O-acetyl-5-S-acetyl-5-deoxy-1,2-O-isopropylidene-a-D-glucofuranose
• CAS NO: 10227-17-5
• Molecular Formula: C₁₅H₂₂O₈S
• Molecular Weight: 362.397
• Mol File: 10227-17-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3,6-Di-O-acetyl-5-Deoxy-5-S-acetyl-1,2-O-isopropylidene-a-D-glucofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6-Di-O-acetyl-5-Deoxy-5-S-acetyl-1,2-O-isopropylidene-a-D-glucofuranose(10227-17-5)
• EPA Substance Registry System: 3,6-Di-O-acetyl-5-Deoxy-5-S-acetyl-1,2-O-isopropylidene-a-D-glucofuranose(10227-17-5)

Safety Data

• Hazardous Substances Data: 10227-17-5(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 4118-60-9 5,6-anhydro-1,2-O-isopropylidene-β-L-idofuranose 
• 102029-58-3 3-O-acetyl-6-O-benzoyl-1,2-O-isopropylidene-5-O-methylsulphonyl-α-D-glucofuranose 
• 16713-80-7 3-O-acetyl-1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose 
• 37614-79-2 5,6-anhydro-5,6-epithio-1,2-O-isopropylidene-α-D-glucofuranose 

Downstream Products

• 10470-80-1 1,2,3,4,6-penta-O-acetyl-5-thio-α,β-D-glucopyranose 
• 131757-93-2 1-O-acetyl-2,3,4,6-tetra-O-benzyl-5-thio-α-D-glucopyranose 
• 131757-84-1 methyl 2,3,4,6-tetra-O-benzyl-5-deoxy-5-thio-α-D-glucopyranoside 
• 131757-92-1 (3R,4S,5S,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]tetrahydro-2H-thiopyran-2-one 
• 131757-87-4 5-(benzyloxymethyl)-thiophene-2-carboxaldehyde 
• 16505-91-2 (3R,4S,5S,6R)-6-(hydroxymethyl)tetrahydro-2H-thiopyran-2,3,4,5-tetraol 

Relevant articles and documents

A novel synthesis of 5-thio-D-glucose

A shorter synthesis of 5-thio-D-glucose is described in 8 steps from commercially available D-glucofurano-3,6-lactone.

Synthesis and Evaluation of 1,5-Dithia- d -laminaribiose, Triose, and Tetraose as Truncated β-(1→3)-Glucan Mimetics

The preparation and characterization of a series of di-, tri-, and tetrasaccharide analogues of β-(1→3)-glucans is described in which each pyranoside ring is replaced by a 5-thiopyranosyl ring and each glycosidic oxygen by a thioether. These oligomeric 1,

Novel preparation of (2-azidomethyl)benzoic acid and an application as a protective group

A novel preparation method of 2-(azidomethyl)benzoic acid, a precursor of (2-azidomethyl)benzoyl (AZMB) protective group, was developed which can provide pure sample in gram scale without chromatographic purifications. Reductive cleavage using triphenylphosphine was found to be effective in the case of sterically hindered ester that resists under basic hydrolysis.

Thio-sugars. I. Radical-promoted thione-thiol rearrangement of cyclic thionocarbonates: Synthesis of 5-thioglucose

The 5,6-O-thiocarbonyl-α-D-glucofuranose derivatives 2, when subjected to one of the following reactions, undergo a radical-promoted thione-thiol rearrangement to yield the 5-S-thiolcarbonates of gluco-configuration 8 as the major product. The reactions are, (A) thermolysis with a catalytic amount of tributyltin hydride and AIBN, (B) photolysis with hexabutyldistannane, and (C) thermolysis with dimethyl phosphonate and benzoyl peroxide. On the other hand, thermolysis of 2 with trialkylsilane (condition D) yielded olefins 13 as the major product. The 5-S-gluco product 8 was converted, in three steps, to 5-thioglucose (21) in 55% yield.

Synthesis of Per-O-alkylated 5-Thio-D-glucono-1,5-lactones and Transannular Participation of the Ring Sulphur Atom of 5-Thio-D-glucose Derivatives on Solvolysis under Acidic Conditions

Per-O-alkylated 5-thio-D-glucono-1,5-lactones (33)-(35) were synthesized via acetolysis or hydrolysis of the corresponding methyl glycosides (21)-(23).Transannular participation of the sulphur atom on acid methanolysis of 3,6-di-O-acetyl-5-S-acetyl-1,2-O-