131757-84-1

Basic information

• Product Name: methyl 2,3,4,6-tetra-O-benzyl-5-deoxy-5-thio-α-D-glucopyranoside
• Synonyms: methyl 2,3,4,6-tetra-O-benzyl-5-deoxy-5-thio-α-D-glucopyranoside
• CAS NO: 131757-84-1
• Molecular Weight: 570.75
• Mol File: 131757-84-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: methyl 2,3,4,6-tetra-O-benzyl-5-deoxy-5-thio-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3,4,6-tetra-O-benzyl-5-deoxy-5-thio-α-D-glucopyranoside(131757-84-1)
• EPA Substance Registry System: methyl 2,3,4,6-tetra-O-benzyl-5-deoxy-5-thio-α-D-glucopyranoside(131757-84-1)

Safety Data

• Hazardous Substances Data: 131757-84-1(Hazardous Substances Data)

Upstream product

• 139211-78-2 methyl 2,3,4,6-tetra-O-benzyl-5-C-hydroxy-5-thio-α-D-glucopyranoside 
• 139183-40-7 Thioacetic acid S-((2S,3R,4S,5R)-2,3,4,6-tetrakis-benzyloxy-5-methanesulfonyloxy-1-methoxy-hexyl) ester 
• 139183-39-4 2,3,4,6-tetra-O-benzyl-α-D-altrose S-acetyl O-methyl monothioacetal 
• 139241-42-2 methyl 2,3,4,6-tetra-O-benzyl-α-D-altropyranoside 
• 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 
• 10227-17-5 3,6-di-O-acetyl-5-S-acetyl-6-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose 
• 10227-18-6 1,2,3,4,6-penta-O-acetyl-5-thio-α-D-glucopyranoside 
• 139183-42-9 (1S)-2,3,4,6-tetra-O-benzyl-D-xylo-hexos-5-ulose S-acetyl O-methyl monothioacetal 
• 139183-42-9 (1S)-2,3,4,6-tetra-O-benzyl-D-xylo-hexos-5-ulose S-acetyl O-methyl monothioacetal 
• 139183-39-4 (1S)-2,3,4,6-tetra-O-benzyl-D-glucose S-acetyl O-methyl monothioacetal 
• 139183-46-3 (1R)-2,3,4,6-tetra-O-benzyl-D-glucose S-acetyl O-methyl monothioacetal 
• 19488-61-0 methyl 2,3,4,6-tetra-O-benzyl α-D-glucopyranoside 

Downstream Products

• 131757-93-2 1-O-acetyl-2,3,4,6-tetra-O-benzyl-5-thio-α-D-glucopyranose 
• 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 

Relevant articles and documents

Novel conversion of aldopyranosides into 5-thioaldopyranosides via acyclic monothioacetals with inversion and retention of configuration at C-5

A new strategy for synthesis of 5-thioaldopyranosides was developed. This included the ring opening of D-aldopyranosides with dimethylboron bromide and thioacetic acid, giving the acyclic monothioacetals, followed by the intramolecular cyclization between C-5 and 1-S. Cyclization with inversion of configuration at C-5 was achieved by simultaneous S-deacetylation and intramolecular nucleophilic substitution of the 5-methanesulfonylated monothioacetal to give 5-thio-L-aldopyranosides. The 5-hydroxymonothioacetal underwent cyclization with the Mitsunobu reagents to give the same 5-thio-L-aldopyranosides. Syntheses of 5-thio-D-glucopyranosides were achieved by double inversion of C-5. The glycos-5-ulose derivatives of the monothioacetals spontaneously cyclized on S-deacetylation to give 5-C-hydroxyl-5-thio-D-glucopyranosides, which were deoxygenated at C-5 to give 5-thio-D-glucopyranosides, with net retention of configuration at C-5 from the monothioacetal. Stereoselective reduction of the glycos-5-ulose followed by intramolecular cyclization with the Mitsunobu reagents also gave 5-thio-D-glucopyranosides. The strategy for L enantiomers was applied to the synthesis of 5-thio-L-galactose. The inhibitory effect of 5-thio-L-galactose toward α-L-fucosidase (K(i) 960 μM) is also reported.

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-