53829-44-0

Basic information

• Product Name: .beta.-D-Glucofuranoside, phenyl 1-thio-
• Synonyms: .beta.-D-Glucofuranoside, phenyl 1-thio-
• CAS NO: 53829-44-0
• Molecular Formula: C12H16O5S
• Molecular Weight: 272.32
• Mol File: 53829-44-0.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: .beta.-D-Glucofuranoside, phenyl 1-thio-(CAS DataBase Reference)
• NIST Chemistry Reference: .beta.-D-Glucofuranoside, phenyl 1-thio-(53829-44-0)
• EPA Substance Registry System: .beta.-D-Glucofuranoside, phenyl 1-thio-(53829-44-0)

Safety Data

• Hazardous Substances Data: 53829-44-0(Hazardous Substances Data)

Upstream product

• 108-98-5 thiophenol 
• 1242450-65-2 1,2,3,4,6-penta-O-acetyl-D-altropyranose 
• 1606161-49-2 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-altropyranoside 
• 1606161-52-7 C₂₀H₂₄O₉S 
• 55123-31-4 1,2,3,5,6-penta-O-acetyl-α,β-D-glucofuranose 
• 514847-46-2 2′-benzimidazolyl 1-thio-β-D-galactofuranoside 
• 5531-53-3 1,2,3,5,6-penta-O-acetyl-α,β-D-galactofuranose 
• 207131-41-7 phenyl 2,3,5,6-tetra-O-acetyl-1-thio-β-D-galactofuranoside 
• 17314-33-9 tributyltin phenyl sulfide 
• 294638-87-2 1,2,3,5,6-penta-O-propanoyl-β-D-glucofuranose 
• 13992-23-9 (2R,3S,4S,5R)-6,6-bis(phenylthio)hexane-1,2,3,4,5-pentaol 
• 14149-69-0 (2R,3R,4S)-6,6-bis(phenylthio)hexane-1,2,3,4,5-pentaol 

Downstream Products

• 1606161-55-0 phenyl 1-thio-6-O-triisopropylsilyl-α-D-altropyranoside 
• 1606161-56-1 C₂₁H₃₆O₅SSi 

Relevant articles and documents

Total Synthesis of the Repeating Unit of Bacteroides fragilis Zwitterionic Polysaccharide A1

Zwitterionic polysaccharides isolated from commensal bacteria are endowed with unique immunological properties and are emerging as immunotherapeutic agents as well as vaccine carriers. Reported herein is a total synthesis of the repeating unit of Bacteroides fragilis zwitterionic polysaccharide A1 (PS A1). The structurally complex tetrasaccharide unit contains a rare sugar 2-acetamido-4-amino-2,4,6-trideoxy-d-galactose (AAT) and two consecutive 1,2-cis glycosidic linkages. The repeating unit was efficiently assembled by rapid synthesis of d-galactosamine and AAT building blocks from cheap and abundant d-mannose via a one-pot SN2 displacement of 2,4-bistriflates and installation of all of the glycosidic bonds in a highly stereoselective manner. The total synthesis involves a longest linear sequence of 17 steps with 3.47% overall yield.

NEW ANTIBACTERIAL COMPOUNDS AND BIOLOGICAL APPLICATIONS THEREOF

The invention relates to compounds of formulae (Ia), (Ib) or (Ic) wherein, - A1 and A2, identical or different, are H, (C1-C6) alkyl, (C1-C6) fluoroalkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, (C1-C6) alkyl-ORa, (C1-C6) alkyl-SRa, (C1-C6) alkyl-NRaRb, ORa, SRa, NRaRb, or CORa; - A3 is H, OH or form a carbonyl with A4; - A4 is H, OH or form a carbonyl with A3; - A5 is H, CRaRbOH, F, OH or forms a double bond with X in the case where X is CH; - A6 is H or F; - X is CH2, CHF, CF2, CHOH, O, S, NRa or a simple bond, or X is CH in the case where A5 forms with X a double bond; - Y is P(O) (ORa) (ORb) or P (O) (ORa) (NRaRb); - V is O or S; - A7 is H, (C1-C6) alkyl, (C1-C6) fluoroalkyl, (C2-C6) alkenyl, (C2-C6) alkynyl or (C1-C6) alkyl-ORa; - A8 is OH or H, - Ra and Rb, identical or different, are H, (C1-C6) alkyl, (C1-C6) fluoroalkyl, (C1-C6) alkyl-OH or (C1-C6) alkyl-O- (C1- C6) alkyl; and their addition salts thereof with acids and bases, their preparation and their use in the antibacterial prevention and therapy, used alone or in association with antibacterials, antivirulence agents or drugs reinforcing the host innate immunity.

Glucofuranoses

A β-D-glucofuranose compound which is 1,2,3,5,6-penta-O-propanoyl-β-D-glucofuranose, preferably in crystalline form, is prepared from D-glucose. The compound is prepared by reacting D-glucose with boric acid, or an equivalent thereof, followed by treatment with a propanoylating reagent, preferably propanoic anhydride. The compound is useful for the preparation of other compounds, such as glucofuranosides.