1320337-31-2

Basic information

• Product Name: benzyl 4,6-di-O-acetyl-2,3-dideoxy-3-ethylthio-α-D-arabino-hexopyranoside
• Synonyms: benzyl 4,6-di-O-acetyl-2,3-dideoxy-3-ethylthio-α-D-arabino-hexopyranoside
• CAS NO: 1320337-31-2
• Molecular Weight: 382.478
• Mol File: 1320337-31-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: benzyl 4,6-di-O-acetyl-2,3-dideoxy-3-ethylthio-α-D-arabino-hexopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl 4,6-di-O-acetyl-2,3-dideoxy-3-ethylthio-α-D-arabino-hexopyranoside(1320337-31-2)
• EPA Substance Registry System: benzyl 4,6-di-O-acetyl-2,3-dideoxy-3-ethylthio-α-D-arabino-hexopyranoside(1320337-31-2)

Safety Data

• Hazardous Substances Data: 1320337-31-2(Hazardous Substances Data)

Upstream product

• 60470-15-7 benzyl tert-butyl carbonate 
• 100-51-6 benzyl alcohol 
• 2873-29-2 D-glucal triacetate 

Downstream Products

• 1400879-07-3 (S_S)-benzyl 2-O-methyl-3-deoxy-(3-ethylsulfinyl)-α-D-manno-pyranoside 
• 1400879-04-0 benzyl 4,6-di-O-acetyl-2,3-dideoxy-(3-ethylthio)-α-D-erythro-hex-2-enopyranoside 

Relevant articles and documents

Reactivity switching and selective activation of C-1 or C-3 in 2,3-unsaturated thioglycosides

Reactivity switching and selective activation of C-1 or C-3 in 2,3-unsaturated thioglycosides, namely, 2,3-dideoxy-1-thio-d-hex-2- enopyranosides are reported. The reactivity switching allowed activation of either C-1 or C-3, with the use of either N-iodosuccinimide (NIS)/triflic acid (TfOH) or TfOH alone. C-1 glycosylation with alcohol acceptors occurred in the presence of NIS/TfOH, without the acceptors reacting at C-3. On the other hand, reaction of 2,3-unsaturated thioglycosides with alcohols mediated by triflic acid led to transposition of C-1 ethylthio-moiety to C-3 intramolecularly, to form 3-ethylthio-glycals. Resulting glycals underwent glycosylation with alcohols to afford 3-ethylthio-2-deoxy glycosides. However, when thiol was used as an acceptor, only a stereoselective addition at C-3 resulted, so as to form C-1, C-3 dithio-substituted 2-deoxypyranosides.