124915-83-9

Basic information

• Product Name: Methyl 2,3,4-Tris-O-(phenylmethyl)-6,8-dideoxy-7,6-<2-(N,N-dimethylamino)-1-oxa-3-azaprop-2-eno>-1-thio-D-erythro-β-D-galacto-octopyranoside
• Synonyms: Methyl 2,3,4-Tris-O-(phenylmethyl)-6,8-dideoxy-7,6-<2-(N,N-dimethylamino)-1-oxa-3-azaprop-2-eno>-1-thio-D-erythro-β-D-galacto-octopyranoside
• CAS NO: 124915-83-9
• Molecular Weight: 576.757
• Mol File: 124915-83-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Methyl 2,3,4-Tris-O-(phenylmethyl)-6,8-dideoxy-7,6-<2-(N,N-dimethylamino)-1-oxa-3-azaprop-2-eno>-1-thio-D-erythro-β-D-galacto-octopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2,3,4-Tris-O-(phenylmethyl)-6,8-dideoxy-7,6-<2-(N,N-dimethylamino)-1-oxa-3-azaprop-2-eno>-1-thio-D-erythro-β-D-galacto-octopyranoside(124915-83-9)
• EPA Substance Registry System: Methyl 2,3,4-Tris-O-(phenylmethyl)-6,8-dideoxy-7,6-<2-(N,N-dimethylamino)-1-oxa-3-azaprop-2-eno>-1-thio-D-erythro-β-D-galacto-octopyranoside(124915-83-9)

Safety Data

• Hazardous Substances Data: 124915-83-9(Hazardous Substances Data)

Upstream product

• 3908-55-2 Trimethyl(methylthio)silane 
• 124780-59-2 1-O-Acetyl-2,3,4-tris-O-(phenylmethyl)-6,8-dideoxy-7,6-<2-(N,N-dimethylamino)-1-oxa-3-azaprop-2-eno>-D-erythro-α-D-galacto-octopyranose 
• 124780-66-1 methyl (E)-2,3-di-O-benzyl-6,7,8-trideoxy-α-D-galacto-oct-6-enopyranoside 
• 124780-55-8 (2S,3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-((2R,3R)-3-methyl-oxiranyl)-tetrahydro-pyran-3-ol 
• 124780-56-9 Methyl 2,3-Bis-O-(phenylmethyl)-6,8-dideoxy-7,6-<2-(N,N-dimethylamino)-1-oxa-3-azaprop-2-eno>-D-erythro-α-D-galacto-octopyranoside 
• 124780-54-7 methyl (E)-4-O-benzoyl-2,3-di-O-benzyl-6,7,8-trideoxy-α-D-galacto-oct-6-enoside 
• 124780-57-0 Methyl 2,3,4-Tris-O-(phenylmethyl)-6,8-dideoxy-7,6-<2-(N,N-dimethylamino)-1-oxa-3-azaprop-2-eno>-D-erythro-α-D-galacto-octopyranoside 
• 100-39-0 benzyl bromide 

Downstream Products

• 124780-59-2 1-O-Acetyl-2,3,4-tris-O-(phenylmethyl)-6,8-dideoxy-7,6-<2-(N,N-dimethylamino)-1-oxa-3-azaprop-2-eno>-D-erythro-α-D-galacto-octopyranose 

Relevant articles and documents

Stereocontrolled lincomycin synthesis

The synthesis from methyl α-D-galactopyranoside (6) of methyl thiolincosaminide (2), the direct synthetic precursor to lincomycin (1), is presented. The key step for controlling the off-pyranose stereocenters C-6 and C-7 is a novel intramolecular nitrogen delivery reaction using epoxy alcohol 10. Reaction of 10 with dimethylcyanamide in the presence of sodium hydride and imidazole leads to the oxazoline 14, a protected vicinal amino alcohol. The synthesis is completed by efficient exchange of acetal for thioacetal, followed by hydrolysis of the oxazoline and removal of the benzyl groups. The target 2 is obtained in 22 steps and 28% overall yield from 6.