124780-54-7

Upstream product

• 124780-66-1 methyl (E)-2,3-di-O-benzyl-6,7,8-trideoxy-α-D-galacto-oct-6-enopyranoside 
• 98-88-4 benzoyl chloride 

Downstream Products

• 124915-83-9 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 
• 124780-60-5 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-α-D-galacto-octopyranoside 
• 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 
• 124780-58-1 Methyl 6-Acetamido-7-O-acetyl-2,3,4-tris-O-(phenylmethyl)-6,8-dideoxy-D-erythro-α-D-galacto-octopyranoside 
• 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 
• 124820-33-3 N-[(1R,2R)-2-Hydroxy-1-((2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-methylsulfanyl-tetrahydro-pyran-2-yl)-propyl]-acetamide 
• 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 
• 14810-93-6 Methyl 6-Amino-6,8-dideoxy-1-thio-D-erythro-α-D-galacto-octopyranoside 
• 124780-55-8 (2S,3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-((2R,3R)-3-methyl-oxiranyl)-tetrahydro-pyran-3-ol 
• 124780-55-8 methyl 6,7-anhydro-2,3-di-O-benzyl-8-deoxy-α-D-threo-D-galacto-octopyranoside 
• 131751-03-6 methyl 6,7-anhydro-2,3-di-O-benzyl-4-O-(2-t-butoxycarbonylamino-2-phenylacetyl)-8-deoxy-α-D-threo-D-galacto-octoside 
• 131751-00-3 methyl 6,7-anhydro-2,3-di-O-benzyl-8-deoxy-4-O-(N-trichloroacetylcarbamoyl)-α-D-threo-D-galacto-octoside 
• 131750-95-3 Trichloro-acetic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-2-((2S,3R)-3-methyl-oxiranyl)-tetrahydro-pyran-3-yl ester 
• 131750-96-4 methyl 4,7-anhydro-2,3-di-O-benzyl-8-deoxy-β-L-erythro-D-galacto-octoside 

Relevant academic research and scientific papers

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.

Approaches to the Synthesis of Lincosamine, a Derived Portion of the Antibiotic Lincomycin

A variety of approaches towards the synthesis of lincosamine, a derived portion of the antibiotic lincomycin, are reported.Initial approaches involved the intramolecular delivery of a nitrogen atom (trichloroacetimidate, trichloroacetylcarbamate, carbamat