157117-17-4

Upstream product

• 6847-14-9 N-benzoyl-D-glucosamine 

Downstream Products

• 157117-18-5 Methanesulfonic acid (1R,2S)-2-benzoylamino-3-(tert-butyl-diphenyl-silanyloxy)-1-((2R,4S,5R)-5-methanesulfonyloxy-2-methyl-[1,3]dioxan-4-yl)-propyl ester 
• 220869-68-1 2-benzamido-2-deoxy-1-O-t-butyldiphenylsilyl-4,6-O-ethylidene-3-O-methylsulfonyl-D-glucitol 
• 157117-26-5 (1R,4'S,5'S)-1-<4'-(t-butyldiphenylsilyl)oxymethyl-2'-phenyl-4',5'-dihydrooxazol-5'-yl>pentadecan-1-ol 
• 220869-71-6 (4S,5S)-4-(t-butyldiphenylsilyl)oxymethyl-2-phenyl-4,5-dihydrooxazole-5-carbaldehyde 
• 220869-75-0 (1R,4'S,5'S)-1-<4'-hydroxymethyl-2'-phenyl-4',5'-dihydrooxazol-5'-yl>pentadecan-1-ol 
• 220869-70-5 (1R,2R,4'S,5'S)-1-<4'-(t-butyldiphenylsilyl)oxymethyl-2'-phenyl-4',5'-dihydrooxazol-5'-yl>propane-1,2,3-triol 
• 220869-79-4 (1R,4'S,5'S)-1-<4'-(2''-acetamido-3'',4'',6''-tri-O-acetyl-2''-deoxy-β-D-glucopyranosyl)oxymethyl-2'-phenyl-4',5'-dihydrooxazol-5'-yl>pentadecan-1-ol 
• 220869-77-2 (1R,4'S,5'S)-1-<4'-(3'',4'',6''-tri-O-acetyl-2''-chloroacetamido-2''-deoxy-β-D-glucopyranosyl)oxymethyl-2'-phenyl-4',5'-dihydrooxazol-5'-yl>pentadecan-1-ol 
• 220869-81-8 (2S,3S,4R)-1-O-(2''-acetamido-3'',4'',6''-tri-O-acetyl-2''-deoxy-β-D-glucopyranosyl)-3-O-benzoyl-2-hexadecanoylaminooctadecane-1,3,4-triol 
• 157117-22-1 Toluene-4-sulfonic acid (2S,3S)-3-[(4S,5S)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2-phenyl-4,5-dihydro-oxazol-5-yl]-oxiranylmethyl ester 
• 157117-19-6 Methanesulfonic acid (2R,4S,5R)-4-[(4S,5S)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2-phenyl-4,5-dihydro-oxazol-5-yl]-2-methyl-[1,3]dioxan-5-yl ester 
• 157117-23-2 (4S,5S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2-phenyl-5-((2R,3S)-3-tridecyl-oxiranyl)-4,5-dihydro-oxazole 
• 157117-20-9 Methanesulfonic acid (1R,2S)-2-[(4S,5S)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2-phenyl-4,5-dihydro-oxazol-5-yl]-2-hydroxy-1-hydroxymethyl-ethyl ester 
• 157117-30-1 N-[(1S,2S,3R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2,3-dihydroxy-heptadecyl]-benzamide 

Relevant academic research and scientific papers

Efficient stereocontrolled synthesis of D-erythro-sphingosine from N-benzoyl-D-glucosamine

D-erythro-Sphingosine is synthesized from N-benzoyl-D-glucosamine 2 in a highly regio- and stereo-controlled manner. The key features in the synthesis involve the efficient conversion of compound 2 into the vinyl epoxide 10 and the subsequent SN2′-type reaction with a Grignard reagent in the presence of CuCN to afford the 1-O,2-N-protected sphingosine 11.

Regio- and stereocontrolled synthesis ofD-erythrosphingosine and phytosphingosine fromDglucosamine

D-erythro-Sphingosine (1) and phytosphingosine (2) have been efficiently synthesized from D-glucosamine by utilizing its whole carbon skeleton and functional groups. In this synthetic route, regioselective alkylation of the epoxy-tosylate 9 was achieved with a copper(I)-catalyzed Grignard reagent to give the key intermediate 10, which was converted to both 1 and 2 via regioselective formation of the iodohydrin 11.