195006-97-4

Upstream product

• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 
• 211567-26-9 Methanesulfonic acid (2R,4aR,6R,7R,8R,8aR)-7-acetylamino-6-dodecyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester 
• 211567-22-5 dodecyl 3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranoside 
• 147025-06-7 dodecyl 2-(acetylamino)-2-deoxy-β-D-glucopyranoside 
• 154564-64-4 dodecyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 100-52-7 benzaldehyde 
• 112-53-8 1-dodecyl alcohol 
• 434948-95-5 1-dodecyl (R)-4,6-O-benzylidene-2-deoxy-2-(trans-3-phenyl-2-propenamido)-β-D-allopyranoside 
• 434949-32-3 1-dodecyl 2-amino-(R)-4,6-O-benzylidene-2-deoxy-2-N-3-O-methylidene-2-N-(trans-3-phenyl-2-propenoyl)-β-D-allopyranoside 
• 434949-67-4 1-dodecyl 2-amino-(R)-4,6-O-benzylidene-2-deoxy-2-N-[(2S,3R)-2,3-epoxy-3-phenylpropanoyl]-2-N-3-O-methylidene-β-D-allopyranoside 
• 211567-29-2 1-dodecyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-allopyranoside 

Downstream Products

• 211567-35-0 Bis-(2-chloro-ethyl)-((3aR,4R,5aR,8R,9aR,9bS)-4-dodecyloxy-2-oxo-8-phenyl-octahydro-1,5,7,9-tetraoxa-3-aza-2λ⁵-phospha-cyclopenta[a]naphthalen-2-yl)-amine 
• 434948-95-5 1-dodecyl (R)-4,6-O-benzylidene-2-deoxy-2-(trans-3-phenyl-2-propenamido)-β-D-allopyranoside 
• 434949-32-3 1-dodecyl 2-amino-(R)-4,6-O-benzylidene-2-deoxy-2-N-3-O-methylidene-2-N-(trans-3-phenyl-2-propenoyl)-β-D-allopyranoside 
• 434949-67-4 1-dodecyl 2-amino-(R)-4,6-O-benzylidene-2-deoxy-2-N-[(2S,3R)-2,3-epoxy-3-phenylpropanoyl]-2-N-3-O-methylidene-β-D-allopyranoside 

Relevant academic research and scientific papers

Stereoselective synthesis of oxiranes using oxazolidines derived from 2-amino-2-deoxy-D-allose as chiral auxiliaries

The synthesis of 2,3-epoxyamide derivatives of 2-amino-2-deoxy-D-allose is described. Epoxidation of the corresponding α,β-unsaturated amides with m-CPBA took place with better stereoselectivity when an oxazolidine ring was fused to the 2,3-positions of the sugar molecule. In most cases, both stereoisomers could be isolated and characterized. The stereochemistry of the new stereogenic centers was then determined by cleavage of the oxirane moiety from the chiral auxiliary, which was also recovered.

Alkylating agents from sugars. Cyclophosphamides derived from 2-amino- 2-deoxy-D-allose

Cyclophosphamides derived from alkyl 2-amino-4,6-O-benzylidene-2-deoxy- β-D-allopyranosides have been synthesized with good yield by treatment of the corresponding 2-amino-2-deoxy-D-allose derivatives with bis(2- chloroethyl)phosphoramide dichloride. The ring-forming reaction took place with very high diastereoselectivity. Subsequent hydrogenolysis gave excellent yields of cyclophosphamides derived from alkyl 2-amino-2-deoxy-β-D- allopyranosides, with hydrophilicity greater than that of the precursors. The starting material was easily available from 2-acetamido-2-deoxy-D-glucose.