264218-65-7

Basic information

• Product Name: (1R,1'S,5R,8aR)-N-benzyl-2-[3-oxo-1-((1'-phenylmethoxy)hexane)-1,5,6,8a-tetrahydro-oxazolo[3,4-a]pyridin-5-yl]-N-4-hydroxy-butyl acetamide
• Synonyms: (1R,1'S,5R,8aR)-N-benzyl-2-[3-oxo-1-((1'-phenylmethoxy)hexane)-1,5,6,8a-tetrahydro-oxazolo[3,4-a]pyridin-5-yl]-N-4-hydroxy-butyl acetamide
• CAS NO: 264218-65-7
• Molecular Weight: 548.723
• Mol File: 264218-65-7.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (1R,1'S,5R,8aR)-N-benzyl-2-[3-oxo-1-((1'-phenylmethoxy)hexane)-1,5,6,8a-tetrahydro-oxazolo[3,4-a]pyridin-5-yl]-N-4-hydroxy-butyl acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,1'S,5R,8aR)-N-benzyl-2-[3-oxo-1-((1'-phenylmethoxy)hexane)-1,5,6,8a-tetrahydro-oxazolo[3,4-a]pyridin-5-yl]-N-4-hydroxy-butyl acetamide(264218-65-7)
• EPA Substance Registry System: (1R,1'S,5R,8aR)-N-benzyl-2-[3-oxo-1-((1'-phenylmethoxy)hexane)-1,5,6,8a-tetrahydro-oxazolo[3,4-a]pyridin-5-yl]-N-4-hydroxy-butyl acetamide(264218-65-7)

Safety Data

• Hazardous Substances Data: 264218-65-7(Hazardous Substances Data)

Upstream product

• 708197-74-4 [(1R,5R,7S,8R,8aS)-1-((S)-1-Benzyloxy-hexyl)-7-(imidazole-1-carbothioyloxy)-3-oxo-8-phenylselanyl-hexahydro-oxazolo[3,4-a]pyridin-5-yl]-acetic acid methyl ester 
• 708197-73-3 [(1R,5R,7R,8S,8aS)-1-((S)-1-Benzyloxy-hexyl)-7-(imidazole-1-carbothioyloxy)-3-oxo-8-phenylselanyl-hexahydro-oxazolo[3,4-a]pyridin-5-yl]-acetic acid methyl ester 
• 708197-78-8 [(1R,1'S,5R,9R)-3-oxo-1-((1'-phenylmethoxy)hexyl)-1,5,6,8a-tetrahydrooxazolo[3,4-a]pyridin-5-yl]acetic acid 
• 264218-60-2 [(1R,5R,7S,8R,8aS)-1-((S)-1-Benzyloxy-hexyl)-7-hydroxy-3-oxo-8-phenylselanyl-hexahydro-oxazolo[3,4-a]pyridin-5-yl]-acetic acid methyl ester 
• 264218-58-8 [(1R,5R,7R,8S,8aS)-1-((S)-1-Benzyloxy-hexyl)-7-hydroxy-3-oxo-8-phenylselanyl-hexahydro-oxazolo[3,4-a]pyridin-5-yl]-acetic acid methyl ester 
• 59578-63-1 4-(benzylamino)-1-butanol 
• 1054655-93-4 [(1R,1'S,5R,9R)-3-oxo-1-((1'-phenylmethoxy)hexyl)-1,5,6,8a-tetrahydrooxazolo[3,4-a]pyridin-5-yl]acetic acid chloride 

Downstream Products

• 264218-71-5 (1'R,2R,2'S,6R)-N-benzyl-2-{6-(2'-phenylmethoxy-1'-hydroxy-heptyl)-1-[3-(toluene-4-sulfonylamino)-propyl]-1,2,3,6-tetrahydro-pyridin-2-yl}-N-(4-hydroxy-butyl)-acetamide 
• 264218-73-7 (1'R,2R,2'S,6R)-methanesulfonic acid 4-[benzyl-({6-(2'-phenylmethoxy-1'-hydroxy-heptyl)-1-[3-(toluene-4-sulfonylamino)-propyl]-1,2,3,6-tetrahydro-pyridin-2-yl}-acetyl)-amino]-butyl ester 
• 264218-67-9 (1'R,2R,2'S,6R)-N-benzyl-2-[6-(2'-phenylmethoxy-1'-hydroxy-heptyl)-1,2,3,6-tetrahydro-pyridin-2-yl]-N-(4-hydroxy-butyl)-acetamide 

Relevant articles and documents

Asymmetric total synthesis of (+)-cannabisativine

The asymmetric total synthesis of natural (+)-cannabisativine 1 was completed in 19 steps and 7% overall yield. The key synthetic intermediate 29 was prepared with a high degree of stereocontrol in 12 steps starting from chiral 1-acylpyridinium salt 10. Addition of zinc enolate 11 to pyridinium salt 10 furnished dihydropyridone 12 containing two contiguous stereocenters of the correct absolute configuration. Luche reduction of ketone 16 afforded diol 17 in high yield (96%) and excellent diastereoselectivity. The Mukaiyama-Michael reaction of pyridones 27a/b with O-silyl ketene acetal 32 gave phenyl selenyl ketones 33a/b with complete stereoselectivity. Elimination of cis-β-hydroxyselenides 34 and 35 effected the regiocontrolled preparation of tetrahydropyridine derivative 29. Several approaches to the macrocyclic ring closure of the 13-membered ring were investigated, ultimately leading to the completion of an asymmetric synthesis of the target compound with a high degree of stereocontrol.