444883-30-1

Basic information

• Product Name: (4S,5S,6R)-4-[(N-benzyl)amino]-5,6-(isopropylidenedioxy)-7-octen-1-yne
• Synonyms: (4S,5S,6R)-4-[(N-benzyl)amino]-5,6-(isopropylidenedioxy)-7-octen-1-yne
• CAS NO: 444883-30-1
• Molecular Weight: 285.386
• Mol File: 444883-30-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (4S,5S,6R)-4-[(N-benzyl)amino]-5,6-(isopropylidenedioxy)-7-octen-1-yne(CAS DataBase Reference)
• NIST Chemistry Reference: (4S,5S,6R)-4-[(N-benzyl)amino]-5,6-(isopropylidenedioxy)-7-octen-1-yne(444883-30-1)
• EPA Substance Registry System: (4S,5S,6R)-4-[(N-benzyl)amino]-5,6-(isopropylidenedioxy)-7-octen-1-yne(444883-30-1)

Safety Data

• Hazardous Substances Data: 444883-30-1(Hazardous Substances Data)

Upstream product

• 106-96-7 propargyl bromide 
• 100-46-9 benzylamine 
• 444883-29-8 (4S,6S)-6-[(triethylsilyl)oxy]-7-octen-1-yn-4-ol 
• 948056-06-2 N-(4S,5R)-benzyl-((2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)methylene)amine 
• 155934-55-7 (4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolane-4-carbaldehyde 

Downstream Products

• 301523-39-7 4-benzylamino-1,2,3,4,7,8-hexadeoxy-5,6-O-isopropylidene-D-ribo-oct-1,7-dienitol 

Relevant articles and documents

Carbohydrate carbocyclization by a zinc-mediated tandem reaction and ring-closing enyne metathesis

Methyl 5-deoxy-5-iodo-pentofuranosides are reductively ring-opened and propargylated in a tandem fashion in the presence of zinc. The 1,7-enynes thus obtained are subjected to ring-closing enyne metathesis with catalyst B to produce functionalized 1-vinyl cyclohexenes. By adding BnNH2 to the tandem reaction, an amino group can be introduced in the 1,7-enyne products. Addition of 2-TMS-ethynylcerium(III) chloride after the reductive ring-opening produces the corresponding 1,6-enynes. Further annulation of the product 1,3-dienes can be achieved through a Diels - Alder reaction with good control of stereochemistry. These procedures constitute efficient methods for rapid carbocyclization and annulation of carbohydrates to produce a variety of functionalized five- and six-membered ring systems.