948056-06-2

Basic information

• Product Name: N-(4S,5R)-benzyl-((2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)methylene)amine
• Synonyms: N-(4S,5R)-benzyl-((2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)methylene)amine
• CAS NO: 948056-06-2
• Molecular Weight: 245.321
• Mol File: 948056-06-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: N-(4S,5R)-benzyl-((2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)methylene)amine(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4S,5R)-benzyl-((2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)methylene)amine(948056-06-2)
• EPA Substance Registry System: N-(4S,5R)-benzyl-((2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)methylene)amine(948056-06-2)

Safety Data

• Hazardous Substances Data: 948056-06-2(Hazardous Substances Data)

Upstream product

• 155934-55-7 (4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolane-4-carbaldehyde 
• 100-46-9 benzylamine 
• 50600-40-3 (3aS,4S,6aR)-4-(iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole 

Downstream Products

• 301523-39-7 4-benzylamino-1,2,3,4,7,8-hexadeoxy-5,6-O-isopropylidene-D-ribo-oct-1,7-dienitol 
• 871676-63-0 1,2,4,7,8-pentadeoxy-3-benzoyl-4-(N-benzyl)acetamido-5,6-O-isopropylidene-D-allo-octa-1,7-dienitol 
• 871676-64-1 (1S,2S,3S,6R)-3-benzoyloxy-2-(N-benzyl)acetamido-8,8-dimethyl-7,9-dioxabicyclo[4.3.0]non-4-ene 
• 871676-65-2 1,2,4,7,8-pentadeoxy-3-benzoyl-4-benzylamino-5,6-O-isopropylidene-D-allo-octa-1,7-dienitol 
• 444883-30-1 (4S,5S,6R)-4-[(N-benzyl)amino]-5,6-(isopropylidenedioxy)-7-octen-1-yne 

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.

A concise synthetic route to the conduritols from pentoses

A short synthetic strategy for preparation of the conduritols is described. The key step employs a zinc-mediated fragmentation of protected methyl 5-deoxy-5-iodo-D-pentofuranosides followed by an allylation of the intermediate aldehyde in the same pot. Th