76498-56-1

Basic information

• Product Name: 1,2-dideoxy-4,5:6,7-di-O-isopropylidene-β-D-arabinoglycero-4-octulopyranose
• Synonyms: 1,2-dideoxy-4,5:6,7-di-O-isopropylidene-β-D-arabinoglycero-4-octulopyranose
• CAS NO: 76498-56-1
• Molecular Weight: 288.341
• Mol File: 76498-56-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1,2-dideoxy-4,5:6,7-di-O-isopropylidene-β-D-arabinoglycero-4-octulopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-dideoxy-4,5:6,7-di-O-isopropylidene-β-D-arabinoglycero-4-octulopyranose(76498-56-1)
• EPA Substance Registry System: 1,2-dideoxy-4,5:6,7-di-O-isopropylidene-β-D-arabinoglycero-4-octulopyranose(76498-56-1)

Safety Data

• Hazardous Substances Data: 76498-56-1(Hazardous Substances Data)

Upstream product

• 32786-02-0 2,3:4,5-bis-O-(isopropylidene)-D-fructopyranose aldehyde 
• 925-90-6 ethylmagnesium bromide 

Downstream Products

• 72581-18-1 (2S,3S)-3-Hydroxy-2-methyl-3-phenyl-1-((3aR,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-3a-yl)-propan-1-one 
• 72519-59-6 (2R,3R)-3-Hydroxy-2-methyl-3-phenyl-1-((3aR,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-3a-yl)-propan-1-one 

Relevant articles and documents

Stereochemistry of addition of carbanion reagents to 'diacetone fructose aldehyde'. Configurational assignment of a 1-deoxyheptulose derivative by X- ray crystallography and NMR studies directed to the assignment of isomeric adducts

The addition of carbanionic reagents to 'diacetone fructose aldehyde' (6) was investigated with a focus on the stereocontrol. The Grignard reagents, MeMgBr, EtMgBr, i-PrMgBr, and MeMgI, gave a high bias (≥90%) for one diastereomer, assigned as the R-isomer, in ether at -78 to 0°C. The reaction of PhMgBr showed diminished diastereoselectivity under these conditions, with a significant dependence of the isomer ratio on temperature and solvent. PhCH2MgBr only afforded the adduct of 'allylic rearrangement', namely 13, with poor diastereocontrol (ca. 60:40). MeLi, t-BuLi, PhLi, and LiCH2CO2-t-Bu provided adducts of 6 enriched in the R-isomer in the range of 80-89%, whereas 2-lithio-2-ethyl-1,3-dithiane gave a 94:6 ratio of R:S adducts (15a:15b). The R absolute stereochemistry at the carbinol C1 center of 4a was established through X-ray analysis of sulfamate derivative 2a. Carbon-13 NMR chemical shift criteria (the chemical shifts for C1 and C3) were identified to facilitate the stereochemical assignment of C1 adducts of 6.