101864-30-6

Basic information

• Product Name: O⁴-benzoyl-O¹,O²;O⁵,O⁶-diisopropylidene-D-arabino-[3]hexulose
• Synonyms: O⁴-benzoyl-O¹,O²;O⁵,O⁶-diisopropylidene-D-arabino-[3]hexulose
• CAS NO: 101864-30-6
• Molecular Weight: 364.395
• Mol File: 101864-30-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: O⁴-benzoyl-O¹,O²;O⁵,O⁶-diisopropylidene-D-arabino-[3]hexulose(CAS DataBase Reference)
• NIST Chemistry Reference: O⁴-benzoyl-O¹,O²;O⁵,O⁶-diisopropylidene-D-arabino-[3]hexulose(101864-30-6)
• EPA Substance Registry System: O⁴-benzoyl-O¹,O²;O⁵,O⁶-diisopropylidene-D-arabino-[3]hexulose(101864-30-6)

Safety Data

• Hazardous Substances Data: 101864-30-6(Hazardous Substances Data)

Upstream product

• 98-88-4 benzoyl chloride 
• 189701-54-0 (R)-2-(tert-Butyl-diphenyl-silanyloxy)-1,2-bis-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanone 
• 51051-82-2 O³-benzoyl-O¹,O²;O⁵,O⁶-diisopropylidene-D-mannitol 
• 1707-77-3 1,2:5,6-di-O-isopropylidene-D-mannitol 
• 189701-88-0 (1S,2S)-2-(tert-Butyl-diphenyl-silanyloxy)-1,2-bis-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanol 
• 189701-50-6 (1R,2S)-2-(tert-Butyl-diphenyl-silanyloxy)-1,2-bis-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanol 

Downstream Products

• 189701-86-8 (1R,2R)-2-(2,6-Dichloro-benzyloxy)-1,2-bis-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanol 
• 189701-87-9 (S)-2-(2,6-Dichloro-benzyloxy)-1,2-bis-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanone 
• 51051-82-2 O³-benzoyl-O¹,O²;O⁵,O⁶-diisopropylidene-D-mannitol 
• 643-03-8 D-talitol 
• 170874-86-9 Methanesulfonic acid (1R,2S)-2-(tert-butyl-diphenyl-silanyloxy)-1,2-bis-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl ester 
• 170874-77-8 (2R,3R,4R,5R)-4-O-Benzoyl-1,2;5,6-di-O-isopropylidene-3-O-hexane-1,2,3,4,5,6-hexol 
• 170874-80-3 Benzoic acid (1S,3S)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-4-(toluene-4-sulfonyloxy)-butyl ester 
• 170874-78-9 (2R,3S,5S)-3-O-Benzoyl-1,2;5,6-di-O-isopropylidenehexane-1,2,3,5,6-pentol 
• 170874-79-0 (2R,3S,5S)-3-O-Benzoyl-1,2-O-isopropylidenehexane-1,2,3,5,6-pentol 
• 94869-54-2 3-O-Benzoyl-1,2;5,6-di-O-isopropyliden-4-O-methansulfonyl-D-mannitol 
• 189701-62-0 Benzoic acid (1R,2R)-1,2-bis-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-3-methyl-but-3-enyl ester 
• 100759-35-1 Mono-O-benzoyl-1,2;5,6-bis-O-isopropyliden-D-talit 
• 53735-99-2 1,2:5,6-di-O-isopropylidene-D-talo-hexitol 

Relevant articles and documents

Diastereoselective Grignard Additions to O-Protected Polyhydroxylated Ketones: A Reaction Controlled by Groundstate Conformation?

The O-protected polyhydroxy ketones 9-14 and 39, 42 add σ-type Grignard reagents with >90:10 stereoselectivity to give the 3,4-syn-adducts 17-22 and 43, 45, respectively, as the major diastereomers (Tables 1 and 2). The stereoselectivity is interpreted in terms of early transition states which are very close to the groundstate conformations shown in Figure 6 and 7. These demonstrate that the "top face" of the carbonyl group is much less shielded than the "bottom" face, Complexation phenomena are of minor importance. It is also shown that the classical transition state models (Felkin-Anh or chelate Cram) are not applicable to polyoxygenated ketones.