296271-05-1

Basic information

• Product Name: (+)-(2R,4S)-4-[(1S,2R)-2,3-bis(benzyloxy)-1-hydroxypropyl]-2-(tert-butyl)-2-methyl-1,3-dioxan-5-one
• Synonyms: (+)-(2R,4S)-4-[(1S,2R)-2,3-bis(benzyloxy)-1-hydroxypropyl]-2-(tert-butyl)-2-methyl-1,3-dioxan-5-one
• CAS NO: 296271-05-1
• Molecular Weight: 442.552
• Mol File: 296271-05-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (+)-(2R,4S)-4-[(1S,2R)-2,3-bis(benzyloxy)-1-hydroxypropyl]-2-(tert-butyl)-2-methyl-1,3-dioxan-5-one(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(2R,4S)-4-[(1S,2R)-2,3-bis(benzyloxy)-1-hydroxypropyl]-2-(tert-butyl)-2-methyl-1,3-dioxan-5-one(296271-05-1)
• EPA Substance Registry System: (+)-(2R,4S)-4-[(1S,2R)-2,3-bis(benzyloxy)-1-hydroxypropyl]-2-(tert-butyl)-2-methyl-1,3-dioxan-5-one(296271-05-1)

Safety Data

• Hazardous Substances Data: 296271-05-1(Hazardous Substances Data)

Upstream product

• 20196-70-7 (+)-(R)-2,3-bis(benzyloxy)propanal 
• 170876-75-2 2-tert-butyl-2-methyl-1,3-dioxan-5-one 

Downstream Products

• 608-66-2 D-galactitol 
• 643-03-8 D-talitol 

Relevant articles and documents

Aldol Addition of Lithium and Boron Enolates of 1,3-Dioxan-5-ones to Aldehydes. A New Entry into Monosaccharide Derivatives

Methods allowing control of stereoselectivity in aldol reactions of enolates derived from 1,3-dioxan-5-ones (4) are described. Boron enolates, generated in situ, react with benzaldehyde to give the corresponding anti aldol selectively (the anti:syn ratio of up to 96:4) in high yield. Lithium enolates give high anti selectivity only with aldehydes branched at the α-position. Enantioselective deprotonation of CS symmetrical dioxanones (e.g., 4b) can be accomplished efficiently, with enantiomeric excess of up to 90%, with chiral lithium amide bases of general structure PhCH-(Me)N(Li)R (9, 10) if the R group is sufficiently bulky (e.g, R = adamantyl) or is fluorinated (e.g., R = CH2CF3). Dioxanone boron and lithium enolates react readily with glyceraldehyde derivatives (19), yielding protected ketohexoses (20 and 21).