627091-58-1

Basic information

• Product Name: (α'S,2S)-2-(3'-benzyloxy-α'-methylbenzyloxy)propanal
• Synonyms: (α'S,2S)-2-(3'-benzyloxy-α'-methylbenzyloxy)propanal
• CAS NO: 627091-58-1
• Molecular Weight: 284.355
• Mol File: 627091-58-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (α'S,2S)-2-(3'-benzyloxy-α'-methylbenzyloxy)propanal(CAS DataBase Reference)
• NIST Chemistry Reference: (α'S,2S)-2-(3'-benzyloxy-α'-methylbenzyloxy)propanal(627091-58-1)
• EPA Substance Registry System: (α'S,2S)-2-(3'-benzyloxy-α'-methylbenzyloxy)propanal(627091-58-1)

Safety Data

• Hazardous Substances Data: 627091-58-1(Hazardous Substances Data)

Upstream product

• 320727-36-4 1-(3'-benzyloxyphenyl)ethanol 
• 100-39-0 benzyl bromide 
• 121-71-1 3-Hydroxyacetophenone 
• 34068-01-4 1-[3-(phenylmethoxy)phenyl]ethan-1-one 
• 627091-54-7 3'-benzyloxy-α'-methylbenzyl 2,2,2-trichloroethanimidate 
• 627091-55-8 ethyl (2S)-2-(3'-benzyloxy-α'-methylbenzyloxy)propanoate 
• 627091-56-9 (α'S,2S)-2-(3'-benzyloxy-α'-methylbenzyloxy)propan-1-ol 

Downstream Products

• 627091-56-9 (α'S,2S)-2-(3'-benzyloxy-α'-methylbenzyloxy)propan-1-ol 
• 627091-66-1 (α'S,2S)-2-(3'-hydroxy-α'-methylbenzyloxy)propanal 

Relevant articles and documents

Regioselectivity in the syntheses of enantiopure 2-benzopyrans through intramolecular cyclization of tethered lactaldehydes. Conformations of the products

Using titanium tetraisopropoxide, the enantiopure tethered lactaldehyde (α′S,2S)-2-(3′-hydroxy-α′-methyl-benzyloxy) propanal (6) is cyclized with complete regio- and diastereoselectivity ortho to the phenolic hydroxyl group to give (1S,3S,4R)-3,4-dihydro-1,3,-dimethyl-2-benzopyran-4,5-diol (7). Similar cyclization of the epimeric (α′R,2S)-lactaldehyde (25) yields solely the corresponding (1R,3S,4R)-4,5-diol (34). The 4,5-diacetate (26), but not (35), undergoes conformational inversion of the heterocyclic ring through significant 4,5-peri interactions between the adjacent acetoxy substituents. Spontaneous cyclizations of the corresponding phenoxide ions of the lactaldehydes (6) and (25), generated by fluoride from their silyl ethers, led to the related 4,7-diols with high regioselectivity through ring-closure para to the aromatic oxygen.