110744-89-3

Upstream product

• 87190-25-8 (S)-pinanediol {(benzyloxy)methyl}boronate 
• 74-95-3 1,1-dibromomethane 
• 18680-27-8 pinanediol 
• 7785-70-8 (+)-α-pinene 
• 15082-42-5 lithium benzyloxide 

Downstream Products

• 125783-59-7 (1R)-(1-2H)-2,3-di-O-benzyl-sn-glycerol 
• 125783-57-5 (1S)-(1-2H)-2,3-di-O-benzyl-sn-glycerol 
• 110744-92-8 (S)-pinanediol {(1R)-1,2-bis(benzyloxy)ethyl}boronate 

Relevant academic research and scientific papers

A Modular Approach to the Asymmetric Synthesis of Cytisine

The asymmetric synthesis of (+)-and (-)-cytisine starts with Matteson homologations for the construction of a chiral C3-building block. Conversion of the C3-building block into a dihydropyridone is achieved by straightforward functional group interconversions and ring closing metathesis. After bromination, this central building block was diastereospecifically converted into cytisine in five steps.

Synthesis of asymmetrically deuterated glycerol and dibenzylglyceraldehyde via boronic esters

(S)-Pinanediol [(benzyloxy)methyl]boronate (1a) has been converted via an improved procedure to (S)-pinanediol (1R)-[1,2-bis(benzyloxy)ethyl]boronate (3a) (96% de), which with (dibromomethyl)lithium has yielded (S)-pinanediol (1S,2S)-[2,3-benzyloxy)-1-bro