158570-83-3

Upstream product

• 136981-88-9 (Z)-1-(Methoxymethoxy)-3-(tri-n-butylstannyl)-1-butene 
• 158535-88-7 2,3-Di-O-benzyl-4-O-(tert-butyldimethylsilyl)-D-erythrose 
• 131433-65-3 (1R,2E)-1-(tri-n-butylstannyl)-1-(methoxymethoxy)-2-butene 
• 100-39-0 benzyl bromide 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 130412-79-2 (2R,3R)-2,3-bis(benzyloxy)-4-hydroxybutanoic acid 1,4-lactone 
• 158535-86-5 (2R,3R)-2,3-Bis(benzyloxy)-4-hydroxy-N-methoxy-N-methylbutanamide 
• 158535-87-6 (2R,3R)-2,3-Bis(benzyloxy)-4-<(tert-butyldimethylsilyl)oxy>-N-methoxy-N-methylbutanamide 

Relevant academic research and scientific papers

Stereoselective SE2′ additions of enantioenriched allylic tin and indium reagents to protected threose and erythrose aldehydes: A general strategy for the stereocontrolled synthesis of precursors to the eight diastereomeric hexoses and their enantiomers

The enantioenriched (～90-95% ee) α-alkoxy allylic stannanes (S)- and (R)-2.1 undergo in situ transmetallation with InCl3 in EtOAc and subsequent SE2′ addition to aldehydes to afford anti adducts 3.2a-d stereospecifically with excellent diastereoselectivity (90:10-98:2). Additions to the protected threose and erythrose aldehydes 4.2 and 4.4 are reagent controlled, yielding the anti adducts 5.1-5.4 with high stereoselectivity. These adducts are potential precursors of differentially protected L-talose, D-allose, L-glucose, and D-mannose.

Synthesis of Protected Carbohydrate Derivatives through Homologation of Threose and Erythrose Derivatives with Chiral γ-Alkoxy Allylic Stannanes

Additions of the γ-alkoxy allylic stannanes (S)-1 and (R)-1 and the racemate (RS)-1 to the threose and erythrose aldehyde derivatives 6 and 15 in the presence of BF3*OEt2 or MgBr2*OEt2 were examined in order to establish stereochemical preferences.It was found that (S)-1 and aldehyde 6 afforded the syn,anti,syn adduct 7 in the BF3-promoted reaction, while (R)-1 and 6 gave the syn,syn,syn adduct 8 under MgBr2 conditions.Likewise, (S)-1 and aldehyde 15 yielded the syn,anti,anti adduct 16 with BF3, whereas (R)-1 and 15 led to the syn,syn,anti adduct 17 with MgBr2.The MgBr2-promoted reactions showed sufficient rate differences between the matched and mismatched stannanes to allow the use of racemic stannane (RS)-1 in just over 2-fold excess, whereupon the matched adducts 8 and 17 were favored by greater than 9:1 over the mismatched adducts.The major adducts 7, 8, 16, and 17 were converted to the hexose derivatives 21, 30/31, 34, and 39 by ozonolysis, selective deprotection, and refunctionalization.Adducts 16 and 17 were dihydroxylated with OsO4-NMO to the deoxyoctose precursors 40/41 and 42/43.