213686-90-9

Upstream product

• 213686-66-9 (5R,6S)-2-acetoxy-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazine 
• 762-72-1 allyl-trimethyl-silane 
• 105228-46-4 (5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one 

Downstream Products

• 216062-11-2 (2S,3R,6S)-6-[(R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-propyl]-2,3-diphenyl-morpholine-4-carboxylic acid benzyl ester 
• 216062-14-5 (2S,4S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-4-((R)-1,2-diphenyl-ethoxy)-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 216062-06-5 (1'R,3S)-1-tert-butyloxycarbonyl-3-(1',2'-diphenylethoxy)pyrrolidine 
• 213687-65-1 (2S,5R,6S)-2-(4-benzyloxycarbonyl-5,6-diphenyl-1,2,5,6-tetrahydro-4H-1,4-oxazin-2-yl)acetic acid 
• 216062-05-4 (2S,3R,6S)-6-(2-Hydroxy-ethyl)-2,3-diphenyl-morpholine-4-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

Asymmetric synthesis of (S)-(+)-carnitine and analogs

A general asymmetric route to enantiomerically pure (S)-(+)-carnitine and analogs has been investigated that involves mono-addition of organometallic reagents to the lactone carbonyl group of (5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin- 2-one and Lewis acid promoted stereoselective allylation of the resulting hemiacetals. The diastereomerically pure allyl oxazines thus obtained were readily converted into enantiomerically pure (S)-(+)-carnitine and two substituted analogs.

General asymmetric synthesis of hydroxymethylene and hydroxyethylene peptide isosteres

The Lewis acid-promoted coupling reactions of (5R, 6S)-2-acetoxy-4- (benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazines (11a-e, and 21), which are prepared easily from (+)-(5R, 6S)-4(benzyloxycarbonyl)- 5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (9), with allyltrimethylsilane proceeded to give the corresponding coupling products with moderate to excellent stereoselectivity in good yields. These coupling products (13a, b, and d) were converted to hydroxymethylene-(25a, b, and d) and hydroxyethylene (28) peptide isosteres.