133316-59-3

Upstream product

• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 17985-72-7 1,2-bis(dimethylsilyl)benzene 
• 583-53-9 2,3-dibromobenzene 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 139215-45-5 1,2-bis(bromodimethylsilyl)benzene 

Downstream Products

• 123410-44-6 (1S,2S)-2-Amino-1,3-diphenyl-propan-1-ol 
• 111138-88-6 (1R,2S)-2-amino-1,3-diphenyl-1-propanol 

Relevant academic research and scientific papers

N-bis-silylation of α-amino acids: "benzostabases" as amino protecting group

N-Bis-trimethylsilylation of α-amino acids using the powerful trimethylsilyl triflate reagent is difficult, and is rendered impossible in the case of bulky side-chains (valine). However, favorable entropy changes resulting from a cyclization reaction allow the formation of "benzostabase" N-diprotections regardless of the side-chain bulk.

The "benzostabase" protecting group for primary amines; application to aliphatic amines

The "benzostabase" (BSB) protecting group has been applied to primary aliphatic amines. It can be introduced via a dehydrogenative silylation employing an air- and moisture-stable reagent, and is appreciably more acid-stable than the related "stabase" group. BSB protection has been used in a stereoselective synthesis of amino-alcohols involving the addition of organometallic reagents to protected amino-aldehydes under "non-chelation control".