61866-19-1

Upstream product

• 3481-15-0 (S)-[α-D]-benzyl alcohol 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 4181-90-2 (R)-(α-2H)benzyl alcohol 
• 77944-67-3 (R-)-(-)-(η5-C5H5)Fe(CO)2CHDPh 
• 1315562-87-8 (R)-(-)-[1D₁]-S-benzyl O,O-diisopropyl thiophosphate 
• 1350973-25-9 p-methylphenyl 3-O-(R)-benzyl-α-d1-4,6-O-benzylidene-2-O-(4-methoxylbenzyl)-1-thio-α-D-mannopyranoside 
• 851895-45-9 methyl 4-O-(R)-benzyl-α-d1-2,3-di-O-benzyl-α-D-glucopyranoside 
• 1350973-20-4 methyl 4-O-(R)-benzyl-α-d1-2,3-di-O-benzyl-6-O-tert-butyldiphenylsilyl-α-D-glucopyranoside 
• 851895-47-1 methyl 6-O-(R)-benzyl-α-d1-2,3-di-O-benzyl-α-D-glucopyranoside 
• 1350973-23-7 methyl 6-O-(R)-benzyl-α-d1-2,3-di-O-benzyl-4-O-(2-naphthylmethyl)-α-D-glucopyranoside 
• 89789-26-4 C₉H₉⁽²⁾HO₂ 

Relevant academic research and scientific papers

Rearrangement of lithiated S-alkyl O,O-dialkyl thiophosphates: Scope and stereochemistry of the thiophosphate-mercaptophosphonate rearrangement

S-Alkyl O,O-dialkyl thiophosphates are prepared by alkylation of the triethylammonium salt of O,O-diisopropyl thiophosphoric acid. S-Benzyl thiophosphate was metallated at temperatures of ≥-45 °C by trityllithium and LiTMP (lithium 2,2,6,6-tetramethylpiperidide) and S-alkyl thiophosphates only by LiTMP to give dipole-stabilised carbanions which rearrange to α-mercaptophosphonates in yields of up to 45%. Metallation occurs with a high primary kinetic isotope effect (kH/kD up to ≈50). When the lithium (R)-N-isopropyl-1-phenylethylamide was used to induce the isomerisation of S-pentyl thiophosphate an α-mercaptophosphonate with an ee of 22% was isolated. (R)-S-[1-D1]hexyl O,O-diisopropyl thiophosphate was rearranged to a dextrorotary α-mercapto-[1-D 1]hexylphosphonate, whose (R)-configuration was determined by chemical correlation. The thiophosphate-mercaptophosphonate rearrangement proceeds with retention of configuration. The Royal Society of Chemistry 2011.

Stereochemistry of the Ethanolamine Ammonia Lyase Reaction with Stereospecifically Labeled 1>-2-Aminoethanol

The antipodes of 1>-2-aminoethanol (10) have been synthesized from (S)-1>benzyl alcohol and separately subjected to the action of ethanolamine ammonia lyase in the presence of alcohol dehydrogenase, in order to determine whether the migration of a hydrogen atom from C-1 to C-2 during acetaldehyde formation is stereospecific. (R)-10 reacts 4 times as fast as (S)-10, the isotope effect showing that the pro-S hydrogen migrates preferentially in each case. 1H and 13C NMR spectra of the ethanol formed show that (R)-10 leads to CH3CHDOH while (S)-10 affords DCH2CH2OH, confirming the stereoselectivity of hydrogen transfer.