116183-49-4

Basic information

• Product Name: (2R,3S)-3-phenyl-butane-1,2-diol
• Synonyms: (2R,3S)-3-phenyl-butane-1,2-diol
• CAS NO: 116183-49-4
• Molecular Weight: 166.22
• Mol File: 116183-49-4.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: (2R,3S)-3-phenyl-butane-1,2-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S)-3-phenyl-butane-1,2-diol(116183-49-4)
• EPA Substance Registry System: (2R,3S)-3-phenyl-butane-1,2-diol(116183-49-4)

Safety Data

• Hazardous Substances Data: 116183-49-4(Hazardous Substances Data)

Upstream product

• 21915-53-7 cis-2,3-epoxy-3-phenyl-1-propanol 
• 352287-96-8 (E)-3-(4-bromophenyl)but-2-enoic acid ethyl ester 
• 883892-28-2 (E)-ethyl 3-(3-bromophenyl)but-2-enoate 
• 1065168-98-0 (E)-3-(3-bromophenyl)-but-2-en-1-ol 
• 352287-97-9 (E)-3-(4-bromo-phenyl)-but-2-en-1-ol 
• 75-24-1 trimethylaluminum 
• 50-00-0 formaldehyd 
• 34713-70-7 2-Phenylpropanal 
• 40641-81-4 trans-2,3-epoxy-3-phenylpropan-1-ol 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 104196-23-8 (2S,3S)-2,3-epoxy-3-phenyl-1-propanol 
• 98-86-2 acetophenone 
• 54976-38-4 (E)-3-phenylbut-2-en-1-ol 
• 945-93-7 ethyl (E)-3-phenylbut-2-enoate 

Downstream Products

• 7782-24-3 (S)-2-Phenylpropionic acid 

Relevant articles and documents

Synthesis and Structure-Activity Relationship Studies of C2-Modified Analogs of the Antimycobacterial Natural Product Pyridomycin

A series of derivatives of the antimycobacterial natural product pyridomycin have been prepared with the C2 side chain attached to the macrocyclic core structure by a C-C single bond, in place of the synthetically more demanding enol ester double bond found in the natural product. Hydrophobic C2 substituents of sufficient size generally provide for potent anti-Mtb activity of these dihydropyridomycins (minimum inhibitory concentration (MIC) values around 2.5 μM), with several analogs thus approaching the activity of natural pyridomycin. Surprisingly, some of these compounds, in contrast to pyridomycin, are insensitive to overexpression of InhA in Mycobacterium tuberculosis (Mtb). This indicates that their anti-Mtb activity does not critically depend on the inhibition of InhA and that their overall mode of action may differ from that of the original natural product lead.

[1,2]-Wittig rearrangement of (benzyloxy)acetamides

[1,2]-Wittig rearrangement of (benzyloxy)acetamides can lead to substituted α-hydroxyamides in good yields and good diastereoselectivity. Georg Thieme Verlag Stuttgart.

Experimental and theoretical studies of the internal stereodifferentiation occurring during the lithiation of β-stereogenic alkyl carbamates. Kinetic resolutions by (-)-sparteine-mediated deprotonation

The deprotonation of β-stereogenic alkyl carbamates 8 with sec-butyllithium/TMEDA proceeds kinetically controlled with differentiation between the diastereotopic protons at the α-methylene group. The lithium intermediates 9A and 9B are trapped by electrophiles to give carboxylic acid esters 10A/ B and stannanes 11A/B, 13A/B. The diastereomeric ratio of A to B is independent of the electrophile. The highest efficiency is achieved with β-aryl-β-alkyl-substituted starting compounds 8d-f. The trends in the experimentally observed diastereoselectivities are reflected by the results of semiempirical PM3 calculations on the transition states of the deprotonation reaction. - As a result of double stereodifferentiation, application of the chiral base sec-butyllithium/(-)-sparteine gives rise to efficient kinetic resolution of racemic alkyl carbamates. VCH Verlagsgesellschaft mbH, 1996.