24347-56-6

Basic information

• Product Name: 1,2-Butanediol, 3-methyl-, (2S)-
• CAS NO: 24347-56-6
• Molecular Formula: C5H12O2
• Molecular Weight: 104.149
• Mol File: 24347-56-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 1,2-Butanediol, 3-methyl-, (2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Butanediol, 3-methyl-, (2S)-(24347-56-6)
• EPA Substance Registry System: 1,2-Butanediol, 3-methyl-, (2S)-(24347-56-6)

Safety Data

• Hazardous Substances Data: 24347-56-6(Hazardous Substances Data)

Upstream product

• 636580-98-8 (4S,1'R,2'S)-N-⁽³⁾-(1'-m-chlorobenzoyl-2'-hydroxy-3'-methyl-but-1'-yl)-4-phenyl-5,5-dimethyloxazolidin-2-one 

Downstream Products

• 188949-02-2 1α-[(tert-butyldimethylsilyl)oxy]-24R-[(methoxymethyl)oxy]-vitamin D₃ tert-butyldimethylsilyl ether 
• 57333-96-7 tacalcitol 
• 1173179-80-0 (S)-3-methylbutane-1,2-diyl bis(4-nitrobenzoate) 
• 79262-58-1 (R)-1,2-Bis-3-methylbutane 
• 90211-85-1 (24R)-6β-methoxy-22-phenylsulfonyl-24-hydroxy-3α,5α-cyclocholestane 
• 27460-26-0 24(R)-Hydroxycholesterol 
• 161029-82-9 (4S,5R,8R)-4-(tert-Butyl-dimethyl-silanyloxy)-8-[(E)-(1R,6R)-6-(tert-butyl-diphenyl-silanyloxy)-1,3,7-trimethyl-2-oxo-oct-3-enyl]-5-methyl-oxocan-2-one 
• 161029-80-7 C₂₇H₄₂OSi₂ 
• 161029-79-4 C₂₆H₃₈OSi₂ 
• 161029-81-8 ((E)-(R)-4-Bromo-1-isopropyl-pent-3-enyloxy)-tert-butyl-diphenyl-silane 
• 55123-01-8 (S)-(+)-1,2-epoxy-3-methylbutane 
• 79262-55-8 (S)-3-Methyl-1,2-butandiol-ditosylate 
• 90211-82-8 (2S)-1-tosyloxy-3-methylbutan-2-ol 
• 92572-90-2 (2R,4S)-4-Isopropyl-2-phenyl-[1,3]dioxolane 

Relevant articles and documents

Stereoselective functionalisation of SuperQuat enamides: asymmetric synthesis of homochiral 1,2-diols and α-benzyloxy carbonyl compounds

Homochiral (E)- and (Z)-enamides derived from SuperQuat (S)-4-phenyl-5,5-dimethyl-oxazolidin-2-one undergo highly diastereoselective epoxidation upon treatment with dimethyldioxirane. Subsequent epoxide opening with meta-chlorobenzoic acid proceeds via a stereoselective SN1-type process, with retention of configuration, to give the corresponding 1′-m-chlorobenzoyl-2′-hydroxy derivatives. Treatment of the SuperQuat enamides with mCPBA effects this two-step transformation in one pot. Reductive cleavage of the isolated 1′-m-chlorobenzoyl-2′-hydroxy derivatives (≥96% de) generates homochiral 1,2-diols in ≥96% ee. Alternatively, regioselective lithiation of the enamide at C(1′) with tBuLi followed by reaction with an aromatic aldehyde and in situ O-benzylation generates a 1′-(benzyloxy-aryl-methyl) substituted enamide with high diastereoselectivity. Subsequent oxidative cleavage of the enamide C{double bond, long}C bond with NaIO4/RuCl3 followed by methanolysis of the resultant N-acyl fragment furnishes an O-benzyl protected α-hydroxy methyl ester in high ee.