96154-47-1

Basic information

• Product Name: 1-Butanol, 2-methyl-4-(phenylmethoxy)-, (2R)-
• CAS NO: 96154-47-1
• Molecular Formula: C12H18O2
• Molecular Weight: 194.274
• Mol File: 96154-47-1.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: 1-Butanol, 2-methyl-4-(phenylmethoxy)-, (2R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Butanol, 2-methyl-4-(phenylmethoxy)-, (2R)-(96154-47-1)
• EPA Substance Registry System: 1-Butanol, 2-methyl-4-(phenylmethoxy)-, (2R)-(96154-47-1)

Safety Data

• Hazardous Substances Data: 96154-47-1(Hazardous Substances Data)

Upstream product

• 389086-15-1 (4R)-4-benzyl-3-(4-benzyloxy-1-oxobutyl)-2-oxazolidinone 
• 1458033-17-4 (R)-4-benzyl-3-((R)-4-(benzyloxy)-2-methylbutanoyl) oxazolidin-2-one 
• 4541-14-4 4-benzyloxy-butan-1-ol 
• 100-39-0 benzyl bromide 
• 10385-30-5 4-(benzyloxy)butanoic acid 
• 100-44-7 benzyl chloride 
• 154912-69-3 (2R)-1-(tert-butyldiphenylsilyloxy)-2-methyl-4-benzoxybutane 
• 154912-70-6 (3R)-4-{[tert-butyl(diphenyl)silyl]oxy}-3-methylbutan-1-ol 
• 186641-79-2 (R)-4-((tert-Butyldiphenylsilyl)oxy)-3-methylbutanal 
• 186641-76-9 (2R)-1-(tert-butyldiphenylsilyloxy)-3-cyano-2-methylpropane 
• 100-51-6 benzyl alcohol 
• 1393834-11-1 (2'R,4R)-3-(4'-benzyloxy-2'-methylbutanoyl)-4,5,5-triphenyloxazolidinone 
• 363165-99-5 4-(benzyloxyl)-but-2-enoic acid 
• 887706-33-4 C₁₄H₂₂O₃ 

Downstream Products

• 91550-14-0 (2R)-4-(Benzyloxy)-2-methyl-1-butanal 
• 154912-76-2 (2R,5S,7S)-8-Benzyloxy-2-methyl-octane-1,5,7-triol 
• 154912-77-3 (R)-4-((4S,6S)-6-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-2-methyl-butan-1-ol 
• 154912-78-4 (R)-4-((4S,6S)-6-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-2-methyl-butyraldehyde 
• 154912-67-1 ((R)-4-Bromo-2-methyl-butoxy)-tert-butyl-diphenyl-silane 
• 154912-70-6 (3R)-4-{[tert-butyl(diphenyl)silyl]oxy}-3-methylbutan-1-ol 
• 154912-71-7 Methanesulfonic acid (R)-4-(tert-butyl-diphenyl-silanyloxy)-3-methyl-butyl ester 
• 154912-72-8 (2S,7R)-1-Benzyloxy-8-(tert-butyl-diphenyl-silanyloxy)-7-methyl-oct-3-yn-2-ol 
• 154912-73-9 (Z)-(2S,7R)-1-Benzyloxy-8-(tert-butyl-diphenyl-silanyloxy)-7-methyl-oct-3-en-2-ol 
• 154912-75-1 (2S,4S,7R)-1-Benzyloxy-8-(tert-butyl-diphenyl-silanyloxy)-7-methyl-octane-2,4-diol 
• 1054618-19-7 (S)-1-[(R)-6-((4S,6S)-6-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-3-hydroxy-4-methyl-hexanoyl]-piperidine-2-carboxylic acid methyl ester 
• 154912-80-8 (S)-1-[(R)-6-((4S,6S)-6-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-4-methyl-2,3-dioxo-hexanoyl]-piperidine-2-carboxylic acid methyl ester 
• 154912-74-0 (R)-2-Benzyloxy-1-{(2R,3S)-3-[(R)-4-(tert-butyl-diphenyl-silanyloxy)-3-methyl-butyl]-oxiranyl}-ethanol 
• 1443232-98-1 5-[(2R)-4-benzoxy-2-methylbutylsulfanyl]-1-phenyl-1H-tetrazole 

Relevant articles and documents

A Novel Synthesis of Sex Pheromone from the Longicorn Beetle (Psacothea hilaris)

Abstract: An asymmetric synthesis of (8Z,21R)-21-methylpentatriacont-8-ene, the sex pheromoneof the yellow-spotted longicorn beetle Psacotheahilaris, has been achieved using Evan’s induction as the keystep. Based on the asymmetric methylation product of chiral (R)-4-benzyl-1,3-oxazolidin-2-one, the carbon chainof the target molecule was assembled through aC5+C12+C11+C8sequence. (2R)-4-(Benzyloxy)-2-methylbutan-1-ol, which can be obtained fromγ-lactone following Evan’s protocol, was connected to aC12 alkyl group. The chiral methyl group remained thekey moiety (97% ee). After another Wittigreaction and catalytic hydrogenation step, the designed key intermediate(13R)-13-methylheptacosan-1-ol wasobtained. Finally, after oxidation and Wittig reaction, the synthesis of thetarget molecule was completed in 10 linear steps with an ultra-high overallyield of 36.2%.

Syn-effect' in the diastereoselective alkylation of 3-[(E)-α,β-unsaturated-γ-substituted]-N-acyloxazolidinones

Synthetic methods for the formation of alkenes usually produce the E-alkene because it is more stable. However, in isomerization reaction (double bond migration) that takes place in α, β-unsaturated carbonyl compounds, when these carbonyl compounds are exposed to strong bases, furnish Z-alkenes highly stereoselective depending on the γ-substituent in the α, β-unsaturated carbonyl. This stereoselectivity can be attributed to the known Syn-effect. The synthetic value of this methodology is the achievement of chiral alcohol bearing an electron rich Z-alkene, as well as substituted, which was accomplished via removal of the oxazolidinone moiety under treatment with NaBH4, THF-H2O.

Highly stereocontrolled total synthesis of β-d-mannosyl phosphomycoketide: A natural product from mycobacterium tuberculosis

β-d-Mannosyl phosphomycoketide (C32-MPM), a naturally occurring glycolipid found in the cell walls of Mycobacterium tuberculosis, acts as a potent antigen to activate T-cells upon presentation by CD1c protein. The lipid portion of C32-MPM contains a C32-mycoketide, consisting of a saturated oligoisoprenoid chain with five chiral methyl branches. Here we develop several stereocontrolled approaches to assemble the oligoisoprenoid chain with high stereopurity (>96%) using Julia-Kocienski olefinations followed by diimide reduction. By careful choice of olefination sites, we could derive all chirality from a single commercial compound, methyl (2S)-3-hydroxy-2-methylpropionate (>99% ee). Our approach is the first highly stereocontrolled method to prepare C32-MPM molecule with >96% stereopurity from a single >99% ee starting material. We anticipate that our methods will facilitate the highly stereocontrolled synthesis of a variety of other natural products containing chiral oligoisoprenoid-like chains, including vitamins, phytol, insect pheromones, and archaeal lipids.