111137-99-6

Upstream product

• 1565-80-6 (2S)-2-methyl-1-butanol 
• 39637-99-5 (S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride 
• 20445-31-2 MTPA 
• 111070-64-5 (1R,3R,4S)-p-menthan-3-yl (2R)-2-hydroxymethylbutyrate 
• 601-75-2 ethylmalonic acid 
• 72447-52-0 (S)-2-Methyl-butyric acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 17257-71-5 (S)-Mosher acid 
• 122778-49-8 (S)-2-Chloromethyl-butyric acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 
• 111042-75-2 (1R,3R,4S)-p-menthan-3-yl hydrogen (R)-ethylmalonate 
• 154623-22-0 (E)-(2R,6R)-2-((1R,2S)-1-Hydroxy-2-methyl-butyl)-6-methyl-non-3-enedioic acid dimethyl ester 
• 20445-33-4 (R)-methoxytrifluoromethylphenylacetyl chloride 
• 137-32-6 (+/-)-2-methyl-1-butanol 

Relevant academic research and scientific papers

Assignment of the absolute configuration of β-chiral primary alcohols by NMR: Scope and limitations

The prediction of the absolute configuration of β-chiral primary alcohols from the 1H NMR spectra of their esters with (R)- and (S)- 9-anthrylmethoxyacetic acids (9-AMA, 3) is discussed. Low-temperature NM experiments, MM, semiempirical, ab initio, and aromatic shielding effect calculations allowed the identification of the main conformers and showed that, in all alcohols for which the calculated ΔE(ag) (CVff) is in the range of 0.7-1.5 kcal/mol, conformer a/a is the most stable. A simple model for the assignment of the absolute configuration from NMR data is presented and its reliability corroborated with alcohols (8-20) of known configuration. Nevertheless, cyclic alcohols 21-23 have much higher ΔE(ag) values (2.2-3.1 kcal/mol) due to their different conformational composition, and their absolute configuration cannot be reliably predicted by this method.

Predator - Prey Relationship between Navanax inermis and Bulla gouldiana : a Chemical Approach

Two new compounds, 5,6-dehydroaglajne-3 (9) and isopulo'upone (10), have been isolated and characterized, along with the already known niuhinone-B (7), from Navanax inermis and its prey Bulla gouldiana, firmly establishing on a chemical basis the predator - prey relationship between this pair of cephalaspidean opisthobranchs.The peculiarity of the metabolites and their structural analogy with other compounds isolated from other cephalaspidean molluscs assign a taxonomic relevance for them. Key words: Navanax inermis; Bulla gouldiana; cephalaspidean molluscs; polypropionates.

Application of modified Mosher's method for primary alcohols with a methyl group at C2 position.

The absolute configurations of a series of primary alcohols possessing a branched methyl group at C2 position were examined on the basis of a modified Mosher's method proposed by Minale et al. It was revealed that in many cases the absolute configurations

Nonreductive enantioselective ring opening of N-(methylsulfonyl)dicarboximides with diisopropoxytitanium α,α,α′,α′-tetraaryl-1,3-dioxolane-4,5- dimethanolate

The bicyclic and tricyclic meso-N-(methylsulfonyl)dicarboximides 1a-f are converted enantioselectively to isopropyl [(sulfonamido)carbonyl]-carboxylates 2a-f by diisopropoxytitanium TADDOLate (75-92% yield; see Scheme 3). The enantiomer ratios of the products are between 86:14 and 97:3, and recrystallization from CH2Cl2/hexane leads to enantiomerically pure sulfonamido esters 2 (Scheme 3). The enantioselectivity shows a linear relationship with the enantiomer excess of the TADDOL employed (Fig. 3). Reduction of the ester and carboxamide groups (LiAlH4) and additional reductive cleavage of the sulfonamido group (Red-Al) in the products 2 of imide-ring opening gives hydroxy-sulfonamides 3 and amino alcohols 4, respectively (Scheme 4). The absolute configuration of the sulfonamido esters 2 is determined by chemical correlation (with 2a, b; Scheme 6), by the X-ray analysis of the camphanate of 3e (Fig. I), and by comparative 19F-NMR analysis of the Mosher esters of the hydroxy-sulfonamides 3 (Table I). A general proposal for the assignment of the absolute configuration of primary alcohols and amines of Formula HXCH2CHR1R2, X = O, NH, is suggested (see 11 in Table I). It follows from the assignment of configuration of 2 that the Re carbonyl group of the original imide 1 is converted to an isopropyl ester group. This result is compatible with a rule previously put forward for the stereochemical course of reactions involving titanium TADDOLate activated chelating electrophiles (12 in Scheme 7). A tentative mechanistic model is proposed (13 and 14 in Scheme 7).

Structures and Stereochemistries of New Compounds Related to Alternaric Acid

Three alternaric acid-related compounds, viz., 10-deoxyalternaric acid 2, 10-deoxy-6,19-dihydroalternaric acid 3, and 10-deoxy-6,8,9,19-tetrahydroalternaric acid 4, have been isolated from Alternaria solani which is a causal fungus of early blight disease

Syntheses with Aliphatic Dialdehydes, XLIV. Chiral Pentamethine Cyanine Dyes and Heterocycles from Derivatives of (S)-(+)-2-sec-Butylmalonaldehyde

Syntheses and UV/Vis-spectroscopic properties of the chain-substituted, homochiral pentamethine cyanine dyes 16 and 17 are described. 16 and 17 as well as the homochiral five-, six-, and seven-membered heterocycles 11 - 15 are prepared from derivatives (5 and 6) of homochiral (S)-(+)-2-sec-Butylmalonaldehyde (8), the first known chiral malonaldehyde, which in turn is synthesized in a seven-step procedure from homochiral (S)-(-)-2-methyl-1-butanol (1).

Asymmetric Syntheses of Chiral Propane-1,3-diols Starting from Malonic Acid

Syntheses of chiral intermediates having one tertiary asymmetric centre were carried out via chiral half-esters of monoalkylmalonic acids.The menthyl half-ester of ethylmalonic acid afforded a single diastereoisomer through crystallisation-induced asymmetric transformation (second-order asymmertic transformation).Furthermore enantioselective preparation of unsymmertical propane-1,3-diol derivatives was achieved by the use of 8-phenylmenthyl half-esters.

Enantioselective Synthesis of Useful Chiral Precursors, Unsymmetrical Propane-1,3-diol Derivatives, from Malonic acid

Syntheses of chiral synthons via monosubstituted malonic chiral half esters were studied and chiral 3-silyloxy propanols were enantioselectively synthesised.