42933-13-1

Usage

Uses

Used in Pharmaceutical Industry:
2-methylbutane-1,2,3,4,-tetrol is used as an intermediate in the synthesis of various pharmaceuticals for its unique chemical structure and properties that contribute to the development of new drugs.
Used in Cosmetic and Personal Care Products:
2-methylbutane-1,2,3,4,-tetrol is used as a component in cosmetic and personal care products due to its moisturizing and skin conditioning properties, enhancing the texture and feel of the products.
Used in Vitamin Synthesis:
2-methylbutane-1,2,3,4,-tetrol is used as a precursor in the synthesis of vitamin B2 (riboflavin), which plays a crucial role in the metabolism of carbohydrates and energy production in living organisms.
Used in Industrial Processes:
2-methylbutane-1,2,3,4,-tetrol is utilized in various industrial processes due to its unique chemical properties, contributing to the development of new materials and technologies.

InChI:InChI=1/C5H12O4/c1-5(9,3-7)4(8)2-6/h4,6-9H,2-3H2,1H3

Upstream product

• 583872-99-5 (6R,7R,15S)-15-[(S)-1-Hydroxy-2-(4-methoxy-benzyloxy)-ethyl]-15-methyl-1,8,13,16-tetraoxa-dispiro[5.0.5.4]hexadecan-14-one 
• 78-79-5 isoprene 
• 1375148-86-9 (2S,3R)-4-(4-methoxybenzyloxy)-3-methylbutane-1,2,3-triol 
• 1375148-77-8 (2S,3S)-ethyl 2,3-dihydroxy-4-(4-methoxybenzyloxy)-3-methylbutanoate 
• 1073561-30-4 C₁₁H₁₈O₇ 
• 1375148-84-7 (2S,3S)-4-(4-methoxybenzyloxy)-3-methylbutane-1,2,3-triol 
• 1375148-75-6 (2R,3S)-ethyl 2,3-dihydroxy-4-(4-methoxybenzyloxy)-3-methylbutanoate 
• 1013326-39-0 (E)-ethyl 4-(4-methoxybenzyloxy)-3-methylbut-2-enoate 
• 936335-24-9 (2R,3R)-dimethyl 2,3-dihydroxy-2-methylbutanedioate 
• 503473-27-6 (2S,3S)-4-(benzyloxy)-2-methylbutane-1,2,3-triol 
• 1375148-88-1 (2S,3R)-4-(4-methoxybenzyloxy)-3-methylbutane-1,2,3-triol 
• 1375148-78-9 (2R,3R)-ethyl 2,3-dihydroxy-4-(4-methoxybenzyloxy)-3-methylbutanoate 
• 936335-26-1 (2S,3R)-dimethyl 2,3-dihydroxy-2-methylbutanedioate 
• 617-54-9 citraconic acid dimethyl ester 

Downstream Products

• 93841-85-1 1,2,3,4-tetra-O-benzoyl-3-C-methylerythritol 
• 93836-33-0 1,2,3,4-tetra-O-benzoyl-3-C-methyl-L-threitol 

Relevant academic research and scientific papers

Synthesis of the ABCD fragment of gymnocin-B

A convergent synthesis of the ABCD fragment of gymnocin-B was accomplished. The tetracyclic ether ring system was synthesized by the construction of the BC ring system via the oxiranyl anion alkylation and ring expansion reaction, followed by the formation of the five-membered A-ring via a stereoselective radical cyclization reaction of a neopentyl-type iodide.

Concise asymmetric syntheses of the (+)-2-C-methyltetritol isomers

Two brief and facile syntheses of the title compounds have been developed using the diastereocontrolled addition of organometallics to a (R)-cyclohexylideneglyceraldehyde-derived ketone as the key steps. The addition of vinylmagnesium bromide to the ketone gave a 1:1 diastereomeric mixture of separable tertiary alcohols, which were converted to the target erythri- and threitols. On the other hand, the reaction of a dithianyl anion with the ketone gave only the single stereoisomer of a tertiary alcohol, which was converted to erythritol.

Phytochemical characterization and biological activity of secondary metabolites from three Limonium species

The comparative phytochemical constituents of three Limonium species Limonium myrianthum, Limonium leptophyllum, and Limonium gmelinii afforded a new compound (2R,3S)-2,3,4-trihydroxy-2-methylbutyl gallate (1) and twenty known compounds (2–21). Each species displayed different profiles in their phytochemical constituents. The isolated compounds (1–21) were evaluated for antifungal, antimalarial, and antitrypanosomal activities. Compound 1 showed good activity against chloroquine-resistant and chloroquine-sensitive strains of malaria, while compound 5 displayed moderate antimalarial activity. Compound 14 showed a significant activity against Trypanosoma brucei.

Development of a compound-specific carbon isotope analysis method for 2-methyltetrols, biomarkers for secondary organic aerosols from atmospheric isoprene

The stable carbon isotope compositions of 2-methyltetrols, biomarker compounds for secondary organic aerosols formed from isoprene in the atmosphere, have been determined by gas chromatography/combustion/isotope ratio mass spectrometry (GC/C/IRMS). In this work, isoprene with various δ13C values was used to produce 2-methyltetrols via an oxidation reaction with hydrogen peroxide in sulfuric acid under direct sunlight. The target compounds with different stable carbon isotope compositions were then derivatized by methylboronic acid with a known δ13C value and measured by GC/C/IRMS. With δ13C values of 2-methyltetrols and methylboronic acid predetermined, isotopic fractionation is evaluated for the derivatization process. Through reduplicate δ13C measurements, the carbon isotope analysis achieved excellent reproducibility and high accuracy with an average error of 13C values range from -0.10 to 0.29%, indicating that the derivatization process does not introduce isotopic fractionation. The δ13C values of 2-methyltetrols could be calculated on the basis of the stoichiometric mass balance equation among 2-methyltetrols, methylboronic acid, and methylboronate derivatives. Preliminary tests of 2-methyltetrols in PM2.5 aerosols at two forested sites were conducted and revealed significant differences in their isotope compositions, implying possible application of the method in helping us understand the primary emission, photochemical reaction, or removal processes of isoprene in the atmosphere.

Biosynthesis of 2-C-methyl-D-erythritol in plants by rearrangement of the terpenoid precursor, 1-deoxy-D-xylulose 5-phosphate

Leaves of Liriodendron tulipifera convert 1-deoxy-D-xylulose to 2-C- methyI-D-erythritol via: a skeletal-rearrangement reminiscent of the formation of terpene precursors from 1-deoxy-D-xylulose. The data suggest that 2-C-methyl-D-erythritol 4-phosphate is either an intermediate or a side product of the deoxyxylulose 4-phosphate pathway of terpenoid biosynthesis.

Synthesis of 2-C-methylerythritols and 2-C-methylthreitols via enantiodivergent Sharpless dihydroxylation of trisubstituted olefins

The mevalonate-independent pathway (MIP) is an interesting avenue for antimicrobial lead discovery. Here, we present a unified enantioselective synthesis of all four stereoisomers of 2-C-methyltetrol. These are useful building blocks of many bioactive natural products, including 2-C-methylerythritol phosphate (MEP) of the MIP biosynthetic pathway.

Dihydroxylation of 4-substituted 1,2-dioxines: A concise route to branched erythro sugars

(Chemical Equation Presented) The synthesis of 2-C-branched erythritol derivatives, including the plant sugar (±)-2-C-methylerythritol 2, was achieved through a dihydroxylation/reduction sequence on a series of 4-substituted 1,2-dioxines 3. The asymmetric dihydroxylation of 1,2-dioxines was examined, providing access to optically enriched dihydroxy 1,2-dioxanes 4. The synthesized 1,2-dioxanes were converted to other erythro sugar analogues and tetrahydrofurans through controlled cleavage of the endoperoxide linkage.

Chemo-enzymatic synthesis of all isomers of 2-methylbutane-1,2,3,4-tetraol - Important contributors to atmospheric aerosols

By a combination of stereospecific osmium catalyzed oxidation of dimethyl citraconate and lipase catalysed enantioselective resolution of the formed dimethyl (2R*,3S*)-2,3-dihydroxy-2-methylbutanedioate, followed by reduction, (2R,3S)- and (2S,3R)-2-methylbutane-1,2,3,4-tetraol were isolated. Similar reactions starting with dimethyl mesaconate gave the isomers, (2R,3R)- and (2S,3S)-2-methylbutane-1,2,3,4-tetraol. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

The dioxanone approach to (2S,3R)-2-C-methylerythritol 4-phosphate and 2,4-cyclodiphosphate, and various MEP analogues

(Chemical Equation Presented) Efficient syntheses of the non-mevalonate pathway intermediates 2-C-methylerythritol 4-phosphate (MEP) and 2-C-methylerythritol 2,4-cyclodiphosphate (ME-2,4-cycloPP), as well as the parent tetrol 2-C-methylerythritol, in enantiopure form from (2S,4R)-cis-2-phenyl-4-tert-butyldimethylsilyloxy-1,3-dioxan-5-one are reported. The 2S configuration of the C-methyl group was installed by highly axial-face selective addition of CH3MgBr (20:1) to the chiral dioxanone carbonyl group. Primary selective monophosphorylation and 2,4-bis-phosphorylation, followed by desilation and hydrogenolysis to the free mono-and diphosphates, and, in the latter case, cyclization to form the eight-membered phosphoryl anhydride, afforded MEP and ME-2,4-cycloPP in good yields. The C2 epimeric analogues, 2-C-methylthreitol and its 4-phosphate, were accessed by LiAlH 4 reduction of the cis,cis epoxide of (2S,4R)-4-tert- butyldimethylsilyloxymethyl-5-methylene-2-phenyl-1,3-dioxane, primary-selective phosphorylation, and cleavage of the silyl, benzylidene, and benzyl protecting groups. Regioselective cleavage of the acetal ring of 1,3-benzylidene 2-C-methylerythritol silyl ether by ozonolysis afforded a 1,2,3-triol 3-monobenzoate intermediate that was converted to the novel amino sugar, 1-amino-1-deoxy-2-C-methylerythritol.

Asymmetric synthesis of (S,S)- and (R,R)-2-methylthreitol

The asymmetric synthesis of (S,S)- and (R,R)-2-methylthreitol was carried out, starting from the SAMP or RAMP hydrazone of 2,2-dimethyl-1,3-dioxan-5-one. The protocol involves an enantioselective α-alkylation as a key step. The second stereogenic center was installed by either nucleophilic 1,2-addition or diastereoselective epoxidation with bis(acetylacetonato)oxovanadium(IV) [VO(acac)2] as catalyst. The title compounds were obtained in excellent diastereo- and enantiomeric excesses (≥98% de, 98% ee) and in good overall yields (40-61%). Georg Thieme Verlag Stuttgart.