7564-64-9

Usage

Uses

Used in Pharmaceutical Industry:
3-METHYLPENTANE-1,3,5-TRIOL is used as an intermediate in the synthesis of Mevalonolactone (M339040) for its potential therapeutic applications. Mevalonolactone is a key compound in the mevalonate pathway, which plays a crucial role in the biosynthesis of cholesterol, dolichols, ubiquinones, and isoprenoid compounds. Its potential use in the development of drugs targeting this pathway makes 3-METHYLPENTANE-1,3,5-TRIOL an important precursor in the pharmaceutical industry.
Used in Vitamin and Isoprenoid Synthesis:
3-METHYLPENTANE-1,3,5-TRIOL is used as a starting material in the synthesis of vitamins and isoprenoids, such as steroids. Isoprenoids are a large and diverse class of natural organic compounds derived from isoprene units, and they play essential roles in various biological processes, including cell signaling, membrane integrity, and energy production. Vitamins, on the other hand, are essential nutrients required for various metabolic processes in the body. The ability of 3-METHYLPENTANE-1,3,5-TRIOL to be converted into these vital compounds highlights its importance in the chemical and pharmaceutical industries.

InChI:InChI=1/C6H14O3/c1-6(9,2-4-7)3-5-8/h7-9H,2-5H2,1H3

Synthetic route

3-Methyl-1,5-bis-(tetrahydro-pyran-2-yloxy)-pentan-3-ol → 3-methyl-1,3,5-pentanetriol (7564-64-9)

Conditions	Yield
With toluene-4-sulfonic acid In methanol for 4h; Heating;	90%

dimethyl 3-hydroxy-3-methylglutarate (56652-39-2) → 3-methyl-1,3,5-pentanetriol (7564-64-9)

Conditions	Yield
With boron trifluoride-tetrahydrofuran complex for 18h; Heating;	88%

meglutol (503-49-1) → 3-methyl-1,3,5-pentanetriol (7564-64-9)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 16h;	45%
Multi-step reaction with 2 steps 1: 91 percent / SOCl2 / 0 °C 2: 88 percent / BF3*THF / 18 h / Heating View Scheme

mevalonolactone (674-26-0) → 3-methyl-1,3,5-pentanetriol (7564-64-9)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran
With lithium aluminium tetrahydride In tetrahydrofuran for 18h; Reflux;	2.1 g

1,1-diallylethanol (25201-40-5) → 3-methyl-1,3,5-pentanetriol (7564-64-9)

Conditions	Yield
(i) O3, CH2Cl2, (ii) LiAlH4, THF; Multistep reaction;
With ozone 1.) -50 deg C, 20-30 min; Yield given. Multistep reaction;

1,1-diallylethanol (25201-40-5) → (R/S)-3-methyl-5-hexene-1,3-diol (114580-75-5) + 3-methyl-1,3,5-pentanetriol (7564-64-9)

Conditions	Yield
With lithium aluminium tetrahydride; ozone Product distribution; 1.) CH2Cl2, -78 deg C, 7 min; 2.) THF, RT, 12 h; different ozonolysis temperature;
With lithium aluminium tetrahydride; ozone 1.) CH2Cl2, -78 deg C, 7 min; 2.) THF, RT, 12 h; Yield given. Multistep reaction. Yields of byproduct given;

4-(β-hydroxyethyl)-4-methyl-1,3-dioxane (2018-45-3) → 3-methyl-1,3,5-pentanetriol (7564-64-9)

Conditions	Yield
With oxalic acid at 150℃; under 4484 Torr; for 2.5h;

[1,3]oxathiolane-2,2-diyl-bis-acetic acid diethyl ester (86447-05-4) → 3-methyl-1,3,5-pentanetriol (7564-64-9)

Conditions	Yield
Multi-step reaction with 5 steps 1: 90 percent / LiAlH4 / tetrahydrofuran / 1 h / Heating 2: 100 percent / p-toluenesulphonic acid / CH2Cl2 / 4 h / 0 °C 3: 96 percent / CaCO3, HgCl2 / acetonitrile; H2O / 1 h / Ambient temperature 4: 1) Mg / 1) ether, 2) 0 deg C, 15 min 5: 90 percent / p-toluenesulphonic acid / methanol / 4 h / Heating View Scheme

2,2'-(1,3-oxathiolane-2,2-diyl)bisethanol (86447-06-5) → 3-methyl-1,3,5-pentanetriol (7564-64-9)

Conditions	Yield
Multi-step reaction with 4 steps 1: 100 percent / p-toluenesulphonic acid / CH2Cl2 / 4 h / 0 °C 2: 96 percent / CaCO3, HgCl2 / acetonitrile; H2O / 1 h / Ambient temperature 3: 1) Mg / 1) ether, 2) 0 deg C, 15 min 4: 90 percent / p-toluenesulphonic acid / methanol / 4 h / Heating View Scheme

2,2-bis[2-(tetrahydropyran-2-yloxy)ethyl]-1,3-oxathiolane (86447-07-6) → 3-methyl-1,3,5-pentanetriol (7564-64-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 96 percent / CaCO3, HgCl2 / acetonitrile; H2O / 1 h / Ambient temperature 2: 1) Mg / 1) ether, 2) 0 deg C, 15 min 3: 90 percent / p-toluenesulphonic acid / methanol / 4 h / Heating View Scheme

1,5-bis(tetrahydropyran-2-yloxy)pentan-3-one (86447-08-7) → 3-methyl-1,3,5-pentanetriol (7564-64-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1) Mg / 1) ether, 2) 0 deg C, 15 min 2: 90 percent / p-toluenesulphonic acid / methanol / 4 h / Heating View Scheme

diethyl 1,3-acetonedicarboxylate (105-50-0) → 3-methyl-1,3,5-pentanetriol (7564-64-9)

Conditions

Yield

Multi-step reaction with 6 steps 1: 92 percent / BF3*Et2O / CH2Cl2 / 6 h / Ambient temperature 2: 90 percent / LiAlH4 / tetrahydrofuran / 1 h / Heating 3: 100 percent / p-toluenesulphonic acid / CH2Cl2 / 4 h / 0 °C 4: 96 percent / CaCO3, HgCl2 / acetonitrile; H2O / 1 h / Ambient temperature 5: 1) Mg / 1) ether, 2) 0 deg C, 15 min 6: 90 percent / p-toluenesulphonic acid / methanol / 4 h / Heating View Scheme

(R)-mevalonolactone (19115-49-2) → 3-methyl-1,3,5-pentanetriol (7564-64-9)

Conditions	Yield
In tetrahydrofuran

3-methyl-1,3,5-pentanetriol (7564-64-9) + benzaldehyde (100-52-7) → 1,3-O,O-benzylidene-3-methylpentane-1,3,5-triol (877308-88-8)

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 60℃; for 18h;	100%
With toluene-4-sulfonic acid In toluene at 60℃; for 24h;	63%

3-methyl-1,3,5-pentanetriol (7564-64-9) → mevalonolactone (674-26-0)

Conditions	Yield
With pyridinium chlorochromate In dichloromethane for 4h; Ambient temperature;	92%
With aluminum oxide; sodium bromite In dichloromethane for 1.5h; Ambient temperature;	85%
With peracetic acid; sodium bromide In ethyl acetate at 39.9℃; for 2h;	83%
With 1-methyl-1H-imidazole; [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate In acetonitrile at 22℃; for 6h;	83%

3-methyl-1,3,5-pentanetriol (7564-64-9) → meglutol (503-49-1)

Conditions	Yield
In acetic acid butyl ester; nitric acid	85%

3-methyl-1,3,5-pentanetriol (7564-64-9) + 4,4'-dimethoxytrityl chloride (40615-36-9) → 1,5-bis-dimethoxytrityloxy-3-methyl-pentan-3-ol (1033113-30-2)

Conditions	Yield
With dmap In pyridine at 0 - 20℃;	78%

3-methyl-1,3,5-pentanetriol (7564-64-9) + p-toluenesulfonyl chloride (98-59-9) → 3-hydroxy-3-methylpentane-1,5-diyl bis(4-methylbenzenesulfonate)

Conditions	Yield
With dmap; triethylamine In acetonitrile at 0 - 20℃; for 5h; Inert atmosphere;	73%

3-methyl-1,3,5-pentanetriol (7564-64-9) + 2,2-dimethoxy-propane (77-76-9) → 1,3-O,O-isopropylidene-3-methylpentane-1,3,5-triol (154066-61-2)

Conditions	Yield
With camphor-10-sulfonic acid In acetone at 20℃; for 24h;	66%
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 80 - 90℃; for 3h;	42.5%

3-methyl-1,3,5-pentanetriol (7564-64-9) + epichlorohydrin (106-89-8) → 3-Methyl-1,5-bis-oxiranylmethoxy-pentan-3-ol

Conditions	Yield
With potassium hydroxide In dimethyl sulfoxide at 40℃; for 6h;	65%

3-methyl-1,3,5-pentanetriol (7564-64-9) + C6H11BO2 + sodium hydride (7646-69-7) → C10H16BO3(1-)*Na(1+)

Conditions	Yield
In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;	63%

3-methyl-1,3,5-pentanetriol (7564-64-9) + tert-butyldimethylsilyl chloride (18162-48-6) → 5-{[tert-butyl(dimethyl)silyl]oxy}-3-methylpentane-1,3-diol (861389-35-7)

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	50%

3-methyl-1,3,5-pentanetriol (7564-64-9) + Trimethylhydroquinone (700-13-0) → 2-(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-benzo[1,2-b]pyran-2-yl)ethanol (79907-48-5)

Conditions	Yield
With hydrogenchloride; zinc(II) chloride In 1,4-dioxane; toluene at 100℃; for 6h;	47%

pyridine (110-86-1) + Mn3O((CH3)3CCO2)6(pyridine)3 + 3-methyl-1,3,5-pentanetriol (7564-64-9) + tetramethyl ammoniumhydroxide (75-59-2) + acetonitrile (75-05-8) → (Me4N)2[MnIII13MnIV2O10(OH)2(3-methyl-1,3,5-pentanetriol(-3H))4(2-hydroxymethyl-3-methylbutane-1,3-diol(-3H))2((CH3)3CCO2)8(py)2]((CH3)3CCO2)2H*2py*2H2O

Conditions	Yield
for 1h;	25%

3-methyl-1,3,5-pentanetriol (7564-64-9) → 3-hydroxy-3-methylcadaverine (133213-14-6)

Conditions	Yield
With hydrogen azide; triphenylphosphine; 2,2'-azobis(isobutyronitrile) In tetrahydrofuran; benzene 1) RT, 1h, 2) 50 deg C, 3h; Yield given;

3-methyl-1,3,5-pentanetriol (7564-64-9) → (S)-mevalonolactone (19022-60-7) + (R)-mevalonolactone (19115-49-2)

Conditions	Yield
In water at 30℃; for 72h; Gluconobacter scleroideus IAM 1842; Yield given. Title compound not separated from byproducts;
In water at 30℃; Product distribution; different Gluconobacters and time of incubation;

3-methyl-1,3,5-pentanetriol (7564-64-9) → 1,3-O,O-isopropylidene-5-O-(t-butyldiphenylsilyl)-3-methylpentane-1,3,5-triol (877308-89-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 66 percent / camphorsulphonic acid / acetone / 24 h / 20 °C 2: 85 percent / triethylamine; DMAP / CH2Cl2 / 12 h / 20 °C View Scheme

3-methyl-1,3,5-pentanetriol (7564-64-9) → 1,3-O,O-benzylidene-5-O-(t-butyldiphenylsilyl)-3-methylpentane-1,3,5-triol (877308-90-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 63 percent / p-toluenesulphonic acid monohydrate / toluene / 24 h / 60 °C 2: 90 percent / triethylamine; DMAP / CH2Cl2 / 12 h / 20 °C View Scheme

3-methyl-1,3,5-pentanetriol (7564-64-9) → 5-(tert-butyl-diphenyl-silanyloxy)-3-methyl-pentane-1,3-diol

Conditions	Yield
Multi-step reaction with 3 steps 1: 63 percent / p-toluenesulphonic acid monohydrate / toluene / 24 h / 60 °C 2: 90 percent / triethylamine; DMAP / CH2Cl2 / 12 h / 20 °C 3: 85 percent / ZnBr2 / CH2Cl2 / 3 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: 66 percent / camphorsulphonic acid / acetone / 24 h / 20 °C 2: 85 percent / triethylamine; DMAP / CH2Cl2 / 12 h / 20 °C 3: 86 percent / ZnBr2 / CH2Cl2 / 1 h / 20 °C View Scheme

3-methyl-1,3,5-pentanetriol (7564-64-9) → 5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-3-methyl-pentanal

Conditions	Yield
Multi-step reaction with 2 steps 1: 50 percent / triethylamine / CH2Cl2 / 20 °C 2: oxalyl chloride; dimethyl sulfoxide; triethylamine / CH2Cl2 / -78 - 20 °C View Scheme

3-methyl-1,3,5-pentanetriol (7564-64-9) → ethyl (2E)-7-bromo-5-(methoxymethoxy)-5-methylhept-2-enoate

Conditions

Yield

Multi-step reaction with 6 steps 1: 50 percent / triethylamine / CH2Cl2 / 20 °C 2: oxalyl chloride; dimethyl sulfoxide; triethylamine / CH2Cl2 / -78 - 20 °C 3: 60 percent / CH2Cl2 / -78 - 20 °C 4: 79 percent / diisopropylethylamine / CH2Cl2 / 0 - 20 °C 5: 81 percent / hydrogen fluoride; pyridine / tetrahydrofuran / 0 - 20 °C 6: 45 percent / carbon tetrabromide; triphenylphosphine / CH2Cl2 / 0 - 20 °C View Scheme

3-methyl-1,3,5-pentanetriol (7564-64-9) → ethyl (2E)-7-hydroxy-5-(methoxymethoxy)-5-methylhept-2-enoate (861389-37-9)

Conditions	Yield
Multi-step reaction with 5 steps 1: 50 percent / triethylamine / CH2Cl2 / 20 °C 2: oxalyl chloride; dimethyl sulfoxide; triethylamine / CH2Cl2 / -78 - 20 °C 3: 60 percent / CH2Cl2 / -78 - 20 °C 4: 79 percent / diisopropylethylamine / CH2Cl2 / 0 - 20 °C 5: 81 percent / hydrogen fluoride; pyridine / tetrahydrofuran / 0 - 20 °C View Scheme

Upstream product

• 674-26-0 mevalonolactone 
• 25201-40-5 1,1-diallylethanol 
• 56652-39-2 dimethyl 3-hydroxy-3-methylglutarate 
• 2018-45-3 4-(β-hydroxyethyl)-4-methyl-1,3-dioxane 
• 86447-05-4 [1,3]oxathiolane-2,2-diyl-bis-acetic acid diethyl ester 
• 86447-06-5 2,2'-(1,3-oxathiolane-2,2-diyl)bisethanol 
• 86447-07-6 2,2-bis[2-(tetrahydropyran-2-yloxy)ethyl]-1,3-oxathiolane 
• 86447-08-7 1,5-bis(tetrahydropyran-2-yloxy)pentan-3-one 
• 105-50-0 diethyl 1,3-acetonedicarboxylate 
• 503-49-1 meglutol 
• 19115-49-2 (R)-mevalonolactone 

Downstream Products

• 674-26-0 mevalonolactone 
• 877308-88-8 1,3-O,O-benzylidene-3-methylpentane-1,3,5-triol 
• 877308-89-9 1,3-O,O-isopropylidene-5-O-(t-butyldiphenylsilyl)-3-methylpentane-1,3,5-triol 
• 877308-90-2 1,3-O,O-benzylidene-5-O-(t-butyldiphenylsilyl)-3-methylpentane-1,3,5-triol 
• 60018-14-6 (S)-(-)-2-[6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl]ethanol 
• 101268-70-6 (RS)-5-benzyloxy-3-hydroxy-3-methylpentanoic acid 
• 87137-49-3 methyl (RS)-5-benzyloxy-3-hydroxy-3-methylpentanoate 
• 154066-62-3 4-(2-Benzyloxy-ethyl)-2,2,4-trimethyl-[1,3]dioxane 
• 154170-47-5 5-benzyloxy-3-methylpentane-1,3-diol 
• 503-49-1 meglutol 
• 871026-48-1 3,5-dihydroxy-3-methylpentyl benzoate 
• 19125-34-9 1-phenylpiperidin-4-one 
• 117896-69-2 1-phenyl-4-hydroxypiperidine 

Relevant academic research and scientific papers

POLYMERS PREPARED FROM MEVALONOLACTONE AND DERIVATIVES

Described herein polymer precursor compounds (aka polymer building blocks) of derived from biobased compounds, and specifically biobased mevalonolactone and its related derivatives. Through oxidation these biobased precursors can be reacted to yield building blocks for (unsaturated-) polyesters, polyester polyols and polyamides, as well as precursors for glycidyl esters and omega-alkenyl esters. Through reduction, these biobased precursors can be reacted to yield building blocks for (unsaturated-) polyesters, polyester polyols, polycarbonates, as well as precursors for glycidyl ethers and omega-alkenyl ethers. Through nucleophilic ring opening and/or amidation, these biobased precursors can be reacted to yield building blocks for polyester polyols, chain-extender for polyurethanes, or polyester-amides.

POLYMERS PREPARED FROM MEVALONOLACTONE AND DERIVATIVES

Described herein polymer precursor compounds (aka polymer building blocks) of derived from biobased compounds, and specifically biobased mevalonolactone and its related derivatives. Through oxidation these biobased precursors can be reacted to yield building blocks for (unsaturated-) polyesters, polyester polyols and polyamides, as well as precursors for glycidyl esters and omega-alkenyl esters. Through reduction, these biobased precursors can be reacted to yield building blocks for (unsaturated-) polyesters, polyester polyols, polycarbonates, as well as precursors for glycidyl ethers and omega-alkenyl ethers. Through nucleophilic ring opening and/or amidation, these biobased precursors can be reacted to yield building blocks for polyester polyols, chain-extender for polyurethanes, or polyester-amides.

Efficient and Selective Cu/Nitroxyl-Catalyzed Methods for Aerobic Oxidative Lactonization of Diols

Cu/nitroxyl catalysts have been identified that promote highly efficient and selective aerobic oxidative lactonization of diols under mild reaction conditions using ambient air as the oxidant. The chemo- and regioselectivity of the reaction may be tuned by changing the identity of the nitroxyl cocatalyst. A Cu/ABNO catalyst system (ABNO = 9-azabicyclo[3.3.1]nonan-N-oxyl) shows excellent reactivity with symmetrical diols and hindered unsymmetrical diols, whereas a Cu/TEMPO catalyst system (TEMPO = 2,2,6,6-tetramethyl-1-piperidinyl-N-oxyl) displays excellent chemo- and regioselectivity for the oxidation of less hindered unsymmetrical diols. These catalyst systems are compatible with all classes of alcohols (benzylic, allylic, aliphatic), mediate efficient lactonization of 1,4-, 1,5-, and some 1,6-diols, and tolerate diverse functional groups, including alkenes, heterocycles, and other heteroatom-containing groups.

REACTION OF BORIC ACID WITH 3-METHYLPENTANE-1,3,5-TRIOL

Cyclic esters of boric acid and 3-methyl-1,3,5-pentanetriol showing efficient fungicidal activity were prepared.

Oxidation of putrescine and cadaverine derivatives by diamine oxidases

A range of putrescine and cadaverine derivatives has been synthesized and assayed as substrates for the diamine oxidases from pea seedlings and pig kidney. KM and Vmax data are reported, mainly for the pea enzyme. N-Alkylputrescines and C-alkylcadaverines are generally poorer substrates than the parent compounds with up to 4500-fold reduction in Vmax. There is significantly less variation in KM values, indicating that the binding site of the pea enzyme is relatively non-specific and that enzymic specificity lies at the catalytic stage. This suggests that poor substrates might act as convenient, short-lived inhibitors of diamine oxidases.

A New Flexible Synthesis of (R,S)-Mevalonolactone

By selective ozonolysis of the diene (5), a new synthesis of (R,S)-mevalonolactone (1a) has been developed, which can be adapted to other compounds related to (1a).This has been exemplified by the synthesis of the monodeuteriated triol (4d) and dideuteriated mevalonolactone (1d).

Oxidation of Diols to Lactones: A Simple Synthesis of (+/-)-Mevalonolactone

Oxidation of 1,4-diol and 1,5-diol with pyridinium chlorochromate or chromium(V) reagent yields γ- and δ-lactones respectively in good yields.The mildness of this method has been tested succesfully in a simple synthesis of (+/-)-mevalonolactone (7).