CAS No.55682-83-2,METHYL 3-HYDROXYTETRADECANOATE Suppliers

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Tetradecanoic acid,3-hydroxy-, methyl ester

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METHYL 3-HYDROXYTETRADECANOATE

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Shandong Mopai Biotechnology Co., LTD

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Tetradecanoic acid,3-hydroxy-, methyl ester

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Henan Tianfu Chemical Co., Ltd.

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Tetradecanoic acid,3-hydroxy-, methyl ester

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Antimex Chemical Limied

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[1,1'-Biphenyl]-3-sulfonicacid,4-[2-[4,5-dihydro-3-methyl-5-oxo-1-(4-sulfophenyl)-1H-pyrazol-4-yl]diazenyl]-3',5-dimethyl-4'-[2-[4-[[(4-methylphenyl)sulfonyl]oxy]phenyl]diazenyl]-,sodium salt (1:2)

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ZHEJIANG JIUZHOU CHEM CO.,LTD

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METHYL 3-HYDROXYTETRADECANOATE

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Finetech Industry Limited

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Debye Scientific

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Methyl 3-hydroxytetradecanoate

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CHEMOS GmbH

Tetradecanoic acid,3-hydroxy-, methyl ester

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Synthetic route

: 22348-97-6
methyl 3-oxotetradecanoate

: 55682-83-2
(+/-)-3-hydroxytetradecanoic acid methyl ester

Conditions

Conditions	Yield
With sodium tetrahydroborate In methanol at 0℃;	86%
With sodium tetrahydroborate In methanol at 5 - 10℃; for 2h;
With sodium tetrahydroborate In tetrahydrofuran; methanol

: 112-54-9
Dodecanal

: 96-32-2
bromoacetic acid methyl ester

: 55682-83-2
(+/-)-3-hydroxytetradecanoic acid methyl ester

Conditions

Conditions	Yield
With zinc In benzene for 2h; Heating;	82%

: 143-07-7
lauric acid

monomethoxy poly(ethylene glycol): monomethoxy poly(ethylene glycol)

: 55682-83-2
(+/-)-3-hydroxytetradecanoic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrahydrofuran / 0 - 20 °C 2: 14.72 g / 72 h / 20 °C 3: 86 percent / sodium borohydride / methanol / 0 °C View Scheme

: 3867-67-2
N-laurylimidazole

: 55682-83-2
(+/-)-3-hydroxytetradecanoic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 14.72 g / 72 h / 20 °C 2: 86 percent / sodium borohydride / methanol / 0 °C View Scheme

: 112-16-3
n-dodecanoyl chloride

glycerol-1-caprinate-3-stearate: glycerol-1-caprinate-3-stearate

: 55682-83-2
(+/-)-3-hydroxytetradecanoic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine / CH2Cl2 / 0 deg C, 1 h then r.t., 4 h 2: 3 h / Heating 3: NaBH4 / methanol / 2 h / 5 - 10 °C View Scheme

: 88222-72-4
3-oxomyristic acid

: 55682-83-2
(+/-)-3-hydroxytetradecanoic acid methyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 3 h / Heating 2: NaBH4 / methanol / 2 h / 5 - 10 °C View Scheme

polyhydroxyalkanoate: polyhydroxyalkanoate

A: C14H20O4

B: 1487-49-6
3-hydroxybutyric acid methyl ester

C: 7367-87-5
3-hydroxyoctanoic acid methyl ester

D: 62675-82-5
methyl 3-hydroxydecanoate

E: 72864-23-4
β-hydroxydodecanoic acid methyl ester

F: 55682-83-2
(+/-)-3-hydroxytetradecanoic acid methyl ester

G: 129880-16-6
3-hydroxy-5-phenyl-pentanoic acid methyl ester

Conditions

Conditions	Yield
Product distribution / selectivity;

...Expand

polyhydroxyalkanoate: polyhydroxyalkanoate

A: C13H15FO4

B: 1487-49-6
3-hydroxybutyric acid methyl ester

C: 7367-87-5
3-hydroxyoctanoic acid methyl ester

D: 21188-58-9
methyl 3-hydroxyhexanoate

E: 62675-82-5
methyl 3-hydroxydecanoate

F: 56009-31-5
3-hydroxy valeric acid methyl ester

G: 15889-95-9
methyl 3-hydroxyheptanoate

H: 83968-06-3
methyl 3-hydroxy-nonanoate

I: 72864-23-4
β-hydroxydodecanoic acid methyl ester

J: 55682-83-2
(+/-)-3-hydroxytetradecanoic acid methyl ester

Conditions

Conditions	Yield
Product distribution / selectivity;

...Expand

polyhydroxyalkanoate: polyhydroxyalkanoate

A: C13H15FO4

B: 1487-49-6
3-hydroxybutyric acid methyl ester

C: 7367-87-5
3-hydroxyoctanoic acid methyl ester

D: 21188-58-9
methyl 3-hydroxyhexanoate

E: 62675-82-5
methyl 3-hydroxydecanoate

F: 72864-23-4
β-hydroxydodecanoic acid methyl ester

G: 55682-83-2
(+/-)-3-hydroxytetradecanoic acid methyl ester

Conditions

Conditions	Yield
Product distribution / selectivity;

...Expand

polyhydroxyalkanoate: polyhydroxyalkanoate

A: C13H15FO4

B: 1487-49-6
3-hydroxybutyric acid methyl ester

C: 7367-87-5
3-hydroxyoctanoic acid methyl ester

D: 21188-58-9
methyl 3-hydroxyhexanoate

E: 62675-82-5
methyl 3-hydroxydecanoate

F: 15889-95-9
methyl 3-hydroxyheptanoate

G: 83968-06-3
methyl 3-hydroxy-nonanoate

H: 72864-23-4
β-hydroxydodecanoic acid methyl ester

I: 55682-83-2
(+/-)-3-hydroxytetradecanoic acid methyl ester

Conditions

Conditions	Yield
Product distribution / selectivity;

...Expand

: 62673-11-4
methyl 3-methoxytetradecanoate

: 55682-83-2
(+/-)-3-hydroxytetradecanoic acid methyl ester

Conditions

Conditions	Yield
With methanol; boron trifluoride at 80℃; for 0.0833333h;

: 67-56-1
methanol

: 1961-72-4
3-hydroxytetradecanoic acid

: 55682-83-2
(+/-)-3-hydroxytetradecanoic acid methyl ester

Conditions

Conditions	Yield
With boron trifluoride at 105℃; for 0.75h;

: 67-56-1
methanol

lipopolysaccharide from Sinorhizobium fredii HH103, rkpA: lipopolysaccharide from Sinorhizobium fredii HH103, rkpA

A: 775341-88-3
27-hydroxy-octacosanoic acid methyl ester

B: 2420-36-2
3-hydroxy-octadecanoic acid methyl ester

C: 51883-36-4
β-hydroxyhexadecanoic acid methyl ester

D: 150024-70-7
methyl 3-hydroxytridecanoate

E: 112538-88-2
Methyl-3-hydroxypentadecanoat

F: 72864-23-4
β-hydroxydodecanoic acid methyl ester

G: 55682-83-2
(+/-)-3-hydroxytetradecanoic acid methyl ester

H: Methyl 29-hydroxytriacontanoate

I: C18H36O3

J: C20H40O3

Conditions

Conditions	Yield
With hydrogenchloride In water at 80℃; for 16h;

...Expand

: 67-56-1
methanol

lipopolysaccharide from Sinorhizobium fredii HH103, rkpM: lipopolysaccharide from Sinorhizobium fredii HH103, rkpM

A: 775341-88-3
27-hydroxy-octacosanoic acid methyl ester

B: 2420-36-2
3-hydroxy-octadecanoic acid methyl ester

C: 51883-36-4
β-hydroxyhexadecanoic acid methyl ester

D: 150024-70-7
methyl 3-hydroxytridecanoate

E: 112538-88-2
Methyl-3-hydroxypentadecanoat

F: 72864-23-4
β-hydroxydodecanoic acid methyl ester

G: 55682-83-2
(+/-)-3-hydroxytetradecanoic acid methyl ester

H: Methyl 29-hydroxytriacontanoate

I: C18H36O3

J: C20H40O3

Conditions

Conditions	Yield
With hydrogenchloride In water at 80℃; for 16h;

...Expand

: 55682-83-2
(+/-)-3-hydroxytetradecanoic acid methyl ester

: 2687-43-6
O-benzylhydoxylamine hydrochloride

: 444023-10-3
3-hydroxy-tetradecanoic acid benzyloxy-amide

Conditions

Conditions	Yield
With trimethylaluminum In n-heptane; dichloromethane at 0 - 20℃;	85%

: 55682-83-2
(+/-)-3-hydroxytetradecanoic acid methyl ester

: 106-95-6
allyl bromide

: (2RS,3SR)-2-allyl-3-hydroxytetradecanoic acid methyl ester

Conditions

Conditions	Yield
Stage #1: (+/-)-3-hydroxytetradecanoic acid methyl ester With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: allyl bromide With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran; hexane at -78℃; for 1h; Further stages.;	62%

: 55682-83-2
(+/-)-3-hydroxytetradecanoic acid methyl ester

: 1961-72-4
3-hydroxytetradecanoic acid

Conditions

Conditions	Yield
With sodium hydroxide In methanol Ambient temperature; Yield given;

: 64312-89-6
Mosher's acid chloride

: 55682-83-2
(+/-)-3-hydroxytetradecanoic acid methyl ester

: 3-(3,3,3-Trifluoro-2-methoxy-2-phenyl-propionyloxy)-tetradecanoic acid methyl ester

Conditions

Conditions	Yield
With pyridine

: 55682-83-2
(+/-)-3-hydroxytetradecanoic acid methyl ester

: (SR)-1-[(RS)-4-methylene-5-oxotetrahydrofuran-3-yl]dodecyl acetate

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 62 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 1 h / -78 °C 2.1: 68 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 2 h / 0 - 20 °C 3.1: 76 percent / 4-(dimethylamino)pyridine; imidazole / CH2Cl2 / 3 h / 20 °C 4.1: 91 percent / 4-(dimethylamino)pyridine; triethylamine / CH2Cl2 / 2 h / 20 °C 5.1: ozone / CH2Cl2 / -78 °C 5.2: 78 percent / Et2NH / CH2Cl2 / 1.5 h / -78 - 20 °C 6.1: 72 percent / sodium chlorite; sodium dihydrogen phosphate dihydrate; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 2.5 h / 20 °C 7.1: 40 percent / trifluoroacetic acid / methanol / 0.5 h / 20 °C View Scheme

Yield

Multi-step reaction with 7 steps
1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C
1.2: 62 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 1 h / -78 °C
2.1: 68 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 2 h / 0 - 20 °C
3.1: 76 percent / 4-(dimethylamino)pyridine; imidazole / CH2Cl2 / 3 h / 20 °C
4.1: 91 percent / 4-(dimethylamino)pyridine; triethylamine / CH2Cl2 / 2 h / 20 °C
5.1: ozone / CH2Cl2 / -78 °C
5.2: 78 percent / Et2NH / CH2Cl2 / 1.5 h / -78 - 20 °C
6.1: 72 percent / sodium chlorite; sodium dihydrogen phosphate dihydrate; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 2.5 h / 20 °C
7.1: 40 percent / trifluoroacetic acid / methanol / 0.5 h / 20 °C
View Scheme

: 55682-83-2
(+/-)-3-hydroxytetradecanoic acid methyl ester

: [(2SR,3RS)-4-methylene-5-oxo-2-undecyltetrahydrofuran-3-yl]methyl acetate

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 62 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 1 h / -78 °C 2.1: 68 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 2 h / 0 - 20 °C 3.1: 76 percent / 4-(dimethylamino)pyridine; imidazole / CH2Cl2 / 3 h / 20 °C 4.1: 91 percent / 4-(dimethylamino)pyridine; triethylamine / CH2Cl2 / 2 h / 20 °C 5.1: ozone / CH2Cl2 / -78 °C 5.2: 78 percent / Et2NH / CH2Cl2 / 1.5 h / -78 - 20 °C 6.1: 72 percent / sodium chlorite; sodium dihydrogen phosphate dihydrate; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 2.5 h / 20 °C 7.1: 40 percent / trifluoroacetic acid / methanol / 0.5 h / 20 °C View Scheme

Yield

: 55682-83-2
(+/-)-3-hydroxytetradecanoic acid methyl ester

: (SR)-4-[(RS)-1-hydroxydodecyl]-3-methylenedihydrofuran-2(3H)-one

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 62 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 1 h / -78 °C 2.1: 68 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 2 h / 0 - 20 °C 3.1: 76 percent / 4-(dimethylamino)pyridine; imidazole / CH2Cl2 / 3 h / 20 °C 4.1: 91 percent / 4-(dimethylamino)pyridine; triethylamine / CH2Cl2 / 2 h / 20 °C 5.1: ozone / CH2Cl2 / -78 °C 5.2: 78 percent / Et2NH / CH2Cl2 / 1.5 h / -78 - 20 °C 6.1: 72 percent / sodium chlorite; sodium dihydrogen phosphate dihydrate; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 2.5 h / 20 °C 7.1: 42 percent / acetyl chloride / methanol / 0.5 h / 20 °C View Scheme
Multi-step reaction with 8 steps 1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 62 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 1 h / -78 °C 2.1: 68 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 2 h / 0 - 20 °C 3.1: 76 percent / 4-(dimethylamino)pyridine; imidazole / CH2Cl2 / 3 h / 20 °C 4.1: 91 percent / 4-(dimethylamino)pyridine; triethylamine / CH2Cl2 / 2 h / 20 °C 5.1: ozone / CH2Cl2 / -78 °C 5.2: 78 percent / Et2NH / CH2Cl2 / 1.5 h / -78 - 20 °C 6.1: 72 percent / sodium chlorite; sodium dihydrogen phosphate dihydrate; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 2.5 h / 20 °C 7.1: 94 percent / CH2Cl2; diethyl ether / 0.5 h / 20 °C 8.1: 52 percent / acetyl chloride / methanol / 0.5 h / 20 °C View Scheme

Yield

Multi-step reaction with 7 steps
1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C
1.2: 62 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 1 h / -78 °C
2.1: 68 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 2 h / 0 - 20 °C
3.1: 76 percent / 4-(dimethylamino)pyridine; imidazole / CH2Cl2 / 3 h / 20 °C
4.1: 91 percent / 4-(dimethylamino)pyridine; triethylamine / CH2Cl2 / 2 h / 20 °C
5.1: ozone / CH2Cl2 / -78 °C
5.2: 78 percent / Et2NH / CH2Cl2 / 1.5 h / -78 - 20 °C
6.1: 72 percent / sodium chlorite; sodium dihydrogen phosphate dihydrate; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 2.5 h / 20 °C
7.1: 42 percent / acetyl chloride / methanol / 0.5 h / 20 °C
View Scheme

Multi-step reaction with 8 steps
1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C
1.2: 62 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 1 h / -78 °C
2.1: 68 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 2 h / 0 - 20 °C
3.1: 76 percent / 4-(dimethylamino)pyridine; imidazole / CH2Cl2 / 3 h / 20 °C
4.1: 91 percent / 4-(dimethylamino)pyridine; triethylamine / CH2Cl2 / 2 h / 20 °C
5.1: ozone / CH2Cl2 / -78 °C
5.2: 78 percent / Et2NH / CH2Cl2 / 1.5 h / -78 - 20 °C
6.1: 72 percent / sodium chlorite; sodium dihydrogen phosphate dihydrate; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 2.5 h / 20 °C
7.1: 94 percent / CH2Cl2; diethyl ether / 0.5 h / 20 °C
8.1: 52 percent / acetyl chloride / methanol / 0.5 h / 20 °C
View Scheme

: 55682-83-2
(+/-)-3-hydroxytetradecanoic acid methyl ester

: (4RS,5SR)-4-hydroxymethyl-3-methylene-5-undecyldihydrofuran-2(3H)-one

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 62 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 1 h / -78 °C 2.1: 68 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 2 h / 0 - 20 °C 3.1: 76 percent / 4-(dimethylamino)pyridine; imidazole / CH2Cl2 / 3 h / 20 °C 4.1: 91 percent / 4-(dimethylamino)pyridine; triethylamine / CH2Cl2 / 2 h / 20 °C 5.1: ozone / CH2Cl2 / -78 °C 5.2: 78 percent / Et2NH / CH2Cl2 / 1.5 h / -78 - 20 °C 6.1: 72 percent / sodium chlorite; sodium dihydrogen phosphate dihydrate; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 2.5 h / 20 °C 7.1: 42 percent / acetyl chloride / methanol / 0.5 h / 20 °C View Scheme
Multi-step reaction with 8 steps 1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 62 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 1 h / -78 °C 2.1: 68 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 2 h / 0 - 20 °C 3.1: 76 percent / 4-(dimethylamino)pyridine; imidazole / CH2Cl2 / 3 h / 20 °C 4.1: 91 percent / 4-(dimethylamino)pyridine; triethylamine / CH2Cl2 / 2 h / 20 °C 5.1: ozone / CH2Cl2 / -78 °C 5.2: 78 percent / Et2NH / CH2Cl2 / 1.5 h / -78 - 20 °C 6.1: 72 percent / sodium chlorite; sodium dihydrogen phosphate dihydrate; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 2.5 h / 20 °C 7.1: 94 percent / CH2Cl2; diethyl ether / 0.5 h / 20 °C 8.1: 36 percent / acetyl chloride / methanol / 0.5 h / 20 °C View Scheme

Yield

Multi-step reaction with 7 steps
1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C
1.2: 62 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 1 h / -78 °C
2.1: 68 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 2 h / 0 - 20 °C
3.1: 76 percent / 4-(dimethylamino)pyridine; imidazole / CH2Cl2 / 3 h / 20 °C
4.1: 91 percent / 4-(dimethylamino)pyridine; triethylamine / CH2Cl2 / 2 h / 20 °C
5.1: ozone / CH2Cl2 / -78 °C
5.2: 78 percent / Et2NH / CH2Cl2 / 1.5 h / -78 - 20 °C
6.1: 72 percent / sodium chlorite; sodium dihydrogen phosphate dihydrate; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 2.5 h / 20 °C
7.1: 42 percent / acetyl chloride / methanol / 0.5 h / 20 °C
View Scheme

Multi-step reaction with 8 steps
1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C
1.2: 62 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 1 h / -78 °C
2.1: 68 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 2 h / 0 - 20 °C
3.1: 76 percent / 4-(dimethylamino)pyridine; imidazole / CH2Cl2 / 3 h / 20 °C
4.1: 91 percent / 4-(dimethylamino)pyridine; triethylamine / CH2Cl2 / 2 h / 20 °C
5.1: ozone / CH2Cl2 / -78 °C
5.2: 78 percent / Et2NH / CH2Cl2 / 1.5 h / -78 - 20 °C
6.1: 72 percent / sodium chlorite; sodium dihydrogen phosphate dihydrate; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 2.5 h / 20 °C
7.1: 94 percent / CH2Cl2; diethyl ether / 0.5 h / 20 °C
8.1: 36 percent / acetyl chloride / methanol / 0.5 h / 20 °C
View Scheme

: 55682-83-2
(+/-)-3-hydroxytetradecanoic acid methyl ester

: (2RS,3SR)-2-allyltetradecane-1,3-diol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 62 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 1 h / -78 °C 2.1: 68 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 2 h / 0 - 20 °C View Scheme

: 55682-83-2
(+/-)-3-hydroxytetradecanoic acid methyl ester

: (4RS,5SR)-4-[(tert-butyldimethylsilyloxy)methyl]hexadec-1-en-5-ol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 62 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 1 h / -78 °C 2.1: 68 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 2 h / 0 - 20 °C 3.1: 76 percent / 4-(dimethylamino)pyridine; imidazole / CH2Cl2 / 3 h / 20 °C View Scheme

: 55682-83-2
(+/-)-3-hydroxytetradecanoic acid methyl ester

: (4RS,5SR)-4-[(tert-butyldimethylsilyloxy)methyl]hexadec-1-en-5-yl acetate

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 62 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 1 h / -78 °C 2.1: 68 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 2 h / 0 - 20 °C 3.1: 76 percent / 4-(dimethylamino)pyridine; imidazole / CH2Cl2 / 3 h / 20 °C 4.1: 91 percent / 4-(dimethylamino)pyridine; triethylamine / CH2Cl2 / 2 h / 20 °C View Scheme

Yield

Multi-step reaction with 4 steps
1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C
1.2: 62 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 1 h / -78 °C
2.1: 68 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 2 h / 0 - 20 °C
3.1: 76 percent / 4-(dimethylamino)pyridine; imidazole / CH2Cl2 / 3 h / 20 °C
4.1: 91 percent / 4-(dimethylamino)pyridine; triethylamine / CH2Cl2 / 2 h / 20 °C
View Scheme

: 55682-83-2
(+/-)-3-hydroxytetradecanoic acid methyl ester

: (3RS,4SR)-3-[(tert-butyldimethylsilyloxy)methyl]-2-formylpentadec-1-en-4-yl acetate

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C 1.2: 62 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 1 h / -78 °C 2.1: 68 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 2 h / 0 - 20 °C 3.1: 76 percent / 4-(dimethylamino)pyridine; imidazole / CH2Cl2 / 3 h / 20 °C 4.1: 91 percent / 4-(dimethylamino)pyridine; triethylamine / CH2Cl2 / 2 h / 20 °C 5.1: ozone / CH2Cl2 / -78 °C 5.2: 78 percent / Et2NH / CH2Cl2 / 1.5 h / -78 - 20 °C View Scheme

Yield

Multi-step reaction with 5 steps
1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C
1.2: 62 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 1 h / -78 °C
2.1: 68 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 2 h / 0 - 20 °C
3.1: 76 percent / 4-(dimethylamino)pyridine; imidazole / CH2Cl2 / 3 h / 20 °C
4.1: 91 percent / 4-(dimethylamino)pyridine; triethylamine / CH2Cl2 / 2 h / 20 °C
5.1: ozone / CH2Cl2 / -78 °C
5.2: 78 percent / Et2NH / CH2Cl2 / 1.5 h / -78 - 20 °C
View Scheme

: 55682-83-2
(+/-)-3-hydroxytetradecanoic acid methyl ester

: (+/-)-trans-1-benzyl-3-(N-(1,1-dimethylethyl)amino)-4-undecyl-2-azetidinone

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 85 percent / AlMe3 / CH2Cl2; heptane / 0 - 20 °C 2: 84 percent / triphenylphosphine; carbon tetrachloride; triethylamine / acetonitrile / 0 - 20 °C 3: H2 / Pd/C / methanol 4: 90 percent / diisopropylethylamine / acetonitrile / 0.5 h / 0 °C 5: 60 percent / DBU / acetonitrile / 47.5 h / 20 °C 6: 63 percent / NaH / dimethylformamide; various solvent(s) / 7 h / 0 - 20 °C View Scheme

Yield

Multi-step reaction with 6 steps
1: 85 percent / AlMe3 / CH2Cl2; heptane / 0 - 20 °C
2: 84 percent / triphenylphosphine; carbon tetrachloride; triethylamine / acetonitrile / 0 - 20 °C
3: H2 / Pd/C / methanol
4: 90 percent / diisopropylethylamine / acetonitrile / 0.5 h / 0 °C
5: 60 percent / DBU / acetonitrile / 47.5 h / 20 °C
6: 63 percent / NaH / dimethylformamide; various solvent(s) / 7 h / 0 - 20 °C
View Scheme

: 55682-83-2
(+/-)-3-hydroxytetradecanoic acid methyl ester

: (+/-)-trans-1-(tert-butyldiphenylsilyl)-3-(N-(1,1-dimethylethyl)amino)-4-undecyl-2-azetidinone

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 85 percent / AlMe3 / CH2Cl2; heptane / 0 - 20 °C 2: 84 percent / triphenylphosphine; carbon tetrachloride; triethylamine / acetonitrile / 0 - 20 °C 3: H2 / Pd/C / methanol 4: 90 percent / diisopropylethylamine / acetonitrile / 0.5 h / 0 °C 5: 60 percent / DBU / acetonitrile / 47.5 h / 20 °C 6: 32 percent / n-BuLi / tetrahydrofuran; hexane / 0.75 h / -78 °C View Scheme

Yield

Multi-step reaction with 6 steps
1: 85 percent / AlMe3 / CH2Cl2; heptane / 0 - 20 °C
2: 84 percent / triphenylphosphine; carbon tetrachloride; triethylamine / acetonitrile / 0 - 20 °C
3: H2 / Pd/C / methanol
4: 90 percent / diisopropylethylamine / acetonitrile / 0.5 h / 0 °C
5: 60 percent / DBU / acetonitrile / 47.5 h / 20 °C
6: 32 percent / n-BuLi / tetrahydrofuran; hexane / 0.75 h / -78 °C
View Scheme

: 55682-83-2
(+/-)-3-hydroxytetradecanoic acid methyl ester

: 1-hydroxy-4-undecyl-azetidin-2-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 85 percent / AlMe3 / CH2Cl2; heptane / 0 - 20 °C 2: 84 percent / triphenylphosphine; carbon tetrachloride; triethylamine / acetonitrile / 0 - 20 °C 3: H2 / Pd/C / methanol View Scheme

: 55682-83-2
(+/-)-3-hydroxytetradecanoic acid methyl ester

: acetic acid 2-oxo-4-undecyl-azetidin-3-yl ester

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 85 percent / AlMe3 / CH2Cl2; heptane / 0 - 20 °C 2: 84 percent / triphenylphosphine; carbon tetrachloride; triethylamine / acetonitrile / 0 - 20 °C 3: H2 / Pd/C / methanol 4: 90 percent / diisopropylethylamine / acetonitrile / 0.5 h / 0 °C 5: 28 percent / diisopropylethylamine / acetonitrile View Scheme

: 55682-83-2
(+/-)-3-hydroxytetradecanoic acid methyl ester

: (+/-)-trans-3-azido-4-undecyl-2-azetidinone

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 85 percent / AlMe3 / CH2Cl2; heptane / 0 - 20 °C 2: 84 percent / triphenylphosphine; carbon tetrachloride; triethylamine / acetonitrile / 0 - 20 °C 3: H2 / Pd/C / methanol 4: 90 percent / diisopropylethylamine / acetonitrile / 0.5 h / 0 °C 5: 65 percent / trimethylsilyl azide; diisopropylethylamine / acetonitrile / 20 °C View Scheme

: 55682-83-2
(+/-)-3-hydroxytetradecanoic acid methyl ester

: (+/-)-trans-3-(N-(1,1-dimethylethyl)amino)-4-undecyl-2-azetidinone

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 85 percent / AlMe3 / CH2Cl2; heptane / 0 - 20 °C 2: 84 percent / triphenylphosphine; carbon tetrachloride; triethylamine / acetonitrile / 0 - 20 °C 3: H2 / Pd/C / methanol 4: 90 percent / diisopropylethylamine / acetonitrile / 0.5 h / 0 °C 5: 60 percent / DBU / acetonitrile / 47.5 h / 20 °C View Scheme

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