t-butyl 12-benzyloxy-2-icosanyl-5-(5-spiro-2,2-dimethyl-1,3-dioxacyclopentyl)-2-dodecenoate

Base Information

Chemical Name:t-butyl 12-benzyloxy-2-icosanyl-5-(5-spiro-2,2-dimethyl-1,3-dioxacyclopentyl)-2-dodecenoate
CAS No.:201547-38-8
Molecular Formula:C₄₇H₈₂O₅
Molecular Weight:727.165
Hs Code.:

Synonyms:

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Chemical Property of t-butyl 12-benzyloxy-2-icosanyl-5-(5-spiro-2,2-dimethyl-1,3-dioxacyclopentyl)-2-dodecenoate

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Technology Process of t-butyl 12-benzyloxy-2-icosanyl-5-(5-spiro-2,2-dimethyl-1,3-dioxacyclopentyl)-2-dodecenoate

There total 15 articles about t-butyl 12-benzyloxy-2-icosanyl-5-(5-spiro-2,2-dimethyl-1,3-dioxacyclopentyl)-2-dodecenoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 13224-84-5
5-trimethylsilanyl-pent-4-yn-1-ol

: 201547-38-8
t-butyl 12-benzyloxy-2-icosanyl-5-(5-spiro-2,2-dimethyl-1,3-dioxacyclopentyl)-2-dodecenoate

Guidance literature:: Multi-step reaction with 13 steps

1.1: 50 g / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.5 h / -78 - 20 °C

2.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 61.6 g / tetrahydrofuran; hexane / 0.5 h / -78 °C

3.1: 93 percent / LiAlH₄ / diethyl ether / 0 - 20 °C

4.1: 100 percent / Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 2 h / 20 °C

5.1: 93 percent / N-methylmorpholine-N-oxide; molecular sieves 4-Angstroem / tetrapropylammonium perruthenate / CH₂Cl₂ / 1 h / 0 - 20 °C

6.1: 86 percent / tetrahydrofuran; hexane / 2 h / -10 - 20 °C

7.1: 26.2 g / K₃Fe(CN)6; K₂CO₃; Me₂SO₂NH₂ / OsO₄ / 2-methyl-propan-2-ol; H₂O; toluene / 15 h / 0 - 4 °C

8.1: 26.8 g / pyridinium p-toluenesulfonate / CH₂Cl₂ / 4 h / 20 °C

9.1: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

10.1: n-BuLi / hexamethylphosphoric acid triamide; diethyl ether; hexane / 1.5 h / -30 - -10 °C

10.2: 534 mg / hexamethylphosphoric acid triamide / 24 h / 20 °C

11.1: 73 percent / H₂ / Pd-C / ethyl acetate / 0.5 h / 20 °C

12.1: 170 mg / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.5 h / -78 - 20 °C

13.1: lithium diisopropylamide / tetrahydrofuran; hexane / 2 h / 0 °C

13.2: 347 mg / tetrahydrofuran; hexane / 2 h / 0 - 20 °C

With dmap; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; 4 A molecular sieve; Me₂SO₂NH₂; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; potassium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; potassium hexacyanoferrate(III); lithium diisopropyl amide; palladium on activated charcoal; osmium(VIII) oxide; tetrapropylammonium perruthennate; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; water; ethyl acetate; toluene; tert-butyl alcohol; 1.1: Swern oxidation / 2.1: Metallation / 2.2: Addition / 3.1: Reduction / 4.1: silylation / 5.1: Oxidation / 6.1: Wittig methylenation / 7.1: Oxidation / 8.1: Cyclization / 9.1: desilylation / 10.1: Metallation / 10.2: Alkylation / 11.1: Hydrogenation / 12.1: Swern oxidation / 13.1: Metallation / 13.2: Horner-Emmons reaction;
DOI:10.1016/S0040-4020(97)10315-5

Reference yield:

: 68654-85-3
5-(trimethylsilyl)pent-4-ynal

: 201547-38-8
t-butyl 12-benzyloxy-2-icosanyl-5-(5-spiro-2,2-dimethyl-1,3-dioxacyclopentyl)-2-dodecenoate

Guidance literature:: Multi-step reaction with 12 steps

1.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 61.6 g / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.1: 93 percent / LiAlH₄ / diethyl ether / 0 - 20 °C

3.1: 100 percent / Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 2 h / 20 °C

4.1: 93 percent / N-methylmorpholine-N-oxide; molecular sieves 4-Angstroem / tetrapropylammonium perruthenate / CH₂Cl₂ / 1 h / 0 - 20 °C

5.1: 86 percent / tetrahydrofuran; hexane / 2 h / -10 - 20 °C

6.1: 26.2 g / K₃Fe(CN)6; K₂CO₃; Me₂SO₂NH₂ / OsO₄ / 2-methyl-propan-2-ol; H₂O; toluene / 15 h / 0 - 4 °C

7.1: 26.8 g / pyridinium p-toluenesulfonate / CH₂Cl₂ / 4 h / 20 °C

8.1: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

9.1: n-BuLi / hexamethylphosphoric acid triamide; diethyl ether; hexane / 1.5 h / -30 - -10 °C

9.2: 534 mg / hexamethylphosphoric acid triamide / 24 h / 20 °C

10.1: 73 percent / H₂ / Pd-C / ethyl acetate / 0.5 h / 20 °C

11.1: 170 mg / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.5 h / -78 - 20 °C

12.1: lithium diisopropylamide / tetrahydrofuran; hexane / 2 h / 0 °C

12.2: 347 mg / tetrahydrofuran; hexane / 2 h / 0 - 20 °C

With dmap; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; 4 A molecular sieve; Me₂SO₂NH₂; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; potassium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; potassium hexacyanoferrate(III); lithium diisopropyl amide; palladium on activated charcoal; osmium(VIII) oxide; tetrapropylammonium perruthennate; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; water; ethyl acetate; toluene; tert-butyl alcohol; 1.1: Metallation / 1.2: Addition / 2.1: Reduction / 3.1: silylation / 4.1: Oxidation / 5.1: Wittig methylenation / 6.1: Oxidation / 7.1: Cyclization / 8.1: desilylation / 9.1: Metallation / 9.2: Alkylation / 10.1: Hydrogenation / 11.1: Swern oxidation / 12.1: Metallation / 12.2: Horner-Emmons reaction;
DOI:10.1016/S0040-4020(97)10315-5

Reference yield:

: 176797-93-6
7-(trimethylsilyl)hept-6-yne-1,3-diol

: 201547-38-8
t-butyl 12-benzyloxy-2-icosanyl-5-(5-spiro-2,2-dimethyl-1,3-dioxacyclopentyl)-2-dodecenoate

Guidance literature:: Multi-step reaction with 10 steps

1.1: 100 percent / Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 2 h / 20 °C

2.1: 93 percent / N-methylmorpholine-N-oxide; molecular sieves 4-Angstroem / tetrapropylammonium perruthenate / CH₂Cl₂ / 1 h / 0 - 20 °C

3.1: 86 percent / tetrahydrofuran; hexane / 2 h / -10 - 20 °C

4.1: 26.2 g / K₃Fe(CN)6; K₂CO₃; Me₂SO₂NH₂ / OsO₄ / 2-methyl-propan-2-ol; H₂O; toluene / 15 h / 0 - 4 °C

5.1: 26.8 g / pyridinium p-toluenesulfonate / CH₂Cl₂ / 4 h / 20 °C

6.1: 90 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

7.1: n-BuLi / hexamethylphosphoric acid triamide; diethyl ether; hexane / 1.5 h / -30 - -10 °C

7.2: 534 mg / hexamethylphosphoric acid triamide / 24 h / 20 °C

8.1: 73 percent / H₂ / Pd-C / ethyl acetate / 0.5 h / 20 °C

9.1: 170 mg / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.5 h / -78 - 20 °C

10.1: lithium diisopropylamide / tetrahydrofuran; hexane / 2 h / 0 °C

10.2: 347 mg / tetrahydrofuran; hexane / 2 h / 0 - 20 °C

With dmap; n-butyllithium; oxalyl dichloride; 4 A molecular sieve; Me₂SO₂NH₂; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; potassium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; potassium hexacyanoferrate(III); lithium diisopropyl amide; palladium on activated charcoal; osmium(VIII) oxide; tetrapropylammonium perruthennate; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; water; ethyl acetate; toluene; tert-butyl alcohol; 1.1: silylation / 2.1: Oxidation / 3.1: Wittig methylenation / 4.1: Oxidation / 5.1: Cyclization / 6.1: desilylation / 7.1: Metallation / 7.2: Alkylation / 8.1: Hydrogenation / 9.1: Swern oxidation / 10.1: Metallation / 10.2: Horner-Emmons reaction;
DOI:10.1016/S0040-4020(97)10315-5