10-benzyloxy-3-(5-spiro-2,2-dimethyl-1,3-dioxacyclopentyl)-1-decanol

Base Information

Chemical Name:10-benzyloxy-3-(5-spiro-2,2-dimethyl-1,3-dioxacyclopentyl)-1-decanol
CAS No.:201547-21-9
Molecular Formula:C₂₁H₃₄O₄
Molecular Weight:350.499
Hs Code.:

Synonyms:10-benzyloxy-3-(5-spiro-2,2-dimethyl-1,3-dioxacyclopentyl)-1-decanol

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Chemical Property of 10-benzyloxy-3-(5-spiro-2,2-dimethyl-1,3-dioxacyclopentyl)-1-decanol

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Technology Process of 10-benzyloxy-3-(5-spiro-2,2-dimethyl-1,3-dioxacyclopentyl)-1-decanol

There total 11 articles about 10-benzyloxy-3-(5-spiro-2,2-dimethyl-1,3-dioxacyclopentyl)-1-decanol 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: 73.0%

: 201547-20-8
10-benzyloxy-3-(5-spiro-2,2-dimethyl-1,3-dioxacyclopentyl)-6-decyne-1-ol

: 201547-21-9
10-benzyloxy-3-(5-spiro-2,2-dimethyl-1,3-dioxacyclopentyl)-1-decanol

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethyl acetate; at 20 ℃; for 0.5h;
DOI:10.1016/S0040-4020(97)10315-5

Reference yield:

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

: 201547-21-9
10-benzyloxy-3-(5-spiro-2,2-dimethyl-1,3-dioxacyclopentyl)-1-decanol

Guidance literature:: Multi-step reaction with 11 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

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;
DOI:10.1016/S0040-4020(97)10315-5

Reference yield:

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

: 201547-21-9
10-benzyloxy-3-(5-spiro-2,2-dimethyl-1,3-dioxacyclopentyl)-1-decanol

Guidance literature:: Multi-step reaction with 10 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

With dmap; lithium aluminium tetrahydride; n-butyllithium; 4 A molecular sieve; Me₂SO₂NH₂; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; potassium carbonate; 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;
DOI:10.1016/S0040-4020(97)10315-5