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

Base Information

• Chemical Name: 10-benzyloxy-3-(5-spiro-2,2-dimethyl-1,3-dioxacyclopentyl)-6-decyne-1-ol
• CAS No.: 201547-20-8
• Molecular Formula: C₂₁H₃₀O₄
• Molecular Weight: 346.467
• Mol file: 201547-20-8.mol

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

Chemical Property of 10-benzyloxy-3-(5-spiro-2,2-dimethyl-1,3-dioxacyclopentyl)-6-decyne-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 10-benzyloxy-3-(5-spiro-2,2-dimethyl-1,3-dioxacyclopentyl)-6-decyne-1-ol

There total 10 articles about 10-benzyloxy-3-(5-spiro-2,2-dimethyl-1,3-dioxacyclopentyl)-6-decyne-1-ol 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:

5-trimethylsilanyl-pent-4-yn-1-ol (13224-84-5) → 10-benzyloxy-3-(5-spiro-2,2-dimethyl-1,3-dioxacyclopentyl)-6-decyne-1-ol (201547-20-8)

Guidance literature:

Multi-step reaction with 10 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

With dmap; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; 4 A molecular sieve; Me₂SO₂NH₂; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; potassium hexacyanoferrate(III); lithium diisopropyl amide; osmium(VIII) oxide; tetrapropylammonium perruthennate; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; water; 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;

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

Reference yield:

5-(trimethylsilyl)pent-4-ynal (68654-85-3) → 10-benzyloxy-3-(5-spiro-2,2-dimethyl-1,3-dioxacyclopentyl)-6-decyne-1-ol (201547-20-8)

Guidance literature:

Multi-step reaction with 9 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

With dmap; lithium aluminium tetrahydride; n-butyllithium; 4 A molecular sieve; Me₂SO₂NH₂; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine; potassium hexacyanoferrate(III); lithium diisopropyl amide; osmium(VIII) oxide; tetrapropylammonium perruthennate; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; water; 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;

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

Reference yield:

7-(trimethylsilyl)hept-6-yne-1,3-diol (176797-93-6) → 10-benzyloxy-3-(5-spiro-2,2-dimethyl-1,3-dioxacyclopentyl)-6-decyne-1-ol (201547-20-8)

Guidance literature:

Multi-step reaction with 7 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

With dmap; n-butyllithium; 4 A molecular sieve; Me₂SO₂NH₂; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine; potassium hexacyanoferrate(III); osmium(VIII) oxide; tetrapropylammonium perruthennate; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; water; 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;

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

upstream raw materials:

1-[(3-bromopropoxy)methyl]-benzene

3-(5-spiro-2,2-dimethyl-1,3-dioxacyclopentyl)-6-heptyne-1-ol

5-trimethylsilanyl-pent-4-yn-1-ol

5-(trimethylsilyl)pent-4-ynal

Downstream raw materials:

[4-(7-benzyloxy-heptyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetaldehyde

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

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

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