5-Heptyn-1-ol, 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, (2S)-

Base Information

• Chemical Name: 5-Heptyn-1-ol, 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, (2S)-
• CAS No.: 268736-73-8
• Molecular Formula: C13H26O2Si
• Molecular Weight: 242.434
• Mol file: 268736-73-8.mol

Synonyms:

Chemical Property of 5-Heptyn-1-ol, 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, (2S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-Heptyn-1-ol, 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, (2S)-

There total 1 articles about 5-Heptyn-1-ol, 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, (2S)- 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:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran (32780-06-6) → 2-(tert-butyl-dimethyl-silanyloxy)-hept-5-yn-1-ol (268736-73-8)

Guidance literature:

Multi-step reaction with 5 steps

1: N-ethyl-N,N-diisopropylamine / dichloromethane / 12 h / Inert atmosphere; Reflux

2: triphenylphosphine / tetrahydrofuran / 4 h / Reflux; Inert atmosphere

3: 1,2-diamino-benzene; iron(III)-acetylacetonate / diethyl ether / 1.5 h / 0 - 20 °C / Inert atmosphere

4: 2,6-dimethylpyridine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

5: dimethylboron bromide / dichloromethane / 1.5 h / -78 °C / Inert atmosphere

With 2,6-dimethylpyridine; iron(III)-acetylacetonate; dimethylboron bromide; N-ethyl-N,N-diisopropylamine; 1,2-diamino-benzene; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; 2: |Wittig Olefination;

DOI:10.1002/chem.201404873

Reference yield:

2-(tert-butyl-dimethyl-silanyloxy)-hept-5-yn-1-ol (268736-73-8) → (2S,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-benzyloxy)-4-methoxy-dec-8-ynal (400736-32-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 90 percent / TPAP; NMO; molecular sieves / CH₂Cl₂ / 2 h / 0 - 25 °C

2.1: diethyl ether / 1 h / -100 °C

2.2: 85 percent / NaBO₃*4H₂O / tetrahydrofuran; H₂O / 12 h / 25 °C

3.1: 85 percent / 2,6-di-tert-butyl-4-methyl pyridine / CH₂Cl₂ / 24 h / 40 °C

4.1: 85 percent / K₃[Fe(CN)6]; K₂CO₃; (DHQ)2*PYR / OsO₄ / 2-methyl-propan-2-ol; H₂O / 12 h / 0 °C

5.1: 99 percent / CSA / toluene / 12 h / 110 °C

6.1: 70 percent / DIBAL-H / CH₂Cl₂ / 0.5 h / -78 °C

7.1: 95 percent / SO₃*py; Et₃N / dimethylsulfoxide; CH₂Cl₂ / 0.5 h / 0 - 25 °C

With N-methyl-2-indolinone; 2,6-di-tert-butyl-4-methylpyridine; molecular sieve; tetrapropylammonium perruthennate; (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); pyridine-SO₃ complex; camphor-10-sulfonic acid; diisobutylaluminium hydride; potassium carbonate; triethylamine; potassium hexacyanoferrate(III); osmium(VIII) oxide; In diethyl ether; dichloromethane; water; dimethyl sulfoxide; toluene; tert-butyl alcohol;

DOI:10.1002/1521-3773(20011015)40:20<3849::AID-ANIE3849>3.0.CO;2-M

Reference yield:

2-(tert-butyl-dimethyl-silanyloxy)-hept-5-yn-1-ol (268736-73-8) → tert-Butyl-((S)-1-{(S)-2-[(S)-2-(3,4-dimethoxy-phenyl)-[1,3]dioxolan-4-yl]-1-methoxy-ethyl}-hex-4-ynyloxy)-dimethyl-silane (400737-13-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 90 percent / TPAP; NMO; molecular sieves / CH₂Cl₂ / 2 h / 0 - 25 °C

2.1: diethyl ether / 1 h / -100 °C

2.2: 85 percent / NaBO₃*4H₂O / tetrahydrofuran; H₂O / 12 h / 25 °C

3.1: 85 percent / 2,6-di-tert-butyl-4-methyl pyridine / CH₂Cl₂ / 24 h / 40 °C

4.1: 85 percent / K₃[Fe(CN)6]; K₂CO₃; (DHQ)2*PYR / OsO₄ / 2-methyl-propan-2-ol; H₂O / 12 h / 0 °C

5.1: 99 percent / CSA / toluene / 12 h / 110 °C

With N-methyl-2-indolinone; 2,6-di-tert-butyl-4-methylpyridine; molecular sieve; tetrapropylammonium perruthennate; (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); camphor-10-sulfonic acid; potassium carbonate; potassium hexacyanoferrate(III); osmium(VIII) oxide; In diethyl ether; dichloromethane; water; toluene; tert-butyl alcohol;

DOI:10.1002/1521-3773(20011015)40:20<3849::AID-ANIE3849>3.0.CO;2-M

upstream raw materials:

(5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran

Downstream raw materials:

(2S,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-benzyloxy)-4-methoxy-dec-8-ynal

tert-Butyl-((S)-1-{(S)-2-[(S)-2-(3,4-dimethoxy-phenyl)-[1,3]dioxolan-4-yl]-1-methoxy-ethyl}-hex-4-ynyloxy)-dimethyl-silane

(2S,4S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-benzyloxy)-4-methoxy-dec-8-yn-1-ol