(3S,11S)-1-benzyloxy-3,11-dimethyl-14-pentadecen-7-yne

Base Information

• Chemical Name: (3S,11S)-1-benzyloxy-3,11-dimethyl-14-pentadecen-7-yne
• CAS No.: 1446944-52-0
• Molecular Formula: C₂₄H₃₆O
• Molecular Weight: 340.549
• Mol file: 1446944-52-0.mol

Synonyms:(3S,11S)-1-benzyloxy-3,11-dimethyl-14-pentadecen-7-yne

Chemical Property of (3S,11S)-1-benzyloxy-3,11-dimethyl-14-pentadecen-7-yne

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,11S)-1-benzyloxy-3,11-dimethyl-14-pentadecen-7-yne

There total 13 articles about (3S,11S)-1-benzyloxy-3,11-dimethyl-14-pentadecen-7-yne 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: 91.0%

(4R,12S)-14-benzyloxy-4,12-dimethyl-7-tetradecynal (1446944-51-9) + Methyltriphenylphosphonium bromide (1779-49-3) → (3S,11S)-1-benzyloxy-3,11-dimethyl-14-pentadecen-7-yne (1446944-52-0)

Guidance literature:

Methyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; hexane; at -50 - 20 ℃; for 4.5h; Inert atmosphere;

(4R,12S)-14-benzyloxy-4,12-dimethyl-7-tetradecynal; In tetrahydrofuran; hexane; at -65 - 20 ℃; Inert atmosphere;

DOI:10.1271/bbb.120436

Reference yield:

(S)-Citronellal (5949-05-3) → (3S,11S)-1-benzyloxy-3,11-dimethyl-14-pentadecen-7-yne (1446944-52-0)

Guidance literature:

Multi-step reaction with 11 steps

1.1: lithium aluminium tetrahydride / diethyl ether

2.1: potassium tert-butylate / dimethyl sulfoxide

3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane

4.1: periodic acid dihydrate / diethyl ether; tetrahydrofuran / 1 h / 0 - 20 °C

5.1: lithium aluminium tetrahydride / diethyl ether

6.1: pyridine

7.1: sodium iodide / N,N-dimethyl-formamide

8.1: n-butyllithium; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran

9.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane

10.1: periodic acid dihydrate / diethyl ether; tetrahydrofuran / 0 - 20 °C

11.1: n-butyllithium / hexane; tetrahydrofuran / 4.5 h / -50 - 20 °C / Inert atmosphere

11.2: -65 - 20 °C / Inert atmosphere

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; n-butyllithium; periodic acid dihydrate; potassium tert-butylate; 3-chloro-benzenecarboperoxoic acid; sodium iodide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1271/bbb.120436

Reference yield:

(S)-3,7-dimethyl-6-octen-1-ol (7540-51-4) → (3S,11S)-1-benzyloxy-3,11-dimethyl-14-pentadecen-7-yne (1446944-52-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: potassium tert-butylate / dimethyl sulfoxide

2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane

3.1: periodic acid dihydrate / diethyl ether; tetrahydrofuran / 1 h / 0 - 20 °C

4.1: lithium aluminium tetrahydride / diethyl ether

5.1: pyridine

6.1: sodium iodide / N,N-dimethyl-formamide

7.1: n-butyllithium; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran

8.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane

9.1: periodic acid dihydrate / diethyl ether; tetrahydrofuran / 0 - 20 °C

10.1: n-butyllithium / hexane; tetrahydrofuran / 4.5 h / -50 - 20 °C / Inert atmosphere

10.2: -65 - 20 °C / Inert atmosphere

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; n-butyllithium; periodic acid dihydrate; potassium tert-butylate; 3-chloro-benzenecarboperoxoic acid; sodium iodide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1271/bbb.120436

upstream raw materials:

(S)-Citronellal

(S)-((3,7-dimethyloct-6-enyloxy)methyl)benzene

(4S)-6-(benzyloxy)-4-methylhexan-1-ol

(S)-6-benzyloxy-4-methylhexyl iodide

Downstream raw materials:

(3S,11S)-3,11-dimethylpentadecyl tosylate