7-Octyn-1-ol, 8-[6-[1-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]propyl]tetrahydro-2- methoxy-3,5-dimethyl-2H-pyran-2-yl]-2-methyl-2,5-bis[(trimethylsilyl)oxy] -, 4-methylbenzenesulfonate

Base Information

• Chemical Name: 7-Octyn-1-ol, 8-[6-[1-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]propyl]tetrahydro-2- methoxy-3,5-dimethyl-2H-pyran-2-yl]-2-methyl-2,5-bis[(trimethylsilyl)oxy] -, 4-methylbenzenesulfonate
• CAS No.: 143924-91-8
• Molecular Formula: C50H78O8SSi3
• Molecular Weight: 923.487
• Mol file: 143924-91-8.mol

Synonyms:

Chemical Property of 7-Octyn-1-ol, 8-[6-[1-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]propyl]tetrahydro-2- methoxy-3,5-dimethyl-2H-pyran-2-yl]-2-methyl-2,5-bis[(trimethylsilyl)oxy] -, 4-methylbenzenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-Octyn-1-ol, 8-[6-[1-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]propyl]tetrahydro-2- methoxy-3,5-dimethyl-2H-pyran-2-yl]-2-methyl-2,5-bis[(trimethylsilyl)oxy] -, 4-methylbenzenesulfonate

There total 2 articles about 7-Octyn-1-ol, 8-[6-[1-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]propyl]tetrahydro-2- methoxy-3,5-dimethyl-2H-pyran-2-yl]-2-methyl-2,5-bis[(trimethylsilyl)oxy] -, 4-methylbenzenesulfonate 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:

(1'S,3R,5S,6S)-(+)-6-<1'-(t-butyldiphenylsilyloxymethyl)propyl>-3,5-dimethyltetrahydropyran-2-one (130514-54-4) → Toluene-4-sulfonic acid (S)-8-{(3R,5S,6S)-6-[(S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-propyl]-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl}-2-methyl-2,5-bis-trimethylsilanyloxy-oct-7-ynyl ester (143924-91-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) n-BuLi / 1.) THF, hexane, -75 deg C, 1 h, 2.) -75 deg C, 0.5 h

2: 83 mg / Amberlite IR 120 (H⁺) / 1 h

With n-butyllithium; Amberlite IR 120 (H⁺);

DOI:10.1021/jo00048a009

Reference yield:

Toluene-4-sulfonic acid (S)-2-methyl-2,5-bis-trimethylsilanyloxy-oct-7-ynyl ester (130284-43-4,137103-96-9,138290-69-4,144015-89-4,144015-90-7) → Toluene-4-sulfonic acid (S)-8-{(3R,5S,6S)-6-[(S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-propyl]-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl}-2-methyl-2,5-bis-trimethylsilanyloxy-oct-7-ynyl ester (143924-91-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) n-BuLi / 1.) THF, hexane, -75 deg C, 1 h, 2.) -75 deg C, 0.5 h

2: 83 mg / Amberlite IR 120 (H⁺) / 1 h

With n-butyllithium; Amberlite IR 120 (H⁺);

DOI:10.1021/jo00048a009

Reference yield:

Toluene-4-sulfonic acid (S)-8-{(3R,5S,6S)-6-[(S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-propyl]-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl}-2-methyl-2,5-bis-trimethylsilanyloxy-oct-7-ynyl ester (143924-91-8) → (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-2-((2S,5S,7S,9S,10S,12R)-2-iodomethyl-2,10,12-trimethyl-1,6,8-trioxa-dispiro[4.1.5.3]pentadec-13-en-9-yl)-butyl ester (143924-97-4)

Guidance literature:

Multi-step reaction with 7 steps

1: hydrogen / Lindlar catalyst / hexane; ethyl acetate / 5 h

2: PPTS / CH₂Cl₂ / 0.2 h

3: 97 percent / NaH / tetrahydrofuran; paraffin / Ambient temperature

4: 91 percent / LiI, BF₃*OEt₂ / tetrahydrofuran / 1 h / -50 °C

5: 36 percent / iodine, (diacetoxyiodo)benzene / cyclohexane / 1.5 h / 18 °C / Irradiation

6: 2.5 mg / tetra-n-butylammonium fluoride / tetrahydrofuran

7: pyridine / CCl₄ / Ambient temperature

With pyridine; [bis(acetoxy)iodo]benzene; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; iodine; pyridinium p-toluenesulfonate; sodium hydride; lithium iodide; Lindlar's catalyst; In tetrahydrofuran; tetrachloromethane; hexane; dichloromethane; cyclohexane; ethyl acetate; paraffin;

DOI:10.1021/jo00048a009

upstream raw materials:

(1'S,3R,5S,6S)-(+)-6-<1'-(t-butyldiphenylsilyloxymethyl)propyl>-3,5-dimethyltetrahydropyran-2-one

Toluene-4-sulfonic acid (S)-2-methyl-2,5-bis-trimethylsilanyloxy-oct-7-ynyl ester

Downstream raw materials:

(S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-2-((2S,5S,7S,9S,10S,12R)-2-iodomethyl-2,10,12-trimethyl-1,6,8-trioxa-dispiro[4.1.5.3]pentadec-13-en-9-yl)-butyl ester

(1S,2S,2'S,6'R,8'S,9'S,11'R)-4-<8'-<1'-<<(tert-Butyldiphenylsilyl)oxy>methyl>propyl>-9',11'-dimethyl-1',7'-dioxaspiro<5.5>undec-4'-en-2'-yl>-2-hydroxy-2-methylbutan-1-yl p-toluenesulfonate

(1S,2S,2'R,6'R,8'S,9'S,11'R)-4-<8'-<1'-<<(tert-Butyldiphenylsilyl)oxy>methyl>propyl>-9',11'-dimethyl-1',7'-dioxaspiro<5.5>undec-4'-en-2'-yl>-2-hydroxy-2-methylbutan-1-yl p-toluenesulfonate

(1S,2S,3'S,6R,8S,9S,11R)-8-<1-<<(tert-Butyldiphenylsilyl)oxy>methyl>propyl>-9,11-dimethyl-2-(3',4'-epoxy-3'-methyl-1'-butyl)-1,7-dioxaspiro<5.5>undec-4-ene