(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

Base Information

• Chemical Name: (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
• CAS No.: 143924-92-9
• Molecular Formula: C₄₃H₆₀O₇SSi
• Molecular Weight: 749.097

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 10 articles about (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 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) → (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 (143924-92-9,144015-91-8)

Guidance literature:

Multi-step reaction with 4 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

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

4: PPTS / CH₂Cl₂ / 0.2 h

With n-butyllithium; Amberlite IR 120 (H⁺); hydrogen; pyridinium p-toluenesulfonate; Lindlar's catalyst; In hexane; dichloromethane; ethyl acetate;

DOI:10.1021/jo00048a009

Reference yield:

(1'S,3R,5S,6S)-(+)-6-<1'-(t-butyldiphenylsilyloxymethyl)propyl>-3,5-dimethyltetrahydropyran-2-one (130514-54-4) → (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 (143924-92-9,144015-91-8)

Guidance literature:

Multi-step reaction with 4 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

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

4: PPTS / CH₂Cl₂ / 0.2 h

With n-butyllithium; Amberlite IR 120 (H⁺); hydrogen; pyridinium p-toluenesulfonate; Lindlar's catalyst; In hexane; dichloromethane; ethyl acetate;

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) → (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 (143924-92-9,144015-91-8)

Guidance literature:

Multi-step reaction with 4 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

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

4: PPTS / CH₂Cl₂ / 0.2 h

With n-butyllithium; Amberlite IR 120 (H⁺); hydrogen; pyridinium p-toluenesulfonate; Lindlar's catalyst; In hexane; dichloromethane; ethyl acetate;

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

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

Downstream raw materials:

(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

(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>-1-iodo-2-methyl-2-butanol

trans-(1'S,2S,5S,7S,9S,10S,12R)-9-<1'-<<(tert-Butyldiphenylsilyl)oxy>methyl>propyl>-2-(iodomethyl)-2,10,12-trimethyl-1,6,8-trioxadispiro<4.1.5.3>pentadec-13-ene

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