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

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>-1-iodo-2-methyl-2-butanol
• CAS No.: 143924-94-1
• Molecular Formula: C₃₆H₅₃IO₄Si
• Molecular Weight: 704.804
• Mol file: 143924-94-1.mol

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

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

There total 14 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>-1-iodo-2-methyl-2-butanol 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: 92.0%

(1S,2R,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 (143924-93-0,144015-92-9) → (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>-1-iodo-2-methyl-2-butanol (143924-94-1,144015-93-0)

Guidance literature:

With boron trifluoride diethyl etherate; lithium iodide; In tetrahydrofuran; at -50 ℃; for 1h;

DOI:10.1021/jo00048a009

Reference yield: 91.0%

(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 (143924-93-0,144015-92-9) → (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 (143924-94-1,144015-93-0)

Guidance literature:

With boron trifluoride diethyl etherate; lithium iodide; In tetrahydrofuran; at -50 ℃; for 1h;

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>-1-iodo-2-methyl-2-butanol (143924-94-1,144015-93-0)

Guidance literature:

Multi-step reaction with 6 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

5: 97 percent / NaH / tetrahydrofuran; paraffin / Ambient temperature

6: 91 percent / LiI, BF₃*OEt₂ / tetrahydrofuran / 1 h / -50 °C

With n-butyllithium; Amberlite IR 120 (H⁺); boron trifluoride diethyl etherate; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; lithium iodide; Lindlar's catalyst; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; paraffin;

DOI:10.1021/jo00048a009

upstream 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

(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:

(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

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

cis-(1'S,2S,5R,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