(2R,3S,6S,8S,10R)-(E)-10-diphenyl-t-butylsiloxy-2,3-dimethyl-8-(4'-iodo-3'-methylbut-2'enyl)-1,7-dioxaspiro<5.5>undecane

Base Information

• Chemical Name: (2R,3S,6S,8S,10R)-(E)-10-diphenyl-t-butylsiloxy-2,3-dimethyl-8-(4'-iodo-3'-methylbut-2'enyl)-1,7-dioxaspiro<5.5>undecane
• CAS No.: 107692-09-1
• Molecular Formula: C₃₂H₄₅IO₃Si
• Molecular Weight: 632.697

Synonyms:(2R,3S,6S,8S,10R)-(E)-10-diphenyl-t-butylsiloxy-2,3-dimethyl-8-(4'-iodo-3'-methylbut-2'enyl)-1,7-dioxaspiro<5.5>undecane

Chemical Property of (2R,3S,6S,8S,10R)-(E)-10-diphenyl-t-butylsiloxy-2,3-dimethyl-8-(4'-iodo-3'-methylbut-2'enyl)-1,7-dioxaspiro<5.5>undecane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,6S,8S,10R)-(E)-10-diphenyl-t-butylsiloxy-2,3-dimethyl-8-(4'-iodo-3'-methylbut-2'enyl)-1,7-dioxaspiro<5.5>undecane

There total 13 articles about (2R,3S,6S,8S,10R)-(E)-10-diphenyl-t-butylsiloxy-2,3-dimethyl-8-(4'-iodo-3'-methylbut-2'enyl)-1,7-dioxaspiro<5.5>undecane 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:

Methanesulfonic acid (E)-4-[(2R,4S,6R,8R,9S)-4-(tert-butyl-diphenyl-silanyloxy)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-2-methyl-but-2-enyl ester (112995-99-0) → (2R,3S,6S,8S,10R)-(E)-10-diphenyl-t-butylsiloxy-2,3-dimethyl-8-(4'-iodo-3'-methylbut-2'enyl)-1,7-dioxaspiro<5.5>undecane (107692-09-1)

Guidance literature:

With sodium iodide; In tetrahydrofuran; Yield given;

DOI:10.1016/S0040-4039(00)84716-4

Reference yield:

(2R,3S,6S,8S,10S)-(+)-2,3-dimethyl-10-hydroxy-8-(p-tolylsulphonyloxy)methyl-1,7-dioxaspiro<5.5>undecane (107692-11-5) → (2R,3S,6S,8S,10R)-(E)-10-diphenyl-t-butylsiloxy-2,3-dimethyl-8-(4'-iodo-3'-methylbut-2'enyl)-1,7-dioxaspiro<5.5>undecane (107692-09-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 88 percent / imidazole / dimethylformamide / Ambient temperature

2: 80 percent / dimethylformamide / 12 h / 70 °C

3: di-isobutylaluminium hydride / CH₂Cl₂ / 5 h / Ambient temperature; 1.) -78 deg C --> room temp., 1 h

4: CH₂Cl₂ / 0 deg C, then room temp. overnight

5: 60 percent / di-isobutylaluminium hydride / tetrahydrofuran; diethyl ether / 1 h / -78 °C / -78 deg C --> room temp., overnight

6: triethylamine, dimethylaminopyridine / CH₂Cl₂ / 0 °C

7: sodium iodide / tetrahydrofuran / 12 h

With 1H-imidazole; dmap; diisobutylaluminum hydride; triethylamine; sodium iodide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

(2R,3S,6S,8R,10R)-(+)-10-diphenyl-t-butylsilyloxy-8-cyanomethyl-2,3-dimethyl-1,7-dioxaspiro<5.5>undecane (107692-12-6) → (2R,3S,6S,8S,10R)-(E)-10-diphenyl-t-butylsiloxy-2,3-dimethyl-8-(4'-iodo-3'-methylbut-2'enyl)-1,7-dioxaspiro<5.5>undecane (107692-09-1)

Guidance literature:

Multi-step reaction with 5 steps

1: di-isobutylaluminium hydride / CH₂Cl₂ / 5 h / Ambient temperature; 1.) -78 deg C --> room temp., 1 h

2: CH₂Cl₂ / 0 deg C, then room temp. overnight

3: 60 percent / di-isobutylaluminium hydride / tetrahydrofuran; diethyl ether / 1 h / -78 °C / -78 deg C --> room temp., overnight

4: triethylamine, dimethylaminopyridine / CH₂Cl₂ / 0 °C

5: sodium iodide / tetrahydrofuran / 12 h

With dmap; diisobutylaluminum hydride; triethylamine; sodium iodide; In tetrahydrofuran; diethyl ether; dichloromethane;

upstream raw materials:

Methanesulfonic acid (E)-4-[(2R,4S,6R,8R,9S)-4-(tert-butyl-diphenyl-silanyloxy)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-2-methyl-but-2-enyl ester

(2R,3S,6S,8S,10S)-(+)-2,3-dimethyl-10-hydroxy-8-(p-tolylsulphonyloxy)methyl-1,7-dioxaspiro<5.5>undecane

[(2S,4S,6R,8R,9S)-4-(tert-Butyl-diphenyl-silanyloxy)-8,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-acetaldehyde

(2R,3S,6S,8R,10R)-(+)-10-diphenyl-t-butylsilyloxy-8-cyanomethyl-2,3-dimethyl-1,7-dioxaspiro<5.5>undecane

Downstream raw materials:

(2R,2'R,3'S,6'S,8'R,10'R)-(+)-6-(10'-diphenyl-t-butylsiloxy-2',3'-dimethyl-1',7'-dioxaspiro<5.5>undecan-8'-yl)-2,4-dimethylhex-4-enol

(2R,3S,6S,10R)-(E)-(+)-10-diphenyl-t-butylsiloxy-8<(5'R)-3',5'-dimethyl-6'thiophenylhex-2'-enyl>-2,3-dimethyl-1,7-dioxaspiro<5.5>undecan

(2R,3S,6S,10R)-(E)-(+)-10-diphenyl-t-butylsiloxy-8<(5'R)-3',5'-dimethyl-6'-phenylsulphonylhex-2'-enyl>-2,3-dimethyl-1,7-dioxaspiro<5.5>undecan

(2R,2'R,3'S,6'S,8'R,10'R)-(+)-6-(10'-diphenyl-t-butylsiloxy-2',3'-dimethyl-1',7'-dioxaspiro<5.5>undecan-8'-yl)-2,4-dimethylhex-4-enyl toluene-p-sulphonate

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