(2E,8R,10R,12E)-10-(tert-butyldimethylsilyloxy)-8-hydroxy-13-iodo-3,12-dimethyl-1-phenyltrideca-2,12-dien-6-one

Base Information

• Chemical Name: (2E,8R,10R,12E)-10-(tert-butyldimethylsilyloxy)-8-hydroxy-13-iodo-3,12-dimethyl-1-phenyltrideca-2,12-dien-6-one
• CAS No.: 1375950-75-6
• Molecular Formula: C₂₇H₄₃IO₃Si
• Molecular Weight: 570.627

Synonyms:(2E,8R,10R,12E)-10-(tert-butyldimethylsilyloxy)-8-hydroxy-13-iodo-3,12-dimethyl-1-phenyltrideca-2,12-dien-6-one

Chemical Property of (2E,8R,10R,12E)-10-(tert-butyldimethylsilyloxy)-8-hydroxy-13-iodo-3,12-dimethyl-1-phenyltrideca-2,12-dien-6-one

Chemical Property:

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Technology Process of (2E,8R,10R,12E)-10-(tert-butyldimethylsilyloxy)-8-hydroxy-13-iodo-3,12-dimethyl-1-phenyltrideca-2,12-dien-6-one

There total 9 articles about (2E,8R,10R,12E)-10-(tert-butyldimethylsilyloxy)-8-hydroxy-13-iodo-3,12-dimethyl-1-phenyltrideca-2,12-dien-6-one 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: 66.0%

(E)-5-methyl-7-phenylhept-5-en-2-one (1375950-76-7) + (R,E)-3-(tert-butyldimethylsilyloxy)-6-iodo-5-methylhex-5-enal (1375950-77-8) → (2E,8S,10R,12E)-10-(tert-butyldimethylsilyloxy)-8-hydroxy-13-iodo-3,12-dimethyl-1-phenyltrideca-2,12-dien-6-one (1375950-89-2) + (2E,8R,10R,12E)-10-(tert-butyldimethylsilyloxy)-8-hydroxy-13-iodo-3,12-dimethyl-1-phenyltrideca-2,12-dien-6-one (1375950-75-6)

Guidance literature:

(E)-5-methyl-7-phenylhept-5-en-2-one; With triethylamine; B-chlorodiisopinocampheylborane; In diethyl ether; at -78 - 0 ℃; for 1.5h; Inert atmosphere;

(R,E)-3-(tert-butyldimethylsilyloxy)-6-iodo-5-methylhex-5-enal; In diethyl ether; at -78 - 0 ℃; Inert atmosphere;

With dihydrogen peroxide; In methanol; diethyl ether; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/ol302219x

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (2E,8S,10R,12E)-10-(tert-butyldimethylsilyloxy)-8-hydroxy-13-iodo-3,12-dimethyl-1-phenyltrideca-2,12-dien-6-one (1375950-89-2) + (2E,8R,10R,12E)-10-(tert-butyldimethylsilyloxy)-8-hydroxy-13-iodo-3,12-dimethyl-1-phenyltrideca-2,12-dien-6-one (1375950-75-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / -30 °C

2.1: potassium carbonate / tetrahydrofuran; methanol / 20 h / 0 - 20 °C

3.1: zirconocene dichloride / dichloromethane; toluene / 2.5 h / 0 - 20 °C / Inert atmosphere

3.2: 1 h / -50 °C / Inert atmosphere

4.1: asymmetric dihydroxylation-mix-β / water; tert-butyl alcohol / 15 h / 0 °C

5.1: sodium periodate / methanol; water / 0.57 h / 0 - 20 °C

6.1: (+)-β-chlorodiisopinocampheylborane; triethylamine / diethyl ether / 1 h / -78 - 0 °C / Inert atmosphere

6.2: 16.5 h / -78 - -20 °C / Inert atmosphere

With 2,6-dimethylpyridine; sodium periodate; zirconocene dichloride; (+)-β-chlorodiisopinocampheylborane; asymmetric dihydroxylation-mix-β; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; tert-butyl alcohol; 4.1: Sharpless dihydroxylation / 6.2: Paterson aldol reaction;

DOI:10.1002/anie.201108749

Reference yield:

benzyl bromide (100-39-0) → (2E,8S,10R,12E)-10-(tert-butyldimethylsilyloxy)-8-hydroxy-13-iodo-3,12-dimethyl-1-phenyltrideca-2,12-dien-6-one (1375950-89-2) + (2E,8R,10R,12E)-10-(tert-butyldimethylsilyloxy)-8-hydroxy-13-iodo-3,12-dimethyl-1-phenyltrideca-2,12-dien-6-one (1375950-75-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: zirconocene dichloride / dichloromethane; toluene / 3 h / 0 - 20 °C / Inert atmosphere

1.2: 18 h / 0 °C / Inert atmosphere

2.1: tert.-butyl lithium / tetrahydrofuran; diethyl ether / -78 - 20 °C

3.1: (+)-β-chlorodiisopinocampheylborane; triethylamine / diethyl ether / 1 h / -78 - 0 °C / Inert atmosphere

3.2: 16.5 h / -78 - -20 °C / Inert atmosphere

With zirconocene dichloride; (+)-β-chlorodiisopinocampheylborane; tert.-butyl lithium; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 3.2: Paterson aldol reaction;

DOI:10.1002/anie.201108749

upstream raw materials:

C₁₆H₃₂OSi₂

((S)-hept-1-en-6-yn-4-yloxy)(tert-butyl)dimethylsilane

((S,E)-1-iodo-2-methylhepta-1,6-dien-4-yloxy)(tert-butyl)dimethylsilane

(E)-5-methyl-7-phenylhept-5-en-2-one

Downstream raw materials:

(3E,6E,9E,12R,14S)-12-((tert-butyldimethylsilyl)oxy)-14-((R,E)-2-((tert-butyldimethylsilyl)oxy)-5-methyl-7-phenylhept-5-en-1-yl)-4-(2-hydroxyethyl)-10-methyloxacyclotetradeca-3,6,9-trien-2-one

(Z)-((5R,7S,9R)-5-((E)-3-iodo-2-methylallyl)-2,2,3,3,11,11,12,12-octamethyl-9-((E)-3-methyl-5-phenylpent-3-enyl)-4,10-dioxa-3,11-disilatridecan-7-yl) 5-(tert-butyldimethylsilyloxy)-3-iodopent-2-enoate

(E)-(5R,7S,9R)-2,2,3,3,11,11,12,12-octamethyl-5-((E)-3-methyl-5-phenylpent-3-en-1-yl)-9-((E)-2-methylhexa-2,5-dien-1-yl)-4,10-dioxa-3,11-disilatridecan-7-yl 3-(2-((tert-butyldimethylsilyl)oxy)ethyl)hexa-2,5-dienoate

(5R,7S,9R)-5-((E)-3-iodo-2-methylallyl)-2,2,3,3,11,11,12,12-octamethyl-9-((E)-3-methyl-5-phenylpent-3-enyl)-4,10-dioxa-3,11-disilatridecan-7-yl acetate

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