(3R,6R,7S)-3-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-6-methyl-6-((triethylsilyl)oxy)non-8-enoic acid

Base Information

• Chemical Name: (3R,6R,7S)-3-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-6-methyl-6-((triethylsilyl)oxy)non-8-enoic acid
• CAS No.: 1399679-73-2
• Molecular Formula: C₃₀H₅₄O₆Si₂
• Molecular Weight: 566.926

Synonyms:(3R,6R,7S)-3-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-6-methyl-6-((triethylsilyl)oxy)non-8-enoic acid

Chemical Property of (3R,6R,7S)-3-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-6-methyl-6-((triethylsilyl)oxy)non-8-enoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (3R,6R,7S)-3-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-6-methyl-6-((triethylsilyl)oxy)non-8-enoic acid

There total 10 articles about (3R,6R,7S)-3-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-6-methyl-6-((triethylsilyl)oxy)non-8-enoic acid 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: 96.0%

(3R,6R,7S)-tert-butyl 3-((tert-butyldimethylsilyl)oxy)-6-hydroxy-7-((4-methoxybenzyl)oxy)-6-methylnon-8-enoate (1399679-86-7) + triethylsilyl trifluoromethyl sulfonate (79271-56-0) → (3R,6R,7S)-3-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-6-methyl-6-((triethylsilyl)oxy)non-8-enoic acid (1399679-73-2)

Guidance literature:

(3R,6R,7S)-tert-butyl 3-((tert-butyldimethylsilyl)oxy)-6-hydroxy-7-((4-methoxybenzyl)oxy)-6-methylnon-8-enoate; triethylsilyl trifluoromethyl sulfonate; With triethylamine; In dichloromethane; at 0 ℃; for 2h; Inert atmosphere;

With hydrogenchloride; In dichloromethane; water; Inert atmosphere;

DOI:10.1021/ol301886g

Reference yield:

(6R,7S)-tert-butyl 6-hydroxy-7-((4-methoxybenzyl)oxy)-3-oxonon-8-enoate (1399680-18-2) → (3R,6R,7S)-3-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-6-methyl-6-((triethylsilyl)oxy)non-8-enoic acid (1399679-73-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 1H-imidazole / dichloromethane / 4 h / 0 - 23 °C / Inert atmosphere

2.1: sodium tetrahydroborate / tetrahydrofuran / -20 °C

3.1: 1H-imidazole; dmap / dichloromethane / Inert atmosphere

4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; dimethyl sulfoxide / tetrahydrofuran / 36 h / 23 °C / Inert atmosphere

5.1: tetrahydrofuran; diethyl ether / 2 h / -78 - -40 °C / Inert atmosphere

6.1: triethylamine / dichloromethane / 2 h / 0 °C / Inert atmosphere

6.2: Inert atmosphere

With 1H-imidazole; dmap; sodium tetrahydroborate; dimethyl sulfoxide; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/ol301886g

Reference yield:

4-Methoxybenzyl alcohol (105-13-5) → (3R,6R,7S)-3-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-6-methyl-6-((triethylsilyl)oxy)non-8-enoic acid (1399679-73-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: phosphorus tribromide / diethyl ether / 2 h / 0 °C

2.1: sodium hydride; tetra-(n-butyl)ammonium iodide / tetrahydrofuran; mineral oil / 0 - 23 °C / Inert atmosphere

3.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

3.2: Inert atmosphere

4.1: 1H-imidazole / dichloromethane / 4 h / 0 - 23 °C / Inert atmosphere

5.1: sodium tetrahydroborate / tetrahydrofuran / -20 °C

6.1: 1H-imidazole; dmap / dichloromethane / Inert atmosphere

7.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; dimethyl sulfoxide / tetrahydrofuran / 36 h / 23 °C / Inert atmosphere

8.1: tetrahydrofuran; diethyl ether / 2 h / -78 - -40 °C / Inert atmosphere

9.1: triethylamine / dichloromethane / 2 h / 0 °C / Inert atmosphere

9.2: Inert atmosphere

With 1H-imidazole; dmap; sodium tetrahydroborate; phosphorus tribromide; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; diethyl ether; dichloromethane; mineral oil;

DOI:10.1021/ol301886g

upstream raw materials:

4-Methoxybenzyl alcohol

(6R,7S)-tert-butyl 6-hydroxy-7-((4-methoxybenzyl)oxy)-3-oxonon-8-enoate

(6R,7S)-tert-butyl 7-((4-methoxybenzyl)oxy)-3-oxo-6-((triethylsilyl)oxy)non-8-enoate

divinylcarbinol

Downstream raw materials:

(3R,6R,7S)-(3S,4S,E)-3,5-dimethyl-7-(trityloxy)hepta-1,5-dien-4-yl 3-((tert-butyldimethylsilyl)oxy)-7-((4-methoxybenzyl)oxy)-6-methyl-6-((triethylsilyl)oxy)non-8-enoate

(3R,6R,7S)-(3S,4S,E)-3,5-dimethyl-7-(trityloxy)hepta-1,5-dien-4-yl-3-((tert-butyldimethylsilyl)oxy)-7-hydroxy-6-methyl-6-((triethylsilyl)oxy)non-8-enoate

(4R,7R,8S,11R,12R,E)-4-((tert-butyldimethylsilyl)oxy)-8-hydroxy-7,11-dimethyl-7-((triethylsilyl)oxy)-12-((E)-4-(trityloxy)but-2-en-2-yl)oxacyclododec-9-en-2-one

(E)-4-((tert-butyldimethylsilyl)oxy)-8-hydroxy-7,11-dimethyl-7-((triethylsilyl)oxy)-12-((E)-4-(trityloxy)but-2-en-2-yl)oxacyclododec-9-en-2-one

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