((E)-((2R,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-vinylcyclohexylidene)methoxy)triisopropylsilane

Base Information

• Chemical Name: ((E)-((2R,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-vinylcyclohexylidene)methoxy)triisopropylsilane
• CAS No.: 1392307-56-0
• Molecular Formula: C₃₂H₅₆O₃Si₂
• Molecular Weight: 544.966

Synonyms:((E)-((2R,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-vinylcyclohexylidene)methoxy)triisopropylsilane

Chemical Property of ((E)-((2R,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-vinylcyclohexylidene)methoxy)triisopropylsilane

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of ((E)-((2R,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-vinylcyclohexylidene)methoxy)triisopropylsilane

There total 15 articles about ((E)-((2R,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-vinylcyclohexylidene)methoxy)triisopropylsilane 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: 99.0%

(2R,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-vinylcyclohexanecarbaldehyde (1392307-55-9) + triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → ((E)-((2R,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-vinylcyclohexylidene)methoxy)triisopropylsilane (1392307-56-0)

Guidance literature:

With triethylamine; In dichloromethane; at 50 ℃; for 1h; Inert atmosphere;

DOI:10.1002/anie.201108223

Reference yield:

(S)-4-benzyl-3-((2S,3R,4R)-2-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-7-enoyl)oxazolidin-2-one → ((E)-((2R,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-vinylcyclohexylidene)methoxy)triisopropylsilane (1392307-56-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: sodium tetrahydroborate / tetrahydrofuran; water / 0 - 20 °C

2.1: Dess-Martin periodane / dichloromethane / 2.5 h / 20 °C

3.1: dichloromethane / 20 h

4.1: diisobutylaluminium hydride / diethyl ether; toluene / -40 °C / Inert atmosphere

5.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.25 h / Cooling with ice

6.2: 0.25 h

7.1: pyrrolidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

8.1: triethylamine / dichloromethane / 1 h / 50 °C / Inert atmosphere

With pyrrolidine; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; carbon tetrabromide; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; water; toluene; 2.1: Dess-Martin oxidation / 3.1: Wittig reaction / 7.1: Tsuji-Trost cyclization;

DOI:10.1002/anie.201108223

Reference yield:

(2R,3R,4R)-2-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-7-en-1-ol (1392307-50-4) → ((E)-((2R,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-vinylcyclohexylidene)methoxy)triisopropylsilane (1392307-56-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: Dess-Martin periodane / dichloromethane / 2.5 h / 20 °C

2.1: dichloromethane / 20 h

3.1: diisobutylaluminium hydride / diethyl ether; toluene / -40 °C / Inert atmosphere

4.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.25 h / Cooling with ice

5.2: 0.25 h

6.1: pyrrolidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

7.1: triethylamine / dichloromethane / 1 h / 50 °C / Inert atmosphere

With pyrrolidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; carbon tetrabromide; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 1.1: Dess-Martin oxidation / 2.1: Wittig reaction / 6.1: Tsuji-Trost cyclization;

DOI:10.1002/anie.201108223

upstream raw materials:

(2R,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-vinylcyclohexanecarbaldehyde

triisopropylsilyl trifluoromethanesulfonate

(2R,3R,4R)-2-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-7-en-1-ol

(4R,5R,6R,(E))-ethyl 4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-6,10-dimethylundeca-2,9-dienoate

Downstream raw materials:

(2S,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-vinylcyclohexanone

ethyl 3-(1R,2S,3R,4R,5R)-3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-1-hydroxy-5-methyl-2-(vinylcyclohexyl)propiolate

(1R,2S,3R,4R,5R)-3-(benzyloxy)-4-(tertbutyldimethylsilyloxy)-5-methyl-1-(3,3,3-triethoxyprop-1-ynyl)-2-vinylcyclohexanol

ethyl 3-((1R,2S,3R,4R,5R)-3-(benzyloxy)-1,4-dihydroxy-5-methyl-2-vinylcyclohexyl)propiolate

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