ethyl 2-((1S,2S,5S,6S)-2-allyl-6-(tert-butyldimethylsilyloxy)-2-(3,4-dihydro-2H-pyrrol-5-yl)-5-methyl-3-(methanesulfonyloxy)cyclohexyl)acetate

Base Information

• Chemical Name: ethyl 2-((1S,2S,5S,6S)-2-allyl-6-(tert-butyldimethylsilyloxy)-2-(3,4-dihydro-2H-pyrrol-5-yl)-5-methyl-3-(methanesulfonyloxy)cyclohexyl)acetate
• CAS No.: 1131783-62-4
• Molecular Formula: C₂₅H₄₅NO₆SSi
• Molecular Weight: 515.787

Synonyms:ethyl 2-((1S,2S,5S,6S)-2-allyl-6-(tert-butyldimethylsilyloxy)-2-(3,4-dihydro-2H-pyrrol-5-yl)-5-methyl-3-(methanesulfonyloxy)cyclohexyl)acetate

Chemical Property of ethyl 2-((1S,2S,5S,6S)-2-allyl-6-(tert-butyldimethylsilyloxy)-2-(3,4-dihydro-2H-pyrrol-5-yl)-5-methyl-3-(methanesulfonyloxy)cyclohexyl)acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of ethyl 2-((1S,2S,5S,6S)-2-allyl-6-(tert-butyldimethylsilyloxy)-2-(3,4-dihydro-2H-pyrrol-5-yl)-5-methyl-3-(methanesulfonyloxy)cyclohexyl)acetate

There total 13 articles about ethyl 2-((1S,2S,5S,6S)-2-allyl-6-(tert-butyldimethylsilyloxy)-2-(3,4-dihydro-2H-pyrrol-5-yl)-5-methyl-3-(methanesulfonyloxy)cyclohexyl)acetate 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: 98.0%

ethyl 2-((1S,2S,5S,6S)-2-allyl-6-(tert-butyldimethylsilyloxy)-2-(3,4-dihydro-2H-pyrrol-5-yl)-3-hydroxy-5-methylcyclohexyl)acetate (1131783-60-2) + methanesulfonyl chloride (124-63-0) → ethyl 2-((1S,2S,5S,6S)-2-allyl-6-(tert-butyldimethylsilyloxy)-2-(3,4-dihydro-2H-pyrrol-5-yl)-5-methyl-3-(methanesulfonyloxy)cyclohexyl)acetate (1131783-62-4)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃;

Reference yield:

(4S,5S,E)-ethyl 4-((tert-butyldimethylsilyl)oxy)-7-hydroxy-5-methylhept-2-enoate (1131783-50-0) → ethyl 2-((1S,2S,5S,6S)-2-allyl-6-(tert-butyldimethylsilyloxy)-2-(3,4-dihydro-2H-pyrrol-5-yl)-5-methyl-3-(methanesulfonyloxy)cyclohexyl)acetate (1131783-62-4)

Guidance literature:

Multi-step reaction with 7 steps

1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere

2: sodium chlorite; 2-methyl-but-2-ene; sodium dihydrogen phosphate monohydrate / water; acetonitrile; tert-butyl alcohol / 3.5 h / 0 °C / Inert atmosphere

3: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane

4: ammonium cerium (IV) nitrate / water; acetonitrile / 0.08 h / 20 °C / Inert atmosphere

5: ammonium cerium (IV) nitrate / acetonitrile / 0 °C

6: lithium borohydride / tetrahydrofuran / -3 °C

7: triethylamine / dichloromethane / 0 - 20 °C

With sodium chlorite; lithium borohydride; ammonium cerium (IV) nitrate; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; oxalyl dichloride; Dess-Martin periodane; triethylamine; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane; water; acetonitrile; tert-butyl alcohol; 4: |Michael Addition;

DOI:10.1021/jo302333s

Reference yield:

N-(pent-4-ynyl)phthalimide (6097-07-0) → ethyl 2-((1S,2S,5S,6S)-2-allyl-6-(tert-butyldimethylsilyloxy)-2-(3,4-dihydro-2H-pyrrol-5-yl)-5-methyl-3-(methanesulfonyloxy)cyclohexyl)acetate (1131783-62-4)

Guidance literature:

Multi-step reaction with 8 steps

1: hydrazine / methanol

2: benzene / 72 h / 20 °C / Inert atmosphere; Molecular sieve

3: 2,2'-azobis(isobutyronitrile) / benzine / 85 °C

4: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane

5: ammonium cerium (IV) nitrate / water; acetonitrile / 0.08 h / 20 °C / Inert atmosphere

6: ammonium cerium (IV) nitrate / acetonitrile / 0 °C

7: lithium borohydride / tetrahydrofuran / -3 °C

8: triethylamine / dichloromethane / 0 - 20 °C

With lithium borohydride; ammonium cerium (IV) nitrate; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); triethylamine; N,N-dimethyl-formamide; hydrazine; In tetrahydrofuran; methanol; benzine; dichloromethane; water; acetonitrile; benzene; 1: |Gabriel Amine Synthesis / 5: |Michael Addition;

DOI:10.1021/jo302333s

upstream raw materials:

ethyl 2-((1S,2S,5S,6S)-2-allyl-6-(tert-butyldimethylsilyloxy)-2-(3,4-dihydro-2H-pyrrol-5-yl)-3-hydroxy-5-methylcyclohexyl)acetate

methanesulfonyl chloride

(4S,5S,E)-ethyl 4-((tert-butyldimethylsilyl)oxy)-7-hydroxy-5-methylhept-2-enoate

N-(pent-4-ynyl)phthalimide

Downstream raw materials:

ethyl 2-((1S,2S,5S,6S)-6-(tert-butyldimethylsilyloxy)-2-(3,4-dihydro-2H-pyrrol-5-yl)-2-(3-hydroxypropyl)-5-methyl-3-(methanesulfonyloxy)cyclohexyl)acetate

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