(4S,5R,6R)-4-(tert-butyldimethylsilyloxy)-5-(2-hydroxyethyl)-6-[(S)-5-(tetrahydro-2H-pyran-2-yloxy)hexyl]cyclohex-2-en-1-one

Base Information

Chemical Name:(4S,5R,6R)-4-(tert-butyldimethylsilyloxy)-5-(2-hydroxyethyl)-6-[(S)-5-(tetrahydro-2H-pyran-2-yloxy)hexyl]cyclohex-2-en-1-one
CAS No.:882494-43-1
Molecular Formula:C₂₅H₄₆O₅Si
Molecular Weight:454.723
Hs Code.:

Synonyms:(4S,5R,6R)-4-(tert-butyldimethylsilyloxy)-5-(2-hydroxyethyl)-6-[(S)-5-(tetrahydro-2H-pyran-2-yloxy)hexyl]cyclohex-2-en-1-one

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Chemical Property of (4S,5R,6R)-4-(tert-butyldimethylsilyloxy)-5-(2-hydroxyethyl)-6-[(S)-5-(tetrahydro-2H-pyran-2-yloxy)hexyl]cyclohex-2-en-1-one

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Technology Process of (4S,5R,6R)-4-(tert-butyldimethylsilyloxy)-5-(2-hydroxyethyl)-6-[(S)-5-(tetrahydro-2H-pyran-2-yloxy)hexyl]cyclohex-2-en-1-one

There total 16 articles about (4S,5R,6R)-4-(tert-butyldimethylsilyloxy)-5-(2-hydroxyethyl)-6-[(S)-5-(tetrahydro-2H-pyran-2-yloxy)hexyl]cyclohex-2-en-1-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:

: (E)-(S)-5-(Tetrahydro-pyran-2-yloxy)-hex-2-enoic acid ethyl ester

: 882494-43-1
(4S,5R,6R)-4-(tert-butyldimethylsilyloxy)-5-(2-hydroxyethyl)-6-[(S)-5-(tetrahydro-2H-pyran-2-yloxy)hexyl]cyclohex-2-en-1-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 95 percent / H₂ / Pd/C / ethyl acetate / 5 h / 20 °C

2.1: 98 percent / LiAlH₄ / diethyl ether / 1 h / 0 °C

3.1: 87 percent / imidazole; PPh₃; iodine / CH₂Cl₂ / 3 h / 20 °C

4.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.08 h / -60 °C

4.2: tetrahydrofuran; hexane / 0.5 h / -60 °C

5.1: 354 mg / CaCO₃ / toluene / 2 h / 100 °C

6.1: 98 percent / HF / acetonitrile / 0.25 h / 20 °C

With 1H-imidazole; lithium aluminium tetrahydride; hydrogen fluoride; hydrogen; iodine; triphenylphosphine; calcium carbonate; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; ethyl acetate; toluene; acetonitrile;
DOI:10.1016/j.tet.2005.12.009

Reference yield:

: 882494-31-7
(S)-5-(tetrahydro-2H-pyran-2-yloxy)hexan-1-ol

: 882494-43-1
(4S,5R,6R)-4-(tert-butyldimethylsilyloxy)-5-(2-hydroxyethyl)-6-[(S)-5-(tetrahydro-2H-pyran-2-yloxy)hexyl]cyclohex-2-en-1-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 87 percent / imidazole; PPh₃; iodine / CH₂Cl₂ / 3 h / 20 °C

2.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.08 h / -60 °C

2.2: tetrahydrofuran; hexane / 0.5 h / -60 °C

3.1: 354 mg / CaCO₃ / toluene / 2 h / 100 °C

4.1: 98 percent / HF / acetonitrile / 0.25 h / 20 °C

With 1H-imidazole; hydrogen fluoride; iodine; triphenylphosphine; calcium carbonate; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; toluene; acetonitrile;
DOI:10.1016/j.tet.2005.12.009

Reference yield:

: 882494-32-8
(S)-1-iodo-5-(tetrahydro-2H-pyran-2-yloxy)hexane

: 882494-43-1
(4S,5R,6R)-4-(tert-butyldimethylsilyloxy)-5-(2-hydroxyethyl)-6-[(S)-5-(tetrahydro-2H-pyran-2-yloxy)hexyl]cyclohex-2-en-1-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium diisopropylamide / tetrahydrofuran; hexane / 0.08 h / -60 °C

1.2: tetrahydrofuran; hexane / 0.5 h / -60 °C

2.1: 354 mg / CaCO₃ / toluene / 2 h / 100 °C

3.1: 98 percent / HF / acetonitrile / 0.25 h / 20 °C

With hydrogen fluoride; calcium carbonate; lithium diisopropyl amide; In tetrahydrofuran; hexane; toluene; acetonitrile;
DOI:10.1016/j.tet.2005.12.009