{(1R,2S,6R)-2-(tert-butyldimethylsilyloxy)-6-[(S)-5-(tetrahydro-2H-pyran-2-yloxy)hexyl]-5-oxocyclohex-3-en-1-yl}acetaldehyde

Base Information

Chemical Name:{(1R,2S,6R)-2-(tert-butyldimethylsilyloxy)-6-[(S)-5-(tetrahydro-2H-pyran-2-yloxy)hexyl]-5-oxocyclohex-3-en-1-yl}acetaldehyde
CAS No.:882494-44-2
Molecular Formula:C₂₅H₄₄O₅Si
Molecular Weight:452.707
Hs Code.:

Synonyms:{(1R,2S,6R)-2-(tert-butyldimethylsilyloxy)-6-[(S)-5-(tetrahydro-2H-pyran-2-yloxy)hexyl]-5-oxocyclohex-3-en-1-yl}acetaldehyde

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Chemical Property of {(1R,2S,6R)-2-(tert-butyldimethylsilyloxy)-6-[(S)-5-(tetrahydro-2H-pyran-2-yloxy)hexyl]-5-oxocyclohex-3-en-1-yl}acetaldehyde

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Technology Process of {(1R,2S,6R)-2-(tert-butyldimethylsilyloxy)-6-[(S)-5-(tetrahydro-2H-pyran-2-yloxy)hexyl]-5-oxocyclohex-3-en-1-yl}acetaldehyde

There total 18 articles about {(1R,2S,6R)-2-(tert-butyldimethylsilyloxy)-6-[(S)-5-(tetrahydro-2H-pyran-2-yloxy)hexyl]-5-oxocyclohex-3-en-1-yl}acetaldehyde 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: 84.0%

: 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

: 882494-44-2
{(1R,2S,6R)-2-(tert-butyldimethylsilyloxy)-6-[(S)-5-(tetrahydro-2H-pyran-2-yloxy)hexyl]-5-oxocyclohex-3-en-1-yl}acetaldehyde

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1016/j.tet.2005.12.009

Reference yield:

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

: 882494-44-2
{(1R,2S,6R)-2-(tert-butyldimethylsilyloxy)-6-[(S)-5-(tetrahydro-2H-pyran-2-yloxy)hexyl]-5-oxocyclohex-3-en-1-yl}acetaldehyde

Guidance literature:: Multi-step reaction with 7 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

7.1: 84 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 0 °C

With 1H-imidazole; lithium aluminium tetrahydride; hydrogen fluoride; hydrogen; iodine; Dess-Martin periodane; 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:

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

: 882494-44-2
{(1R,2S,6R)-2-(tert-butyldimethylsilyloxy)-6-[(S)-5-(tetrahydro-2H-pyran-2-yloxy)hexyl]-5-oxocyclohex-3-en-1-yl}acetaldehyde

Guidance literature:: Multi-step reaction with 4 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

4.1: 84 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 0 °C

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