<3S-(3α,5α,6β)>-5-<(tert-Butyldimethylsilyl)oxy>tetrahydro-6-(cyclohexylmethyl)-3-isopropyl-2H-pyran-2-one

Base Information

• Chemical Name: <3S-(3α,5α,6β)>-5-<(tert-Butyldimethylsilyl)oxy>tetrahydro-6-(cyclohexylmethyl)-3-isopropyl-2H-pyran-2-one
• CAS No.: 125816-08-2
• Molecular Formula: C₂₁H₄₀O₃Si
• Molecular Weight: 368.632

Synonyms:<3S-(3α,5α,6β)>-5-<(tert-Butyldimethylsilyl)oxy>tetrahydro-6-(cyclohexylmethyl)-3-isopropyl-2H-pyran-2-one

Chemical Property of <3S-(3α,5α,6β)>-5-<(tert-Butyldimethylsilyl)oxy>tetrahydro-6-(cyclohexylmethyl)-3-isopropyl-2H-pyran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <3S-(3α,5α,6β)>-5-<(tert-Butyldimethylsilyl)oxy>tetrahydro-6-(cyclohexylmethyl)-3-isopropyl-2H-pyran-2-one

There total 17 articles about <3S-(3α,5α,6β)>-5-<(tert-Butyldimethylsilyl)oxy>tetrahydro-6-(cyclohexylmethyl)-3-isopropyl-2H-pyran-2-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:

<5S-(5α,6β)>-5-<(tert-Butyldimethylsilyl)oxy>-6-(cyclohexylidenemethyl)-5,6-dihydro-2H-pyran-2-one (130316-22-2) → <3S-(3α,5α,6β)>-5-<(tert-Butyldimethylsilyl)oxy>tetrahydro-6-(cyclohexylmethyl)-3-isopropyl-2H-pyran-2-one (125816-08-2)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂ / 10percent Pd/C / ethyl acetate / 760 Torr

2: LiN(TMS)2 / tetrahydrofuran / 0.17 h / -78 °C

3: pyridine

4: 1.) DBN / 1.) THF, 25 deg C, 2.) THF, -78 deg C, 10 min,

5: LiN(TMS)2 / 0.08 h / -78 °C

With 2,6-dichloro-benzonitrile; hydrogen; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; pyridine; ethyl acetate;

DOI:10.1016/S0040-4039(01)80478-0

Reference yield:

Ethyl 4-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enodialdopyranoside-(1,5) (112571-70-7) → <3S-(3α,5α,6β)>-5-<(tert-Butyldimethylsilyl)oxy>tetrahydro-6-(cyclohexylmethyl)-3-isopropyl-2H-pyran-2-one (125816-08-2)

Guidance literature:

Multi-step reaction with 7 steps

1: tetrahydrofuran / 1.5 h / 25 °C

2: CrO₃, H₂SO₄ / acetone / 0.17 h / 0 °C

3: H₂ / 10percent Pd/C / ethyl acetate / 760 Torr

4: LiN(TMS)2 / tetrahydrofuran / 0.17 h / -78 °C

5: pyridine

6: 1.) DBN / 1.) THF, 25 deg C, 2.) THF, -78 deg C, 10 min,

7: LiN(TMS)2 / 0.08 h / -78 °C

With chromium(VI) oxide; 2,6-dichloro-benzonitrile; sulfuric acid; hydrogen; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; pyridine; ethyl acetate; acetone;

DOI:10.1016/S0040-4039(01)80478-0

Reference yield:

Ethyl 4-O-(tert-butyldimethylsilyl)-6-cyclohexylidene-2,3,6-trideoxy-α-D-erythro-hex-2-enoaldopyranoside-(1,5) (130335-92-1) → <3S-(3α,5α,6β)>-5-<(tert-Butyldimethylsilyl)oxy>tetrahydro-6-(cyclohexylmethyl)-3-isopropyl-2H-pyran-2-one (125816-08-2)

Guidance literature:

Multi-step reaction with 6 steps

1: CrO₃, H₂SO₄ / acetone / 0.17 h / 0 °C

2: H₂ / 10percent Pd/C / ethyl acetate / 760 Torr

3: LiN(TMS)2 / tetrahydrofuran / 0.17 h / -78 °C

4: pyridine

5: 1.) DBN / 1.) THF, 25 deg C, 2.) THF, -78 deg C, 10 min,

6: LiN(TMS)2 / 0.08 h / -78 °C

With chromium(VI) oxide; 2,6-dichloro-benzonitrile; sulfuric acid; hydrogen; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; pyridine; ethyl acetate; acetone;

DOI:10.1016/S0040-4039(01)80478-0

upstream raw materials:

lithium dimethylcuprate

Methanesulfonic acid 1-[(5S,6R)-5-(tert-butyl-dimethyl-silanyloxy)-6-cyclohexylmethyl-2-oxo-tetrahydro-pyran-3-yl]-ethyl ester

methyllithium

<5S-(5α,6β),3(E)>-5-<(tert-Butyldimethylsilyl)oxy>tetrahydro-6-(cyclohexylmethyl)-3-ethylidene-2H-pyran-2-one

Downstream raw materials:

<3S-<3α,5β(S^*)>>-5-(2-Cyclohexyl-1-hydroxyethyl)dihydro-3-isopropyl-2(3H)-furanone

<3R-(3α,5β,6α)>-5-<(tert-Butyldimethylsilyl)oxy>tetrahydro-6-(cyclohexylmethyl)-3-isopropyl-2H-pyran-2-one

<3S-<3α,5β(R^*)>>-5-(2-Cyclohexyl-1-aminoethyl)dihydro-3-isopropyl-2(3H)-furanone

<3S-<3α,5β(R^*)>>-5-(2-Cyclohexyl-1-azidoethyl)dihydro-3-isopropyl-2(3H)-furanone

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