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

Base Information

• Chemical Name: <3S-<3α,5β(S^*)>>-5-(2-Cyclohexyl-1-hydroxyethyl)dihydro-3-isopropyl-2(3H)-furanone
• CAS No.: 125816-09-3
• Molecular Formula: C₁₅H₂₆O₃
• Molecular Weight: 254.37

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 14 articles about <3S-<3α,5β(S^*)>>-5-(2-Cyclohexyl-1-hydroxyethyl)dihydro-3-isopropyl-2(3H)-furanone 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: 100.0%

<3S-(3α,5α,6β)>-5-<(tert-Butyldimethylsilyl)oxy>tetrahydro-6-(cyclohexylmethyl)-3-isopropyl-2H-pyran-2-one (125816-08-2) → <3S-<3α,5β(S*)>>-5-(2-Cyclohexyl-1-hydroxyethyl)dihydro-3-isopropyl-2(3H)-furanone (125816-09-3)

Guidance literature:

With hydrogenchloride; In methanol; for 0.333333h; Heating;

DOI:10.1016/S0040-4020(01)87085-X

Reference yield:

Ethyl 4-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enodialdopyranoside-(1,5) (112571-70-7) → <3S-<3α,5β(S*)>>-5-(2-Cyclohexyl-1-hydroxyethyl)dihydro-3-isopropyl-2(3H)-furanone (125816-09-3)

Guidance literature:

Multi-step reaction with 8 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

8: 94 percent / 4N HCl / methanol / 0.33 h / Heating

With chromium(VI) oxide; hydrogenchloride; 2,6-dichloro-benzonitrile; sulfuric acid; hydrogen; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; 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,5β(S*)>>-5-(2-Cyclohexyl-1-hydroxyethyl)dihydro-3-isopropyl-2(3H)-furanone (125816-09-3)

Guidance literature:

Multi-step reaction with 7 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

7: 94 percent / 4N HCl / methanol / 0.33 h / Heating

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

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

upstream raw materials:

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

cyclohexyltriphenylphosphorane

Ethyl 4-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enodialdopyranoside-(1,5)

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

Downstream raw materials:

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

<3S-<3α,5β(E)>>-5-(2-cyclohexylvinylene)dihydro-3-isopropyl-2(3H)-furanone

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

<3S-<3α,5β(R^*)>>-5-<2-Cyclohexyl-1-(N-cyclohexyl-N-methyl)glycyl-3-(1-naphthyl)-L-alanyl-3-(4-thiazolyl)-L-alanyl)aminoethyl>dihydro-3-isopropyl-2(3H)-furanone

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