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

Base Information

• Chemical Name: <3R-<3α,5α(S^*)>>-5-(2-Cyclohexyl-1-hydroxyethyl)dihydro-3-isopropyl-2(3H)-furanone
• CAS No.: 134922-55-7
• Molecular Formula: C₁₅H₂₆O₃
• Molecular Weight: 254.37

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

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

There total 13 articles about <3R-<3α,5α(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: 94.0%

<3R-(3α,5β,6α)>-5-<(tert-Butyldimethylsilyl)oxy>tetrahydro-6-(cyclohexylmethyl)-3-isopropyl-2H-pyran-2-one (125816-12-8) → <3R-<3α,5α(S*)>>-5-(2-Cyclohexyl-1-hydroxyethyl)dihydro-3-isopropyl-2(3H)-furanone (134922-55-7)

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-enopyranoside (134934-18-2) → <3R-<3α,5α(S*)>>-5-(2-Cyclohexyl-1-hydroxyethyl)dihydro-3-isopropyl-2(3H)-furanone (134922-55-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 57 percent / 1,3-dicyclohexylcarbodiimide, dimethyl sulfoxide, H₃PO₄ / 16 h / Ambient temperature

2: 1.) lithium bis(trimethylsilyl)amide / 1.) THF, reflux, 45 min, 2.) r.t., 1.5 h

3: 57 percent / Jones reagent, MgSO₄ / acetone / 0.17 h / 0 - 5 °C

4: 86 percent / hydrogen / 5 percent Pd/C / ethyl acetate / 1 h / Ambient temperature

5: 1.) lithium bis(trimethylsilyl)amide / 1.) THF, -78 deg C, 10 min, 2.) -78 deg C, 15 min

6: 3.28 g / pyridine / 1 h / Ambient temperature

7: 1,5-diazabicyclo<4.3.0>non-5-ene / tetrahydrofuran / 0.17 h / Ambient temperature

8: 1.) CuI / 1.) Et₂O, 0 deg C, 2.) 0-5 deg C, 15 min

9: 94 percent / 4 N aq. HCl / methanol / 0.33 h / Heating

With pyridine; hydrogenchloride; copper(l) iodide; jones reagent; phosphoric acid; DBN; hydrogen; magnesium sulfate; dimethyl sulfoxide; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; ethyl acetate; acetone;

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) → <3R-<3α,5α(S*)>>-5-(2-Cyclohexyl-1-hydroxyethyl)dihydro-3-isopropyl-2(3H)-furanone (134922-55-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) lithium bis(trimethylsilyl)amide / 1.) THF, reflux, 45 min, 2.) r.t., 1.5 h

2: 57 percent / Jones reagent, MgSO₄ / acetone / 0.17 h / 0 - 5 °C

3: 86 percent / hydrogen / 5 percent Pd/C / ethyl acetate / 1 h / Ambient temperature

4: 1.) lithium bis(trimethylsilyl)amide / 1.) THF, -78 deg C, 10 min, 2.) -78 deg C, 15 min

5: 3.28 g / pyridine / 1 h / Ambient temperature

6: 1,5-diazabicyclo<4.3.0>non-5-ene / tetrahydrofuran / 0.17 h / Ambient temperature

7: 1.) CuI / 1.) Et₂O, 0 deg C, 2.) 0-5 deg C, 15 min

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

With pyridine; hydrogenchloride; copper(l) iodide; jones reagent; DBN; hydrogen; magnesium sulfate; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; ethyl acetate; acetone;

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

upstream raw materials:

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

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

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:

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

<3R-<3α,5α(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

<2R,4S,5S>-6-Cyclohexyl-5-<(N-cyclohexyl-N-methyl)glycyl-3-(1-naphthyl)-L-alanyl-3-(4-thiazolyl)-L-alanyl)amino>-4-hydroxy-2-isopropylhexanoyl-<2-(4-morpholino)ethyl>amide

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

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