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

Base Information

• Chemical Name: <3S-<3α,5β(R^*)>>-5-(2-Cyclohexyl-1-azidoethyl)dihydro-3-isopropyl-2(3H)-furanone
• CAS No.: 118041-20-6
• Molecular Formula: C₁₅H₂₅N₃O₂
• Molecular Weight: 279.382

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

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

Chemical Property:

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

There total 35 articles about <3S-<3α,5β(R^*)>>-5-(2-Cyclohexyl-1-azidoethyl)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: 72.0%

5(R)-bromo-6-cyclohexyl-2(S)-isopropyl-4(S)-hexanolide (118041-14-8) → <3S-<3α,5β(R*)>>-5-(2-Cyclohexyl-1-azidoethyl)dihydro-3-isopropyl-2(3H)-furanone (118041-20-6) + 5-[2-Cyclohexyl-eth-(E)-ylidene]-3-isopropyl-dihydro-furan-2-one (118832-57-8) + (3S,5S)-5-((E)-2-Cyclohexyl-vinyl)-3-isopropyl-dihydro-furan-2-one (118832-56-7)

Guidance literature:

With sodium azide; In various solvent(s); for 72h; Yields of byproduct given; Ambient temperature;

DOI:10.1021/jo00266a034

Reference yield: 27.0%

(2S,4S,5R)-6-cyclohexyl-5-iodo-2-(1-methylethyl)-4-hexanolide (118832-51-2) → <3S-<3α,5β(R*)>>-5-(2-Cyclohexyl-1-azidoethyl)dihydro-3-isopropyl-2(3H)-furanone (118041-20-6) + 5-[2-Cyclohexyl-eth-(E)-ylidene]-3-isopropyl-dihydro-furan-2-one (118832-57-8) + (3S,5S)-5-((E)-2-Cyclohexyl-vinyl)-3-isopropyl-dihydro-furan-2-one (118832-56-7)

Guidance literature:

With sodium azide; In various solvent(s); for 72h; Yields of byproduct given; Ambient temperature;

DOI:10.1021/jo00266a034

Reference yield:

Ethyl 4-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enodialdopyranoside-(1,5) (112571-70-7) → <3S-<3α,5β(R*)>>-5-(2-Cyclohexyl-1-azidoethyl)dihydro-3-isopropyl-2(3H)-furanone (118041-20-6)

Guidance literature:

Multi-step reaction with 9 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

9: 1.) diethyl azodicarboxylate, PPh₃, 2.) (PhO)2P(O)N₃ / 1.) 5 min, 2.) THF, 25 deg C, 1.5 h

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

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

upstream raw materials:

5(R)-bromo-6-cyclohexyl-2(S)-isopropyl-4(S)-hexanolide

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

(2S,4S,5R)-6-cyclohexyl-5-iodo-2-(1-methylethyl)-4-hexanolide

diethyl isopropylmalonate

Downstream raw materials:

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

(2S,4S,5S)-5-amino-6-cyclohexyl-4-hydroxy-2-isopropyl hexanoic acid n-butyl amide

5(S)-azido-6-cyclohexyl-4(S)-hydroxy-2(S)-isopropylhexanoic acid n-butylamide

(2S,4S,5S)-5-benzyloxycarbonylamino-6-cyclohexyl-4-hydroxy-2-isopropyl hexanolide

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