(S)-3-[(5E,7E)-(R)-9-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-4,4-dimethyl-nona-5,7-dienyl]-5-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-5H-furan-2-one

Base Information

• Chemical Name: (S)-3-[(5E,7E)-(R)-9-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-4,4-dimethyl-nona-5,7-dienyl]-5-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-5H-furan-2-one
• CAS No.: 248250-12-6
• Molecular Formula: C₄₁H₅₈O₅Si
• Molecular Weight: 658.994
• Mol file: 248250-12-6.mol

Synonyms:(S)-3-[(5E,7E)-(R)-9-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-4,4-dimethyl-nona-5,7-dienyl]-5-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-5H-furan-2-one

Chemical Property of (S)-3-[(5E,7E)-(R)-9-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-4,4-dimethyl-nona-5,7-dienyl]-5-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-5H-furan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-[(5E,7E)-(R)-9-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-4,4-dimethyl-nona-5,7-dienyl]-5-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-5H-furan-2-one

There total 7 articles about (S)-3-[(5E,7E)-(R)-9-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-4,4-dimethyl-nona-5,7-dienyl]-5-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-5H-furan-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: 88.0%

(5S)-(D-menthyloxy)-2(5H)-furanone (122079-41-8) + (5E,7E)-9-(tert-Butyl-diphenyl-silanyloxy)-4,4-dimethyl-nona-5,7-dienal (248250-11-5) → (S)-3-[(5E,7E)-(R)-9-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-4,4-dimethyl-nona-5,7-dienyl]-5-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-5H-furan-2-one (248250-12-6)

Guidance literature:

With lithium phenylselenide; In tetrahydrofuran; at -60 ℃; for 6h;

DOI:10.1055/s-2001-9711

Reference yield:

(2E,4E)-6,6-Dimethyl-nona-2,4,8-trienoic acid methyl ester (248250-07-9) → (S)-3-[(5E,7E)-(R)-9-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-4,4-dimethyl-nona-5,7-dienyl]-5-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-5H-furan-2-one (248250-12-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 98 percent / DIBALH / diethyl ether / 0.5 h / 0 °C

2.1: 100 percent / imidazole / dimethylformamide / 2 h / 20 °C

3.1: 9-BBN / tetrahydrofuran / 4 h / 20 °C

3.2: 91 percent / H₂O₂; NaOH / ethanol / 4 h / 0 °C

4.1: 98 percent / TEMPO; PhI(OAc)2 / 2 h / 20 °C

5.1: 88 percent / Li(SePh) / tetrahydrofuran / 6 h / -60 °C

With 1H-imidazole; 2,2,6,6-tetramethyl-piperidine-N-oxyl; 9-borabicyclo[3.3.1]nonane dimer; [bis(acetoxy)iodo]benzene; lithium phenylselenide; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1002/1099-0690(200102)2001:3<473::AID-EJOC473>3.0.CO;2-J

Reference yield:

tert-Butyl-((2E,4E)-6,6-dimethyl-nona-2,4,8-trienyloxy)-diphenyl-silane (248250-09-1) → (S)-3-[(5E,7E)-(R)-9-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-4,4-dimethyl-nona-5,7-dienyl]-5-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-5H-furan-2-one (248250-12-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 9-BBN / tetrahydrofuran / 4 h / 20 °C

1.2: 91 percent / H₂O₂; NaOH / ethanol / 4 h / 0 °C

2.1: 98 percent / TEMPO; PhI(OAc)2 / 2 h / 20 °C

3.1: 88 percent / Li(SePh) / tetrahydrofuran / 6 h / -60 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; 9-borabicyclo[3.3.1]nonane dimer; [bis(acetoxy)iodo]benzene; lithium phenylselenide; In tetrahydrofuran;

DOI:10.1002/1099-0690(200102)2001:3<473::AID-EJOC473>3.0.CO;2-J

upstream raw materials:

(5S)-(D-menthyloxy)-2(5H)-furanone

(5E,7E)-9-(tert-Butyl-diphenyl-silanyloxy)-4,4-dimethyl-nona-5,7-dienal

2,2-dimethyl-4-pentenal

(2E,4E)-6,6-dimethyl-2,4,8-nonatrien-1-ol

Downstream raw materials:

(3S,3aS,4S,6aS,10R,10aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-10-hydroxy-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-7,7-dimethyl-3,3a,4,6a,7,8,9,10-octahydro-2-oxa-cyclopenta[d]naphthalen-1-one

(3S,3aS,4S,6aS,10aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-7,7-dimethyl-3a,4,6a,7,8,9-hexahydro-3H-2-oxa-cyclopenta[d]naphthalene-1,10-dione

(3S,3aS,4S,6aS,10aR)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-7,7-dimethyl-3,3a,4,6a,7,8-hexahydro-2-oxa-cyclopenta[d]naphthalen-1-one

(3S,3aS,4S,6aS,10aR)-4-Hydroxymethyl-3-((1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyloxy)-7,7-dimethyl-3a,4,6a,7,8,9-hexahydro-3H-2-oxa-cyclopenta[d]naphthalene-1,10-dione