4-Methoxy-3-((R)-2-{(1R,2R,6S)-2-[(E)-2-((2S,3S,6R)-6-{(E)-3-[(2S,5S)-5-((R)-1-methoxy-ethyl)-tetrahydro-furan-2-yl]-propenyl}-3-methyl-tetrahydro-pyran-2-yl)-3-triethylsilanyloxy-propenyl]-6-methyl-cyclohexyl}-propionyl)-5-methylene-5H-furan-2-one

Base Information

• Chemical Name: 4-Methoxy-3-((R)-2-{(1R,2R,6S)-2-[(E)-2-((2S,3S,6R)-6-{(E)-3-[(2S,5S)-5-((R)-1-methoxy-ethyl)-tetrahydro-furan-2-yl]-propenyl}-3-methyl-tetrahydro-pyran-2-yl)-3-triethylsilanyloxy-propenyl]-6-methyl-cyclohexyl}-propionyl)-5-methylene-5H-furan-2-one
• CAS No.: 142459-48-1
• Molecular Formula: C₄₁H₆₆O₈Si
• Molecular Weight: 715.056
• Mol file: 142459-48-1.mol

Synonyms:4-Methoxy-3-((R)-2-{(1R,2R,6S)-2-[(E)-2-((2S,3S,6R)-6-{(E)-3-[(2S,5S)-5-((R)-1-methoxy-ethyl)-tetrahydro-furan-2-yl]-propenyl}-3-methyl-tetrahydro-pyran-2-yl)-3-triethylsilanyloxy-propenyl]-6-methyl-cyclohexyl}-propionyl)-5-methylene-5H-furan-2-one

Chemical Property of 4-Methoxy-3-((R)-2-{(1R,2R,6S)-2-[(E)-2-((2S,3S,6R)-6-{(E)-3-[(2S,5S)-5-((R)-1-methoxy-ethyl)-tetrahydro-furan-2-yl]-propenyl}-3-methyl-tetrahydro-pyran-2-yl)-3-triethylsilanyloxy-propenyl]-6-methyl-cyclohexyl}-propionyl)-5-methylene-5H-furan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Methoxy-3-((R)-2-{(1R,2R,6S)-2-[(E)-2-((2S,3S,6R)-6-{(E)-3-[(2S,5S)-5-((R)-1-methoxy-ethyl)-tetrahydro-furan-2-yl]-propenyl}-3-methyl-tetrahydro-pyran-2-yl)-3-triethylsilanyloxy-propenyl]-6-methyl-cyclohexyl}-propionyl)-5-methylene-5H-furan-2-one

There total 62 articles about 4-Methoxy-3-((R)-2-{(1R,2R,6S)-2-[(E)-2-((2S,3S,6R)-6-{(E)-3-[(2S,5S)-5-((R)-1-methoxy-ethyl)-tetrahydro-furan-2-yl]-propenyl}-3-methyl-tetrahydro-pyran-2-yl)-3-triethylsilanyloxy-propenyl]-6-methyl-cyclohexyl}-propionyl)-5-methylene-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:

(E)-(4R,5S)-4-Acetoxy-5-(methanesulfonyloxy)-2-hexenal (142459-13-0) → 4-Methoxy-3-((R)-2-{(1R,2R,6S)-2-[(E)-2-((2S,3S,6R)-6-{(E)-3-[(2S,5S)-5-((R)-1-methoxy-ethyl)-tetrahydro-furan-2-yl]-propenyl}-3-methyl-tetrahydro-pyran-2-yl)-3-triethylsilanyloxy-propenyl]-6-methyl-cyclohexyl}-propionyl)-5-methylene-5H-furan-2-one (142459-48-1)

Guidance literature:

Multi-step reaction with 18 steps

1: 98 percent / H₂ / 10percent Pd/C / ethyl acetate / 4 h

2: methanol / 9.5 h / 5 °C

3: imidazole / dimethylformamide / 1 h / Ambient temperature

4: 93 percent / BF₃*OEt₂ / CH₂Cl₂ / 1 h / 0 °C

5: 83 percent / Bu₄NF / tetrahydrofuran

6: 1) NaH / 1) THF 2) r.t., 1 h

7: 99 percent / DIBALH / hexane; diethyl ether / 0.08 h

8: 1) oxalyl chloride, DMSO, 2) Et₃N / 1) CH₂Cl₂, -80 deg C - 60 deg C, 1 h, 2) - 40 deg C, 30 min

9: NaClO₂, 2-methyl-2-butene, NaH₂PO₄*2H₂O / 2-methyl-propan-2-ol / 0.33 h / Ambient temperature

10: 142 mg / diethyl ether

11: 1.23 g / LDA / tetrahydrofuran; hexane / 0.58 h / -100 °C

12: 1.17 g / DMAP, pyridine / 48 h / Ambient temperature

13: 1,8-diazabicyclo<5.4.0>undec-7-ene / 48 h / Ambient temperature

14: acetone / Irradiation

15: 50 mg / DIBALH / toluene; hexane / 0.58 h / -80 - -70 °C

16: 44 mg / imidazole, Et₃N / CH₂Cl₂ / 0.58 h / Ambient temperature

17: 1) LDA, 2) N,N'-dimethylpropyleneurea / 1) THF, hexane, 2) THF, -100 deg C - -95 deg C, 20 min

18: 18.1 mg / PCC, molecular sieves (4-Angstroem) / CH₂Cl₂ / 0.33 h

With pyridine; 1H-imidazole; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;

DOI:10.1021/jo00036a026

Reference yield:

(4S,5S)-5-<<(tert-Butyldimethylsilyl)oxy>-methyl>-4-<(1R)-1-cyanoethyl>-3-methylcyclohex-2-en-1-one (142560-63-2) → 4-Methoxy-3-((R)-2-{(1R,2R,6S)-2-[(E)-2-((2S,3S,6R)-6-{(E)-3-[(2S,5S)-5-((R)-1-methoxy-ethyl)-tetrahydro-furan-2-yl]-propenyl}-3-methyl-tetrahydro-pyran-2-yl)-3-triethylsilanyloxy-propenyl]-6-methyl-cyclohexyl}-propionyl)-5-methylene-5H-furan-2-one (142459-48-1)

Guidance literature:

Multi-step reaction with 13 steps

1: 72 percent / H₂ / 10percent Pd/C / ethanol

2: ethanol / 1.5 h / Heating

3: 627 mg / catecholborane, NaOAc*3H₂O / CHCl₃; tetrahydrofuran / 48 h / Heating

4: 473 mg / 5percent HF / acetonitrile / 0.75 h / 0 °C

5: 1) oxalyl chloride, DMSO, 2) Et₃N / 1) CH₂Cl₂, -80 deg C - -60 deg C, 1 h, 2) -60 deg C, 50 min

6: 1.23 g / LDA / tetrahydrofuran; hexane / 0.58 h / -100 °C

7: 1.17 g / DMAP, pyridine / 48 h / Ambient temperature

8: 1,8-diazabicyclo<5.4.0>undec-7-ene / 48 h / Ambient temperature

9: acetone / Irradiation

10: 50 mg / DIBALH / toluene; hexane / 0.58 h / -80 - -70 °C

11: 44 mg / imidazole, Et₃N / CH₂Cl₂ / 0.58 h / Ambient temperature

12: 1) LDA, 2) N,N'-dimethylpropyleneurea / 1) THF, hexane, 2) THF, -100 deg C - -95 deg C, 20 min

13: 18.1 mg / PCC, molecular sieves (4-Angstroem) / CH₂Cl₂ / 0.33 h

With pyridine; 1H-imidazole; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; oxalyl dichloride; 4 A molecular sieve; hydrogen fluoride; hydrogen; sodium acetate; diisobutylaluminium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide; benzo[1,3,2]dioxaborole; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; chloroform; acetone; toluene; acetonitrile;

DOI:10.1021/jo00036a026

Reference yield:

3-<<(tert-Butyldimethylsilyl)oxy>methyl>-1-methoxy-5-methyl-1,4-cyclohexadiene (124908-72-1) → 4-Methoxy-3-((R)-2-{(1R,2R,6S)-2-[(E)-2-((2S,3S,6R)-6-{(E)-3-[(2S,5S)-5-((R)-1-methoxy-ethyl)-tetrahydro-furan-2-yl]-propenyl}-3-methyl-tetrahydro-pyran-2-yl)-3-triethylsilanyloxy-propenyl]-6-methyl-cyclohexyl}-propionyl)-5-methylene-5H-furan-2-one (142459-48-1)

Guidance literature:

Multi-step reaction with 19 steps

1: 1) 2,6-di-tert-butylcresol, dichloromaleic anhydride 2) NaOMe / 1) chlorobenzene, 150 deg C, 24 h 2) MeOH, 0 deg C, 50 min

2: HF / acetonitrile / 1 h / 0 °C / Resolution: 1) isooctane, benzene, (Ac)2O, Amano lipase CES on Celite, 23 deg C, 5 h, 2) chromatography (silica gel, AcOEt/hexane), 3) recrystallization (Et₂O)

3: 99 percent / imidazole / CH₂Cl₂ / 1 h / Ambient temperature

4: 69 percent / 1) lithium hexamethyldisilazane, 2) HMPA / 1) THF, hexane, -50 deg C - -60 deg C, 1 h, 2) -35 deg C, 24 h

5: 98 percent / NH₂OH*HCl, pyridine / CH₂Cl₂ / 15 h / Heating

6: 1) TsCl, DMAP, pyridine, 2) LiCl, MeOH / 1) CH₂Cl₂, -80 deg C - r.t., 1 h, 2) r.t., 2 weeks

7: 72 percent / H₂ / 10percent Pd/C / ethanol

8: ethanol / 1.5 h / Heating

9: 627 mg / catecholborane, NaOAc*3H₂O / CHCl₃; tetrahydrofuran / 48 h / Heating

10: 473 mg / 5percent HF / acetonitrile / 0.75 h / 0 °C

11: 1) oxalyl chloride, DMSO, 2) Et₃N / 1) CH₂Cl₂, -80 deg C - -60 deg C, 1 h, 2) -60 deg C, 50 min

12: 1.23 g / LDA / tetrahydrofuran; hexane / 0.58 h / -100 °C

13: 1.17 g / DMAP, pyridine / 48 h / Ambient temperature

14: 1,8-diazabicyclo<5.4.0>undec-7-ene / 48 h / Ambient temperature

15: acetone / Irradiation

16: 50 mg / DIBALH / toluene; hexane / 0.58 h / -80 - -70 °C

17: 44 mg / imidazole, Et₃N / CH₂Cl₂ / 0.58 h / Ambient temperature

18: 1) LDA, 2) N,N'-dimethylpropyleneurea / 1) THF, hexane, 2) THF, -100 deg C - -95 deg C, 20 min

19: 18.1 mg / PCC, molecular sieves (4-Angstroem) / CH₂Cl₂ / 0.33 h

With pyridine; 1H-imidazole; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; dichloromaleic acid anhydride; oxalyl dichloride; 4 A molecular sieve; 2,4-di-t-butyl-3-methyl phenol; hydrogen fluoride; hydroxylamine hydrochloride; hydrogen; sodium methylate; sodium acetate; diisobutylaluminium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; p-toluenesulfonyl chloride; pyridinium chlorochromate; lithium chloride; lithium hexamethyldisilazane; lithium diisopropyl amide; benzo[1,3,2]dioxaborole; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; chloroform; acetone; toluene; acetonitrile;

DOI:10.1021/jo00036a026

upstream raw materials:

C₄₁H₆₈O₈Si

(R)-1-((S)-5-Methoxy-tetrahydro-furan-2-yl)-ethanol

(R)-6-Hydroxymethyl-3-methyl-tetrahydro-pyran-2-one

(R)-4-(2,2-dimethyl-1,3-dioxolan-4-yl)butyric acid

Downstream raw materials:

3-((R)-2-{(1R,2R,6S)-2-[(E)-3-Hydroxy-2-((2S,3S,6R)-6-{(E)-3-[(2S,5S)-5-((R)-1-methoxy-ethyl)-tetrahydro-furan-2-yl]-propenyl}-3-methyl-tetrahydro-pyran-2-yl)-propenyl]-6-methyl-cyclohexyl}-propionyl)-4-methoxy-5-methylene-5H-furan-2-one