(4S)-4-<(1S,2R)-5-(tert-butyldiphenylsiloxy)-1-<(1S)-1-hydroxy-2-(phenylselenyl)ethyl>-2-methylpentyl>dihydro-2(3H)-furanone

Base Information

• Chemical Name: (4S)-4-<(1S,2R)-5-(tert-butyldiphenylsiloxy)-1-<(1S)-1-hydroxy-2-(phenylselenyl)ethyl>-2-methylpentyl>dihydro-2(3H)-furanone
• CAS No.: 173864-64-7
• Molecular Formula: C₃₄H₄₄O₄SeSi
• Molecular Weight: 623.766

Synonyms:(4S)-4-<(1S,2R)-5-(tert-butyldiphenylsiloxy)-1-<(1S)-1-hydroxy-2-(phenylselenyl)ethyl>-2-methylpentyl>dihydro-2(3H)-furanone

Chemical Property of (4S)-4-<(1S,2R)-5-(tert-butyldiphenylsiloxy)-1-<(1S)-1-hydroxy-2-(phenylselenyl)ethyl>-2-methylpentyl>dihydro-2(3H)-furanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (4S)-4-<(1S,2R)-5-(tert-butyldiphenylsiloxy)-1-<(1S)-1-hydroxy-2-(phenylselenyl)ethyl>-2-methylpentyl>dihydro-2(3H)-furanone

There total 22 articles about (4S)-4-<(1S,2R)-5-(tert-butyldiphenylsiloxy)-1-<(1S)-1-hydroxy-2-(phenylselenyl)ethyl>-2-methylpentyl>dihydro-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:

(3R)-citronellol (1117-61-9) → (4S)-4-<(1S,2R)-5-(tert-butyldiphenylsiloxy)-1-<(1S)-1-hydroxy-2-(phenylselenyl)ethyl>-2-methylpentyl>dihydro-2(3H)-furanone (173864-64-7)

Guidance literature:

Multi-step reaction with 20 steps

1: 100 percent / pyridine, DMAP / CH₂Cl₂ / 0.75 h / 0 °C

2: 1.) O₃, 2.) BH₃*SMe₂ / 1.) CH₂Cl₂, -78 deg C, 2 h, 2.) CH₂Cl₂, 0 deg C, 3 h

3: 100 percent / DMAP, Et₃N / CH₂Cl₂ / Ambient temperature

4: 100 percent / aq. K₂CO₃ / methanol / 4 h / Heating

5: 17.5 g / pyridinium dichromate, 4A molecular sieves / CH₂Cl₂ / 1 h / Ambient temperature

6: NaClO₂, NaH₂PO₄*H₂O / 2-methyl-propan-2-ol; various solvent(s) / 6 h / Ambient temperature

7: 82 percent / diethyl ether / 1 h / Ambient temperature

8: 1.) LDA / 1.) THF, -78 deg C, 1 h, 2.) THF, -78 deg C, 30 min

9: 89 percent / diisopropylethylamine / CH₂Cl₂ / 12 h / Ambient temperature

10: 60 percent / 10percent aq. H₂SO₄ / tetrahydrofuran / 24 h

11: 44 percent / DBU / benzene / 9 h / 70 °C

12: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 3 min, 2.) THF, hexane, -78 deg C, 30 min

13: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, CH₃OH, -78 deg C, 2.) CH₂Cl₂, CH₃OH, from -78 deg C to RT, 1.5 h

14: 90 percent / p-TsOH*H₂O / methanol / 0.17 h

15: 97 percent / Dibal-H / CH₂Cl₂; hexane / 0.42 h / -78 °C

16: 1.) KN(SiMe₃)2 / 1.) THF, toluene, 30 min, 2.) THF, toluene, RT, 4.5 h

17: 78 percent / 5percent aq. HCl / tetrahydrofuran / 7 h

18: 97 percent / pyridinium dichromate, 4a molecular sieves / CH₂Cl₂ / 6 h / Ambient temperature

19: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, RT, 5 h

20: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 40 min, 2.) THF, hexane, -78 deg C, 40 min

With pyridine; hydrogenchloride; dmap; sodium chlorite; sodium dihydrogenphosphate; dipyridinium dichromate; n-butyllithium; dimethylsulfide; dimethylsulfide borane complex; 4 A molecular sieve; sulfuric acid; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; tert-butyl alcohol; benzene;

DOI:10.1021/ja9533609

Reference yield:

(R)-1-citronellyl acetate (20425-54-1,67650-82-2) → (4S)-4-<(1S,2R)-5-(tert-butyldiphenylsiloxy)-1-<(1S)-1-hydroxy-2-(phenylselenyl)ethyl>-2-methylpentyl>dihydro-2(3H)-furanone (173864-64-7)

Guidance literature:

Multi-step reaction with 19 steps

1: 1.) O₃, 2.) BH₃*SMe₂ / 1.) CH₂Cl₂, -78 deg C, 2 h, 2.) CH₂Cl₂, 0 deg C, 3 h

2: 100 percent / DMAP, Et₃N / CH₂Cl₂ / Ambient temperature

3: 100 percent / aq. K₂CO₃ / methanol / 4 h / Heating

4: 17.5 g / pyridinium dichromate, 4A molecular sieves / CH₂Cl₂ / 1 h / Ambient temperature

5: NaClO₂, NaH₂PO₄*H₂O / 2-methyl-propan-2-ol; various solvent(s) / 6 h / Ambient temperature

6: 82 percent / diethyl ether / 1 h / Ambient temperature

7: 1.) LDA / 1.) THF, -78 deg C, 1 h, 2.) THF, -78 deg C, 30 min

8: 89 percent / diisopropylethylamine / CH₂Cl₂ / 12 h / Ambient temperature

9: 60 percent / 10percent aq. H₂SO₄ / tetrahydrofuran / 24 h

10: 44 percent / DBU / benzene / 9 h / 70 °C

11: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 3 min, 2.) THF, hexane, -78 deg C, 30 min

12: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, CH₃OH, -78 deg C, 2.) CH₂Cl₂, CH₃OH, from -78 deg C to RT, 1.5 h

13: 90 percent / p-TsOH*H₂O / methanol / 0.17 h

14: 97 percent / Dibal-H / CH₂Cl₂; hexane / 0.42 h / -78 °C

15: 1.) KN(SiMe₃)2 / 1.) THF, toluene, 30 min, 2.) THF, toluene, RT, 4.5 h

16: 78 percent / 5percent aq. HCl / tetrahydrofuran / 7 h

17: 97 percent / pyridinium dichromate, 4a molecular sieves / CH₂Cl₂ / 6 h / Ambient temperature

18: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, RT, 5 h

19: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 40 min, 2.) THF, hexane, -78 deg C, 40 min

With hydrogenchloride; dmap; sodium chlorite; sodium dihydrogenphosphate; dipyridinium dichromate; n-butyllithium; dimethylsulfide; dimethylsulfide borane complex; 4 A molecular sieve; sulfuric acid; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; tert-butyl alcohol; benzene;

DOI:10.1021/ja9533609

Reference yield:

(R)-(+)-6-Hydroxy-3-methylhexyl acetate (82425-91-0) → (4S)-4-<(1S,2R)-5-(tert-butyldiphenylsiloxy)-1-<(1S)-1-hydroxy-2-(phenylselenyl)ethyl>-2-methylpentyl>dihydro-2(3H)-furanone (173864-64-7)

Guidance literature:

Multi-step reaction with 18 steps

1: 100 percent / DMAP, Et₃N / CH₂Cl₂ / Ambient temperature

2: 100 percent / aq. K₂CO₃ / methanol / 4 h / Heating

3: 17.5 g / pyridinium dichromate, 4A molecular sieves / CH₂Cl₂ / 1 h / Ambient temperature

4: NaClO₂, NaH₂PO₄*H₂O / 2-methyl-propan-2-ol; various solvent(s) / 6 h / Ambient temperature

5: 82 percent / diethyl ether / 1 h / Ambient temperature

6: 1.) LDA / 1.) THF, -78 deg C, 1 h, 2.) THF, -78 deg C, 30 min

7: 89 percent / diisopropylethylamine / CH₂Cl₂ / 12 h / Ambient temperature

8: 60 percent / 10percent aq. H₂SO₄ / tetrahydrofuran / 24 h

9: 44 percent / DBU / benzene / 9 h / 70 °C

10: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 3 min, 2.) THF, hexane, -78 deg C, 30 min

11: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, CH₃OH, -78 deg C, 2.) CH₂Cl₂, CH₃OH, from -78 deg C to RT, 1.5 h

12: 90 percent / p-TsOH*H₂O / methanol / 0.17 h

13: 97 percent / Dibal-H / CH₂Cl₂; hexane / 0.42 h / -78 °C

14: 1.) KN(SiMe₃)2 / 1.) THF, toluene, 30 min, 2.) THF, toluene, RT, 4.5 h

15: 78 percent / 5percent aq. HCl / tetrahydrofuran / 7 h

16: 97 percent / pyridinium dichromate, 4a molecular sieves / CH₂Cl₂ / 6 h / Ambient temperature

17: 1.) O₃, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, RT, 5 h

18: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 40 min, 2.) THF, hexane, -78 deg C, 40 min

With hydrogenchloride; dmap; sodium chlorite; sodium dihydrogenphosphate; dipyridinium dichromate; n-butyllithium; dimethylsulfide; 4 A molecular sieve; sulfuric acid; potassium hexamethylsilazane; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; tert-butyl alcohol; benzene;

DOI:10.1021/ja9533609

upstream raw materials:

bis(phenylseleno)methane

(2S,3R)-6-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-2-((S)-5-oxo-tetrahydro-furan-3-yl)-hexanal

(3R)-citronellol

(R)-1-citronellyl acetate

Downstream raw materials:

(S)-4-{(1S,2R)-5-(tert-Butyl-diphenyl-silanyloxy)-1-[(S)-1-(1-methoxy-1-methyl-ethoxy)-2-phenylselanyl-ethyl]-2-methyl-pentyl}-dihydro-furan-2-one

(3aS,4R,6S,7S,7aR)-7-[(R)-4-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-butyl]-6-phenylselanylmethyl-4-((E)-propenyl)-hexahydro-furo[3,4-c]pyran-3-one

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