(S)-3-{(E)-(S)-6-[(2R,4S,6R,8R,9S)-4-(tert-Butyl-diphenyl-silanyloxy)-8-isopropyl-9-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-2,4-dimethyl-hex-4-enoyl}-4-isopropyl-oxazolidin-2-one

Base Information

• Chemical Name: (S)-3-{(E)-(S)-6-[(2R,4S,6R,8R,9S)-4-(tert-Butyl-diphenyl-silanyloxy)-8-isopropyl-9-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-2,4-dimethyl-hex-4-enoyl}-4-isopropyl-oxazolidin-2-one
• CAS No.: 179815-42-0
• Molecular Formula: C₄₃H₆₃NO₆Si
• Molecular Weight: 718.062

Synonyms:(S)-3-{(E)-(S)-6-[(2R,4S,6R,8R,9S)-4-(tert-Butyl-diphenyl-silanyloxy)-8-isopropyl-9-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-2,4-dimethyl-hex-4-enoyl}-4-isopropyl-oxazolidin-2-one

Chemical Property of (S)-3-{(E)-(S)-6-[(2R,4S,6R,8R,9S)-4-(tert-Butyl-diphenyl-silanyloxy)-8-isopropyl-9-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-2,4-dimethyl-hex-4-enoyl}-4-isopropyl-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-{(E)-(S)-6-[(2R,4S,6R,8R,9S)-4-(tert-Butyl-diphenyl-silanyloxy)-8-isopropyl-9-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-2,4-dimethyl-hex-4-enoyl}-4-isopropyl-oxazolidin-2-one

There total 21 articles about (S)-3-{(E)-(S)-6-[(2R,4S,6R,8R,9S)-4-(tert-Butyl-diphenyl-silanyloxy)-8-isopropyl-9-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-2,4-dimethyl-hex-4-enoyl}-4-isopropyl-oxazolidin-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)-4-methyl-pent-2-en-1-ol (69143-05-1) → (S)-3-{(E)-(S)-6-[(2R,4S,6R,8R,9S)-4-(tert-Butyl-diphenyl-silanyloxy)-8-isopropyl-9-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-2,4-dimethyl-hex-4-enoyl}-4-isopropyl-oxazolidin-2-one (179815-42-0)

Guidance literature:

Multi-step reaction with 19 steps

1: 74 percent / (-)-diethyl tartrate, Ti(i-Pr)4, t-BuOOH / CH₂Cl₂ / 20 h / -20 °C

2: 2.) NaIO₄ / 1.) Et₂O, 0 deg C, 3.5 h, 2.) H₂O, 16 h

3: 82 percent / pyridine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h / 0 - 20 °C

4: 92 percent / Et₃N, 4-(dimethylamino)pyridine / 8 h / Ambient temperature

5: 88 percent / NaI / butan-2-one / 4 h / Heating

6: 94 percent / LDA, hexamethylphosphoramide / tetrahydrofuran / 0.08 h

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

8: 88 percent / K₂CO₃ / 16 h / Ambient temperature

9: TsOH / tetrahydrofuran; H₂O

10: 78 percent / <(n-Bu₃P)3CuI>4 / tetrahydrofuran / 0.5 h / -45 °C

11: 25 percent / NaBH₄ / 1,2-dimethoxy-ethane / 1 h

12: 1.) CrO₃, H₂SO₄, 2.) NaBH₄ / 1.) acetone, 10 min, 2.) DME, 1 h

13: 100 percent / imidazole, 4-(dimethylamino)pyridine / dimethylformamide / 60 h / 25 °C

14: 1.) 9-BBN, 2.) aq. H₂O₂, aq. NaOH / 1.) THF, irradiation, 1 h, 2.) THF, 3 h

15: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, -60 deg C, 5 min

16: 89 percent / CH₂Cl₂ / 16 h / Heating

17: 91 percent / i-Bu₂AlH / tetrahydrofuran / 0.67 h / -78 °C

18: methyltriphenoxyphosphonium iodide / dimethylformamide / 0.33 h / 25 °C

19: 1.) sodium hexamethyldisilazide / 1.) THF, -78 deg C, 1 h, 2.) THF, -78 deg C, 3 h

With pyridine; 1H-imidazole; chromium(VI) oxide; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium hydroxide; sodium tetrahydroborate; sodium periodate; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; oxalyl dichloride; <(n-Bu3P)3CuI>4; sulfuric acid; methyltriphenoxyphosphonium iodide; dihydrogen peroxide; sodium hexamethyldisilazane; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; isopropyl titanoate(IV); dimethyl sulfoxide; (-)-diethyl tartrate; triethylamine; sodium iodide; lithium diisopropyl amide; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide; butanone;

DOI:10.1021/ja961071u

Reference yield:

ethyl-4-methyl-2-(E)-penteneoate (15790-86-0) → (S)-3-{(E)-(S)-6-[(2R,4S,6R,8R,9S)-4-(tert-Butyl-diphenyl-silanyloxy)-8-isopropyl-9-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-2,4-dimethyl-hex-4-enoyl}-4-isopropyl-oxazolidin-2-one (179815-42-0)

Guidance literature:

Multi-step reaction with 20 steps

1: 97 percent / iBu₂AlH / tetrahydrofuran / -78 - 0 °C

2: 74 percent / (-)-diethyl tartrate, Ti(i-Pr)4, t-BuOOH / CH₂Cl₂ / 20 h / -20 °C

3: 2.) NaIO₄ / 1.) Et₂O, 0 deg C, 3.5 h, 2.) H₂O, 16 h

4: 82 percent / pyridine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h / 0 - 20 °C

5: 92 percent / Et₃N, 4-(dimethylamino)pyridine / 8 h / Ambient temperature

6: 88 percent / NaI / butan-2-one / 4 h / Heating

7: 94 percent / LDA, hexamethylphosphoramide / tetrahydrofuran / 0.08 h

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

9: 88 percent / K₂CO₃ / 16 h / Ambient temperature

10: TsOH / tetrahydrofuran; H₂O

11: 78 percent / <(n-Bu₃P)3CuI>4 / tetrahydrofuran / 0.5 h / -45 °C

12: 25 percent / NaBH₄ / 1,2-dimethoxy-ethane / 1 h

13: 1.) CrO₃, H₂SO₄, 2.) NaBH₄ / 1.) acetone, 10 min, 2.) DME, 1 h

14: 100 percent / imidazole, 4-(dimethylamino)pyridine / dimethylformamide / 60 h / 25 °C

15: 1.) 9-BBN, 2.) aq. H₂O₂, aq. NaOH / 1.) THF, irradiation, 1 h, 2.) THF, 3 h

16: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, -60 deg C, 5 min

17: 89 percent / CH₂Cl₂ / 16 h / Heating

18: 91 percent / i-Bu₂AlH / tetrahydrofuran / 0.67 h / -78 °C

19: methyltriphenoxyphosphonium iodide / dimethylformamide / 0.33 h / 25 °C

20: 1.) sodium hexamethyldisilazide / 1.) THF, -78 deg C, 1 h, 2.) THF, -78 deg C, 3 h

With pyridine; 1H-imidazole; chromium(VI) oxide; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium hydroxide; sodium tetrahydroborate; sodium periodate; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; oxalyl dichloride; <(n-Bu3P)3CuI>4; sulfuric acid; methyltriphenoxyphosphonium iodide; dihydrogen peroxide; sodium hexamethyldisilazane; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; isopropyl titanoate(IV); dimethyl sulfoxide; (-)-diethyl tartrate; triethylamine; sodium iodide; lithium diisopropyl amide; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide; butanone;

DOI:10.1021/ja961071u

Reference yield:

(2R,3R)-(3-isopropyloxiran-2-yl)methanol (97906-31-5) → (S)-3-{(E)-(S)-6-[(2R,4S,6R,8R,9S)-4-(tert-Butyl-diphenyl-silanyloxy)-8-isopropyl-9-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-2,4-dimethyl-hex-4-enoyl}-4-isopropyl-oxazolidin-2-one (179815-42-0)

Guidance literature:

Multi-step reaction with 18 steps

1: 2.) NaIO₄ / 1.) Et₂O, 0 deg C, 3.5 h, 2.) H₂O, 16 h

2: 82 percent / pyridine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 24 h / 0 - 20 °C

3: 92 percent / Et₃N, 4-(dimethylamino)pyridine / 8 h / Ambient temperature

4: 88 percent / NaI / butan-2-one / 4 h / Heating

5: 94 percent / LDA, hexamethylphosphoramide / tetrahydrofuran / 0.08 h

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

7: 88 percent / K₂CO₃ / 16 h / Ambient temperature

8: TsOH / tetrahydrofuran; H₂O

9: 78 percent / <(n-Bu₃P)3CuI>4 / tetrahydrofuran / 0.5 h / -45 °C

10: 25 percent / NaBH₄ / 1,2-dimethoxy-ethane / 1 h

11: 1.) CrO₃, H₂SO₄, 2.) NaBH₄ / 1.) acetone, 10 min, 2.) DME, 1 h

12: 100 percent / imidazole, 4-(dimethylamino)pyridine / dimethylformamide / 60 h / 25 °C

13: 1.) 9-BBN, 2.) aq. H₂O₂, aq. NaOH / 1.) THF, irradiation, 1 h, 2.) THF, 3 h

14: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) CH₂Cl₂, -60 deg C, 5 min

15: 89 percent / CH₂Cl₂ / 16 h / Heating

16: 91 percent / i-Bu₂AlH / tetrahydrofuran / 0.67 h / -78 °C

17: methyltriphenoxyphosphonium iodide / dimethylformamide / 0.33 h / 25 °C

18: 1.) sodium hexamethyldisilazide / 1.) THF, -78 deg C, 1 h, 2.) THF, -78 deg C, 3 h

With pyridine; 1H-imidazole; chromium(VI) oxide; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium hydroxide; sodium tetrahydroborate; sodium periodate; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; oxalyl dichloride; <(n-Bu3P)3CuI>4; sulfuric acid; methyltriphenoxyphosphonium iodide; dihydrogen peroxide; sodium hexamethyldisilazane; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; sodium iodide; lithium diisopropyl amide; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide; butanone;

DOI:10.1021/ja961071u

upstream raw materials:

N-isopropyl oxazolidinone

tert-Butyl-[(2R,4S,6R,8R,9S)-2-((E)-4-iodo-3-methyl-but-2-enyl)-8-isopropyl-9-methyl-1,7-dioxa-spiro[5.5]undec-4-yloxy]-diphenyl-silane

(E)-4-methyl-pent-2-en-1-ol

ethyl-4-methyl-2-(E)-penteneoate

Downstream raw materials:

2(R)-<3,5(R)-dimethyl-6-hydroxy-2(E)-hexenyl>-4(S)-<(tert-butyldiphenylsilyl)oxy>-8(R)-isopropyl-9(S)-methyl-1,7-dioxaspiro<5.5>undecane

C₃₉H₅₂O₆S

C₃₉H₅₂O₇S

C₅₅H₇₄O₆SSi

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