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

Base Information

• Chemical Name: 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
• CAS No.: 179815-41-9
• Molecular Formula: C₃₄H₄₉IO₃Si
• Molecular Weight: 660.751

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 20 articles about 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 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:

2(R)-(3-methyl-4-hydroxy-2(E)-butenyl)-4(S)-<(tert-butyldiphenylsilyl)oxy>-8(R)-isopropyl-9(S)-methyl-1,7-dioxaspiro<5.5>undecane (114066-22-7) → 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 (179815-41-9)

Guidance literature:

With methyltriphenoxyphosphonium iodide; In N,N-dimethyl-formamide; at 25 ℃; for 0.333333h;

DOI:10.1021/ja961071u

Reference yield:

(E)-4-methyl-pent-2-en-1-ol (69143-05-1) → 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 (179815-41-9)

Guidance literature:

Multi-step reaction with 18 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

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; 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) → 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 (179815-41-9)

Guidance literature:

Multi-step reaction with 19 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

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; 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

upstream raw materials:

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

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

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

(2R,3R)-(3-isopropyloxiran-2-yl)methanol

Downstream raw materials:

(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

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

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