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

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Chemical Name: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
CAS No.:114066-22-7
Molecular Formula:C₃₄H₅₀O₄Si
Molecular Weight:550.854
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 25 articles about 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 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: 91.0%

: 114066-21-6
2(R)-(3-methyl-4-ethoxy-4-oxo-2(E)-butenyl)-4(S)-<(tert-butyldiphenylsilyl)oxy>-8(R)-isopropyl-9(S)-methyl-1,7-dioxaspiro<5.5>undecane

: 114066-22-7
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

Guidance literature:: With diisobutylaluminium hydride; In tetrahydrofuran; at -78 ℃; for 3h;
DOI:10.1016/S0040-4039(00)96346-9

Reference yield:

: 114066-14-7
1-hydroxy-1(R)-isopropyl-9-methoxy-2(S)-methylnon-8-en-6-yn-5-one

: 114066-22-7
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

Guidance literature:: Multi-step reaction with 10 steps

1: 88 percent / K₂CO₃ / 16 h / Ambient temperature

2: TsOH / tetrahydrofuran; H₂O

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

4: 25 percent / NaBH₄ / 1,2-dimethoxy-ethane / 1 h

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

6: 100 percent / imidazole, 4-(dimethylamino)pyridine / dimethylformamide / 60 h / 25 °C

7: 1.) 9-BBN, 2.) aq. H₂O₂, aq. NaOH / 1.) THF, irradiation, 1 h, 2.) THF, 3 h

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

9: 89 percent / CH₂Cl₂ / 16 h / Heating

10: 91 percent / i-Bu₂AlH / tetrahydrofuran / 0.67 h / -78 °C

With 1H-imidazole; chromium(VI) oxide; dmap; sodium hydroxide; sodium tetrahydroborate; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; <(n-Bu3P)3CuI>4; sulfuric acid; dihydrogen peroxide; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ja961071u

Reference yield:

: 114066-15-8
1-hydroxy-1(R)-isopropyl-7,9,9-trimethoxy-2(S)-methylnon-6-en-5-one

: 114066-22-7
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

Guidance literature:: Multi-step reaction with 9 steps

1: TsOH / tetrahydrofuran; H₂O

2: 78 percent / <(n-Bu₃P)3CuI>4 / tetrahydrofuran / 0.5 h / -45 °C

3: 25 percent / NaBH₄ / 1,2-dimethoxy-ethane / 1 h

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

5: 100 percent / imidazole, 4-(dimethylamino)pyridine / dimethylformamide / 60 h / 25 °C

6: 1.) 9-BBN, 2.) aq. H₂O₂, aq. NaOH / 1.) THF, irradiation, 1 h, 2.) THF, 3 h

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

8: 89 percent / CH₂Cl₂ / 16 h / Heating

9: 91 percent / i-Bu₂AlH / tetrahydrofuran / 0.67 h / -78 °C

With 1H-imidazole; chromium(VI) oxide; dmap; sodium hydroxide; sodium tetrahydroborate; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; <(n-Bu3P)3CuI>4; sulfuric acid; dihydrogen peroxide; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ja961071u