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

Base Information

• Chemical Name: 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
• CAS No.: 114066-21-6
• Molecular Formula: C₃₆H₅₂O₅Si
• Molecular Weight: 592.891

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of 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

There total 23 articles about 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 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: 89.0%

[(2S,4S,6R,8R,9S)-4-(tert-Butyl-diphenyl-silanyloxy)-8-isopropyl-9-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-acetaldehyde (114099-52-4) + (carbethoxyethylidene)triphenylphosphorane (21382-82-1) → 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 (114066-21-6)

Guidance literature:

In benzene; at 80 ℃; for 1h; Heating;

DOI:10.1016/S0040-4039(00)96346-9

Reference yield:

5(S)-methyl-6(R)-isopropyltetrahydro-2(3H)-pyranone (114179-37-2) → 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 (114066-21-6)

Guidance literature:

Multi-step reaction with 10 steps

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

2: 88 percent / K₂CO₃ / 16 h / Ambient temperature

3: TsOH / tetrahydrofuran; H₂O

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

5: 25 percent / NaBH₄ / 1,2-dimethoxy-ethane / 1 h

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

7: 100 percent / imidazole, 4-(dimethylamino)pyridine / dimethylformamide / 60 h / 25 °C

8: 1.) 9-BBN, 2.) aq. H₂O₂, aq. NaOH / 1.) THF, irradiation, 1 h, 2.) THF, 3 h

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

10: 89 percent / CH₂Cl₂ / 16 h / Heating

With 1H-imidazole; chromium(VI) oxide; dmap; sodium hydroxide; sodium tetrahydroborate; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; oxalyl dichloride; <(n-Bu3P)3CuI>4; sulfuric acid; dihydrogen peroxide; 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:

1-hydroxy-1(R)-isopropyl-9-methoxy-2(S)-methylnon-8-en-6-yn-5-one (114066-14-7) → 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 (114066-21-6)

Guidance literature:

Multi-step reaction with 9 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

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; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/ja961071u

upstream raw materials:

[(2S,4S,6R,8R,9S)-4-(tert-Butyl-diphenyl-silanyloxy)-8-isopropyl-9-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-acetaldehyde

(carbethoxyethylidene)triphenylphosphorane

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

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

Downstream 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

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

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

C₃₉H₅₂O₆S

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