(13S)-2-t-butoxycarbonyl-6-hydroxy-8-(t-butyldiphenylsilyloxy)-13-isopropenyl-4,9-cyclotetradecadiynone

Base Information

• Chemical Name: (13S)-2-t-butoxycarbonyl-6-hydroxy-8-(t-butyldiphenylsilyloxy)-13-isopropenyl-4,9-cyclotetradecadiynone
• CAS No.: 392686-86-1
• Molecular Formula: C₃₈H₄₈O₅Si
• Molecular Weight: 612.882
• Mol file: 392686-86-1.mol

Synonyms:(13S)-2-t-butoxycarbonyl-6-hydroxy-8-(t-butyldiphenylsilyloxy)-13-isopropenyl-4,9-cyclotetradecadiynone

Chemical Property of (13S)-2-t-butoxycarbonyl-6-hydroxy-8-(t-butyldiphenylsilyloxy)-13-isopropenyl-4,9-cyclotetradecadiynone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (13S)-2-t-butoxycarbonyl-6-hydroxy-8-(t-butyldiphenylsilyloxy)-13-isopropenyl-4,9-cyclotetradecadiynone

There total 16 articles about (13S)-2-t-butoxycarbonyl-6-hydroxy-8-(t-butyldiphenylsilyloxy)-13-isopropenyl-4,9-cyclotetradecadiynone 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: 80.0%

(13S)-2-t-butoxycarbonyl-6-(t-butyldimethylsilyloxy)-8-(t-butyldiphenylsilyloxy)-13-isopropenyl-4,9-cyclotetradecadiynone (392686-85-0) → (13S)-2-t-butoxycarbonyl-6-hydroxy-8-(t-butyldiphenylsilyloxy)-13-isopropenyl-4,9-cyclotetradecadiynone (392686-86-1)

Guidance literature:

With pyridinium p-toluenesulfonate; In ethanol; at 20 ℃; for 240h;

DOI:10.1021/jo016048s

Reference yield:

(-)-perillyl alcohol (536-59-4,18457-55-1) → (13S)-2-t-butoxycarbonyl-6-hydroxy-8-(t-butyldiphenylsilyloxy)-13-isopropenyl-4,9-cyclotetradecadiynone (392686-86-1)

Guidance literature:

Multi-step reaction with 16 steps

1.1: 98 percent / VO(acac)2; tert-butyl hydroperoxide / CH₂Cl₂; various solvent(s) / 1 h / 0 °C

2.1: H₅IO₆ / tetrahydrofuran / 0.25 h / 0 °C

2.2: 75 percent / p-TsOH / methanol / Heating

3.1: 97 percent / DIBAL-H / various solvent(s) / 1 h / -78 °C

4.1: 85 percent / K₂CO₃ / methanol / 2 h / 20 °C

5.1: BuLi / tetrahydrofuran; various solvent(s) / 1 h / -40 °C

5.2: LiBr / tetrahydrofuran; various solvent(s) / 0.25 h

5.3: 84 percent / tetrahydrofuran; various solvent(s) / -40 - -30 °C

6.1: 97 percent / imidazole / dimethylformamide / 20 °C

7.1: 96 percent / pyridinium p-toluenesulfonate / methanol / 20 °C

8.1: 100 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1.5 h

9.1: BuLi / tetrahydrofuran; various solvent(s) / 1 h / -40 °C

9.2: LiBr / tetrahydrofuran; various solvent(s) / 0.25 h

9.3: 88 percent / tetrahydrofuran; various solvent(s) / -40 - -30 °C

10.1: 99 percent / p-TsOH / acetone; H₂O / 48 h / 20 °C

11.1: 91 percent / imidazole / dimethylformamide / 20 °C

12.1: 85 percent / SnCl₂ / CH₂Cl₂ / 2 h / 20 °C

13.1: 85 percent / DDQ / CH₂Cl₂ / 6 h / 20 °C / pH 7

14.1: I₂; triphenylphosphine; imidazole / diethyl ether; benzene / 0.75 h / 20 °C

15.1: 83 percent / t-BuOK / tetrahydrofuran / -78 - 20 °C

16.1: 80 percent / pyridinium p-toluenesulfonate / ethanol / 240 h / 20 °C

With 1H-imidazole; tert.-butylhydroperoxide; n-butyllithium; bis(acetylacetonate)oxovanadium; potassium tert-butylate; iodine; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; periodic acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tin(ll) chloride; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1021/jo016048s

Reference yield:

((4S)-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-1-yl)methanol (190718-78-6) → (13S)-2-t-butoxycarbonyl-6-hydroxy-8-(t-butyldiphenylsilyloxy)-13-isopropenyl-4,9-cyclotetradecadiynone (392686-86-1)

Guidance literature:

Multi-step reaction with 15 steps

1.1: H₅IO₆ / tetrahydrofuran / 0.25 h / 0 °C

1.2: 75 percent / p-TsOH / methanol / Heating

2.1: 97 percent / DIBAL-H / various solvent(s) / 1 h / -78 °C

3.1: 85 percent / K₂CO₃ / methanol / 2 h / 20 °C

4.1: BuLi / tetrahydrofuran; various solvent(s) / 1 h / -40 °C

4.2: LiBr / tetrahydrofuran; various solvent(s) / 0.25 h

4.3: 84 percent / tetrahydrofuran; various solvent(s) / -40 - -30 °C

5.1: 97 percent / imidazole / dimethylformamide / 20 °C

6.1: 96 percent / pyridinium p-toluenesulfonate / methanol / 20 °C

7.1: 100 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1.5 h

8.1: BuLi / tetrahydrofuran; various solvent(s) / 1 h / -40 °C

8.2: LiBr / tetrahydrofuran; various solvent(s) / 0.25 h

8.3: 88 percent / tetrahydrofuran; various solvent(s) / -40 - -30 °C

9.1: 99 percent / p-TsOH / acetone; H₂O / 48 h / 20 °C

10.1: 91 percent / imidazole / dimethylformamide / 20 °C

11.1: 85 percent / SnCl₂ / CH₂Cl₂ / 2 h / 20 °C

12.1: 85 percent / DDQ / CH₂Cl₂ / 6 h / 20 °C / pH 7

13.1: I₂; triphenylphosphine; imidazole / diethyl ether; benzene / 0.75 h / 20 °C

14.1: 83 percent / t-BuOK / tetrahydrofuran / -78 - 20 °C

15.1: 80 percent / pyridinium p-toluenesulfonate / ethanol / 240 h / 20 °C

With 1H-imidazole; n-butyllithium; potassium tert-butylate; iodine; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; periodic acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tin(ll) chloride; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1021/jo016048s

upstream raw materials:

(13S)-2-t-butoxycarbonyl-6-(t-butyldimethylsilyloxy)-8-(t-butyldiphenylsilyloxy)-13-isopropenyl-4,9-cyclotetradecadiynone

(-)-perillyl alcohol

((4S)-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-1-yl)methanol

(S)-7,7-dimethoxy-5-isopropenyl-1-heptyne

Downstream raw materials:

5-(tert-butyl-diphenyl-silanyloxy)-10-isopropenyl-3-oxo-15-oxa-bicyclo[10.2.1]pentadeca-1⁽¹⁴⁾,12-dien-6-yne-13-carboxylic acid tert-butyl ester

(13S)-2-t-butoxycarbonyl-8-(t-butyldiphenylsilyloxy)-13-isopropenyl-4,9-cyclotetradecadiyne-1,6-dione