(5S,6S)-6-[(1S,4S,5R,6R)-6-(tert-butyldiphenylsilyloxy)-4-hydroxy-1,5-dimethyl-oct-7-ynyl]-5-methyl-5,6-dihydro-pyran-2-one

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Chemical Name:(5S,6S)-6-[(1S,4S,5R,6R)-6-(tert-butyldiphenylsilyloxy)-4-hydroxy-1,5-dimethyl-oct-7-ynyl]-5-methyl-5,6-dihydro-pyran-2-one
CAS No.:455948-95-5
Molecular Formula:C₃₂H₄₂O₄Si
Molecular Weight:518.769
Hs Code.:

Synonyms:(5S,6S)-6-[(1S,4S,5R,6R)-6-(tert-butyldiphenylsilyloxy)-4-hydroxy-1,5-dimethyl-oct-7-ynyl]-5-methyl-5,6-dihydro-pyran-2-one

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Chemical Property of (5S,6S)-6-[(1S,4S,5R,6R)-6-(tert-butyldiphenylsilyloxy)-4-hydroxy-1,5-dimethyl-oct-7-ynyl]-5-methyl-5,6-dihydro-pyran-2-one

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Technology Process of (5S,6S)-6-[(1S,4S,5R,6R)-6-(tert-butyldiphenylsilyloxy)-4-hydroxy-1,5-dimethyl-oct-7-ynyl]-5-methyl-5,6-dihydro-pyran-2-one

There total 20 articles about (5S,6S)-6-[(1S,4S,5R,6R)-6-(tert-butyldiphenylsilyloxy)-4-hydroxy-1,5-dimethyl-oct-7-ynyl]-5-methyl-5,6-dihydro-pyran-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: 83.0%

: 455948-94-4
methyl (4S,5S,6S,9S,10S,11R)-11-(tert-butyldiphenylsilyloxy)-5,9-bis(methoxymethoxy)-4,6,10-trimethyl-tridec-2-en-12-ynoate

: 455948-95-5
(5S,6S)-6-[(1S,4S,5R,6R)-6-(tert-butyldiphenylsilyloxy)-4-hydroxy-1,5-dimethyl-oct-7-ynyl]-5-methyl-5,6-dihydro-pyran-2-one

Guidance literature:: With carbon tetrabromide; In isopropyl alcohol; at 82 ℃;
DOI:10.1002/1521-3773(20020517)41:10<1748::AID-ANIE1748>3.0.CO;2-X

Reference yield:

: 750646-35-6
(4S,5S,6S)-7-(tert-Butyl-dimethyl-silanyloxy)-5-methoxymethoxy-4,6-dimethyl-heptanal

: 455948-95-5
(5S,6S)-6-[(1S,4S,5R,6R)-6-(tert-butyldiphenylsilyloxy)-4-hydroxy-1,5-dimethyl-oct-7-ynyl]-5-methyl-5,6-dihydro-pyran-2-one

Guidance literature:: Multi-step reaction with 11 steps

1.1: (i-Pr)2NEt; dibutylboryltriflate / CH₂Cl₂ / 1 h / 0 °C

1.2: CH₂Cl₂ / 3 h / -78 - 20 °C

1.3: 89 percent / aq. H₂O₂ / 1.5 h / 20 °C

2.1: 97 percent / N,N-dimethylaminopyridine; Et₃N / CH₂Cl₂ / 15.5 h / 0 - 20 °C

3.1: Me₃Al / toluene; tetrahydrofuran / 0.5 h / 20 °C

3.2: 84 percent / toluene; tetrahydrofuran / 15.5 h / -20 - 0 °C

4.1: 94 percent / (i-Pr)2NEt / CH₂Cl₂ / 19 h / 0 - 20 °C

5.1: n-BuLi / hexane; tetrahydrofuran / 1.25 h / -78 - 20 °C

5.2: hexane; tetrahydrofuran / 1.25 h / -10 °C

5.3: 2.64 g / aq. disodium tetraborate / methanol / 1.33 h / -10 - 20 °C

6.1: 89 percent / (R)-2-methyl-CBS-oxazaborolidine; BH₃*Me₂S / tetrahydrofuran; toluene / 1 h / -30 °C

7.1: imidazole / dimethylformamide / 15 h / 20 °C

8.1: 2.43 g / HF/pyridine / tetrahydrofuran / 0.67 h / 20 °C

9.1: 93 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1.42 h / 20 °C

10.1: KHMDS; [18]crown-6 / toluene; tetrahydrofuran / 0.58 h / -78 °C

10.2: 2.05 g / toluene; tetrahydrofuran / 4.33 h / -78 °C

11.1: 83 percent / CBr₄ / propan-2-ol / 15 h / 82 °C

With pyridine; 1H-imidazole; dmap; n-butyllithium; 18-crown-6 ether; carbon tetrabromide; dimethylsulfide borane complex; di-n-butylboryl trifluoromethanesulfonate; hydrogen fluoride; trimethylaluminum; potassium hexamethylsilazane; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; toluene; 1.1: Evans aldol reaction / 9.1: Dess-Martin oxidation / 10.2: Still-Gennari olefination;
DOI:10.1002/chem.200305543

Reference yield:

: 455949-00-5
(2S,3S,4S)-3-(methoxymethoxy)-2,4-dimethylhept-6-en-1-ol

: 455948-95-5
(5S,6S)-6-[(1S,4S,5R,6R)-6-(tert-butyldiphenylsilyloxy)-4-hydroxy-1,5-dimethyl-oct-7-ynyl]-5-methyl-5,6-dihydro-pyran-2-one

Guidance literature:: Multi-step reaction with 14 steps

1.1: 100 percent / imidazole / dimethylformamide / 15 h / 20 °C

2.1: 9-BBN / tetrahydrofuran / 15 h / 20 °C

2.2: 83 percent / aq. NaOH; H₂O₂ / 24 h / 20 °C

3.1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 2.5 h / -78 - 0 °C

4.1: (i-Pr)2NEt; dibutylboryltriflate / CH₂Cl₂ / 1 h / 0 °C

4.2: CH₂Cl₂ / 3 h / -78 - 20 °C

4.3: 89 percent / aq. H₂O₂ / 1.5 h / 20 °C

5.1: 97 percent / N,N-dimethylaminopyridine; Et₃N / CH₂Cl₂ / 15.5 h / 0 - 20 °C

6.1: Me₃Al / toluene; tetrahydrofuran / 0.5 h / 20 °C

6.2: 84 percent / toluene; tetrahydrofuran / 15.5 h / -20 - 0 °C

7.1: 94 percent / (i-Pr)2NEt / CH₂Cl₂ / 19 h / 0 - 20 °C

8.1: n-BuLi / hexane; tetrahydrofuran / 1.25 h / -78 - 20 °C

8.2: hexane; tetrahydrofuran / 1.25 h / -10 °C

8.3: 2.64 g / aq. disodium tetraborate / methanol / 1.33 h / -10 - 20 °C

9.1: 89 percent / (R)-2-methyl-CBS-oxazaborolidine; BH₃*Me₂S / tetrahydrofuran; toluene / 1 h / -30 °C

10.1: imidazole / dimethylformamide / 15 h / 20 °C

11.1: 2.43 g / HF/pyridine / tetrahydrofuran / 0.67 h / 20 °C

12.1: 93 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1.42 h / 20 °C

13.1: KHMDS; [18]crown-6 / toluene; tetrahydrofuran / 0.58 h / -78 °C

13.2: 2.05 g / toluene; tetrahydrofuran / 4.33 h / -78 °C

14.1: 83 percent / CBr₄ / propan-2-ol / 15 h / 82 °C

With pyridine; 1H-imidazole; dmap; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; oxalyl dichloride; 18-crown-6 ether; carbon tetrabromide; dimethylsulfide borane complex; di-n-butylboryl trifluoromethanesulfonate; hydrogen fluoride; trimethylaluminum; potassium hexamethylsilazane; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; toluene; 3.1: Swern oxidation / 4.1: Evans aldol reaction / 12.1: Dess-Martin oxidation / 13.2: Still-Gennari olefination;
DOI:10.1002/chem.200305543