(4R,6R)-6-(tert-butyldimethylsiloxy)-1-(tert-butyldiphenylsiloxy)-4-(4-methoxybenzyloxy)-7-octyn-3-one

Base Information

Chemical Name:(4R,6R)-6-(tert-butyldimethylsiloxy)-1-(tert-butyldiphenylsiloxy)-4-(4-methoxybenzyloxy)-7-octyn-3-one
CAS No.:902782-09-6
Molecular Formula:C₃₈H₅₂O₅Si₂
Molecular Weight:644.999
Hs Code.:

Synonyms:(4R,6R)-6-(tert-butyldimethylsiloxy)-1-(tert-butyldiphenylsiloxy)-4-(4-methoxybenzyloxy)-7-octyn-3-one

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Chemical Property of (4R,6R)-6-(tert-butyldimethylsiloxy)-1-(tert-butyldiphenylsiloxy)-4-(4-methoxybenzyloxy)-7-octyn-3-one

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Technology Process of (4R,6R)-6-(tert-butyldimethylsiloxy)-1-(tert-butyldiphenylsiloxy)-4-(4-methoxybenzyloxy)-7-octyn-3-one

There total 11 articles about (4R,6R)-6-(tert-butyldimethylsiloxy)-1-(tert-butyldiphenylsiloxy)-4-(4-methoxybenzyloxy)-7-octyn-3-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:

: 902782-31-4
(2E,5R,6E)-5-(4-methoxybenzyloxy)-2,6-octadien-1-ol

: 902782-09-6
(4R,6R)-6-(tert-butyldimethylsiloxy)-1-(tert-butyldiphenylsiloxy)-4-(4-methoxybenzyloxy)-7-octyn-3-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: 93 percent / tBuOOH; molecular sieves 4 Angstroem; D-(-)-diisopropyl tartrate / Ti(O-iPr)4 / CH₂Cl₂ / 10 h / -20 °C

2.1: 88 percent / PPh₃; CCl₄; NaHCO₃ / 3 h / Heating

3.1: nBuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

4.1: 9.22 g / imidazole / dimethylformamide / 1 h / 20 °C

5.1: O₃; 2,6-lutidine / methanol / 2 h / -78 °C

5.2: Me₂S / methanol / 1 h / 20 °C

6.1: iPr₂NLi / tetrahydrofuran; hexane / 1 h / -78 °C

6.2: tetrahydrofuran; hexane / 0.5 h / -78 °C

7.1: 8.42 g / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

8.1: imidazole / dimethylformamide / 1 h / 20 °C

9.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.5 h

With 1H-imidazole; 2,6-dimethylpyridine; tert.-butylhydroperoxide; tetrachloromethane; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; 4 A molecular sieve; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; ozone; dimethyl sulfoxide; triethylamine; triphenylphosphine; lithium diisopropyl amide; titanium(IV) isopropylate; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: Sharpless asymmetric epoxidation / 9.1: Swern oxidation;
DOI:10.1002/anie.200600458

Reference yield:

: 902782-29-0
C₁₆H₂₂O₄

: 902782-09-6
(4R,6R)-6-(tert-butyldimethylsiloxy)-1-(tert-butyldiphenylsiloxy)-4-(4-methoxybenzyloxy)-7-octyn-3-one

Guidance literature:: Multi-step reaction with 13 steps

1.1: 17.3 g / LiAlH₄ / tetrahydrofuran / 1 h / 20 °C

2.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -40 °C

3.1: LiCl; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 0.5 h / 0 °C

3.2: 15.7 g / acetonitrile / 1 h / 20 °C

4.1: 96 percent / diisobutylaluminium hydride / tetrahydrofuran; hexane / 1 h / -78 - -60 °C

5.1: 93 percent / tBuOOH; molecular sieves 4 Angstroem; D-(-)-diisopropyl tartrate / Ti(O-iPr)4 / CH₂Cl₂ / 10 h / -20 °C

6.1: 88 percent / PPh₃; CCl₄; NaHCO₃ / 3 h / Heating

7.1: nBuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

8.1: 9.22 g / imidazole / dimethylformamide / 1 h / 20 °C

9.1: O₃; 2,6-lutidine / methanol / 2 h / -78 °C

9.2: Me₂S / methanol / 1 h / 20 °C

10.1: iPr₂NLi / tetrahydrofuran; hexane / 1 h / -78 °C

10.2: tetrahydrofuran; hexane / 0.5 h / -78 °C

11.1: 8.42 g / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

12.1: imidazole / dimethylformamide / 1 h / 20 °C

13.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.5 h

With 1H-imidazole; 2,6-dimethylpyridine; tert.-butylhydroperoxide; tetrachloromethane; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; 4 A molecular sieve; diisobutylaluminium hydride; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; ozone; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; lithium chloride; lithium diisopropyl amide; titanium(IV) isopropylate; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 2.1: Swern oxidation / 3.2: Horner-Wadsworth-Emmons reaction / 5.1: Sharpless asymmetric epoxidation / 13.1: Swern oxidation;
DOI:10.1002/anie.200600458

Reference yield:

: 902782-30-3
C₁₄H₁₈O₃

: 902782-09-6
(4R,6R)-6-(tert-butyldimethylsiloxy)-1-(tert-butyldiphenylsiloxy)-4-(4-methoxybenzyloxy)-7-octyn-3-one

Guidance literature:: Multi-step reaction with 11 steps

1.1: LiCl; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 0.5 h / 0 °C

1.2: 15.7 g / acetonitrile / 1 h / 20 °C

2.1: 96 percent / diisobutylaluminium hydride / tetrahydrofuran; hexane / 1 h / -78 - -60 °C

3.1: 93 percent / tBuOOH; molecular sieves 4 Angstroem; D-(-)-diisopropyl tartrate / Ti(O-iPr)4 / CH₂Cl₂ / 10 h / -20 °C

4.1: 88 percent / PPh₃; CCl₄; NaHCO₃ / 3 h / Heating

5.1: nBuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

6.1: 9.22 g / imidazole / dimethylformamide / 1 h / 20 °C

7.1: O₃; 2,6-lutidine / methanol / 2 h / -78 °C

7.2: Me₂S / methanol / 1 h / 20 °C

8.1: iPr₂NLi / tetrahydrofuran; hexane / 1 h / -78 °C

8.2: tetrahydrofuran; hexane / 0.5 h / -78 °C

9.1: 8.42 g / LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

10.1: imidazole / dimethylformamide / 1 h / 20 °C

11.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.5 h

With 1H-imidazole; 2,6-dimethylpyridine; tert.-butylhydroperoxide; tetrachloromethane; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; 4 A molecular sieve; diisobutylaluminium hydride; sodium hydrogencarbonate; D-(-)-diisopropyl tartrate; ozone; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; lithium chloride; lithium diisopropyl amide; titanium(IV) isopropylate; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1.2: Horner-Wadsworth-Emmons reaction / 3.1: Sharpless asymmetric epoxidation / 11.1: Swern oxidation;
DOI:10.1002/anie.200600458