(3R,4S,7R,11S,12S,15S)-1,16-bis-(tert-butyldimethylsilyloxy)-11,12-epoxy-3,7,11,15-tetramethyl-4-hexadecyl benzyl ether

Base Information

Chemical Name:(3R,4S,7R,11S,12S,15S)-1,16-bis-(tert-butyldimethylsilyloxy)-11,12-epoxy-3,7,11,15-tetramethyl-4-hexadecyl benzyl ether
CAS No.:1358982-95-2
Molecular Formula:C₃₉H₇₄O₄Si₂
Molecular Weight:663.185
Hs Code.:

Synonyms:(3R,4S,7R,11S,12S,15S)-1,16-bis-(tert-butyldimethylsilyloxy)-11,12-epoxy-3,7,11,15-tetramethyl-4-hexadecyl benzyl ether

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Chemical Property of (3R,4S,7R,11S,12S,15S)-1,16-bis-(tert-butyldimethylsilyloxy)-11,12-epoxy-3,7,11,15-tetramethyl-4-hexadecyl benzyl ether

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Technology Process of (3R,4S,7R,11S,12S,15S)-1,16-bis-(tert-butyldimethylsilyloxy)-11,12-epoxy-3,7,11,15-tetramethyl-4-hexadecyl benzyl ether

There total 20 articles about (3R,4S,7R,11S,12S,15S)-1,16-bis-(tert-butyldimethylsilyloxy)-11,12-epoxy-3,7,11,15-tetramethyl-4-hexadecyl benzyl ether 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:

: 1358982-15-6
(3R,4S,7R,11E,15S)-1,16-bis-(tert-butyldimethylsilyloxy)-3,7,11,15-tetramethyl-11-hexadecen-4-yl benzyl ether

: 1358982-95-2
(3R,4S,7R,11S,12S,15S)-1,16-bis-(tert-butyldimethylsilyloxy)-11,12-epoxy-3,7,11,15-tetramethyl-4-hexadecyl benzyl ether

: 1358982-45-2
(3R,4S,7R,11R,12R,15S)-1,16-bis-(tert-butyldimethylsilyloxy)-11,12-epoxy-3,7,11,15-tetramethyl-4-hexadecyl benzyl ether

Guidance literature:: With Shi's ketone; dihydrogen peroxide; potassium carbonate; In ethanol; dichloromethane; acetonitrile; at 0 ℃; optical yield given as %de; diastereoselective reaction; aq. buffer;
DOI:10.1016/j.bmc.2011.12.015

Reference yield:

: (S)-6-(4-methoxybenzyloxy)-4-methylhexanal

: 1358982-95-2
(3R,4S,7R,11S,12S,15S)-1,16-bis-(tert-butyldimethylsilyloxy)-11,12-epoxy-3,7,11,15-tetramethyl-4-hexadecyl benzyl ether

: 1358982-45-2
(3R,4S,7R,11R,12R,15S)-1,16-bis-(tert-butyldimethylsilyloxy)-11,12-epoxy-3,7,11,15-tetramethyl-4-hexadecyl benzyl ether

Guidance literature:: Multi-step reaction with 10 steps

1.1: n-butyllithium; potassium tert-butylate / tetrahydrofuran; hexane / 0.33 h / -78 - -45 °C

1.2: 1.08 h / -78 °C

2.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 - 20 °C

3.1: borane-THF / tetrahydrofuran / 2 h / 0 - 20 °C

3.2: 1 h / 20 °C

4.1: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 20 °C

5.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.75 h / 0 °C

6.1: tributylphosphine / N,N-dimethyl-formamide / 2 h / 0 - 20 °C

7.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.5 h / 0 °C

8.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C

8.2: 0.5 h / -78 °C

9.1: sodium amalgam; disodium hydrogenphosphate / tetrahydrofuran; methanol / 0.83 h / -15 - 20 °C

10.1: Shi's ketone; dihydrogen peroxide; potassium carbonate / ethanol; dichloromethane; acetonitrile / 0 °C / aq. buffer

With 1H-imidazole; disodium hydrogenphosphate; sodium amalgam; n-butyllithium; Shi's ketone; borane-THF; tributylphosphine; potassium tert-butylate; water; dihydrogen peroxide; sodium hydride; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 10.1: Shi epoxidation;
DOI:10.1016/j.bmc.2011.12.015

Reference yield:

: 934704-86-6
(S)-4-methoxybenzyl 3,7-dimethyl-6-octenyl ether

: 1358982-95-2
(3R,4S,7R,11S,12S,15S)-1,16-bis-(tert-butyldimethylsilyloxy)-11,12-epoxy-3,7,11,15-tetramethyl-4-hexadecyl benzyl ether

: 1358982-45-2
(3R,4S,7R,11R,12R,15S)-1,16-bis-(tert-butyldimethylsilyloxy)-11,12-epoxy-3,7,11,15-tetramethyl-4-hexadecyl benzyl ether

Guidance literature:: Multi-step reaction with 12 steps

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 0 °C

2.1: periodic acid / tetrahydrofuran; water / 2 h / 0 °C

3.1: n-butyllithium; potassium tert-butylate / tetrahydrofuran; hexane / 0.33 h / -78 - -45 °C

3.2: 1.08 h / -78 °C

4.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 - 20 °C

5.1: borane-THF / tetrahydrofuran / 2 h / 0 - 20 °C

5.2: 1 h / 20 °C

6.1: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 20 °C

7.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.75 h / 0 °C

8.1: tributylphosphine / N,N-dimethyl-formamide / 2 h / 0 - 20 °C

9.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.5 h / 0 °C

10.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C

10.2: 0.5 h / -78 °C

11.1: sodium amalgam; disodium hydrogenphosphate / tetrahydrofuran; methanol / 0.83 h / -15 - 20 °C

12.1: Shi's ketone; dihydrogen peroxide; potassium carbonate / ethanol; dichloromethane; acetonitrile / 0 °C / aq. buffer

With 1H-imidazole; disodium hydrogenphosphate; sodium amalgam; n-butyllithium; Shi's ketone; borane-THF; tributylphosphine; potassium tert-butylate; water; dihydrogen peroxide; sodium hydride; potassium carbonate; periodic acid; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 12.1: Shi epoxidation;
DOI:10.1016/j.bmc.2011.12.015