(3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-{(2R,6S)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-butyl]-tetrahydro-pyran-2-yl}-hexanoic acid

Base Information

Chemical Name:(3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-{(2R,6S)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-butyl]-tetrahydro-pyran-2-yl}-hexanoic acid
CAS No.:915106-52-4
Molecular Formula:C₄₃H₇₄O₇Si₃
Molecular Weight:787.313
Hs Code.:

(3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-{(2R,6S)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-butyl]-tetrahydro-pyran-2-yl}-hexanoic acid

Synonyms:(3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-{(2R,6S)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-butyl]-tetrahydro-pyran-2-yl}-hexanoic acid

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Chemical Property of (3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-{(2R,6S)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-butyl]-tetrahydro-pyran-2-yl}-hexanoic acid

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Technology Process of (3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-{(2R,6S)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-butyl]-tetrahydro-pyran-2-yl}-hexanoic acid

There total 7 articles about (3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-{(2R,6S)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-butyl]-tetrahydro-pyran-2-yl}-hexanoic acid 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: 92.0%

: 915106-61-5
(3R,5R)-6-{(2R,6S)-6-[(S)-4-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxy)-butyl]-tetrahydro-pyran-2-yl}-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-hexanoic acid

: 915106-52-4
(3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-{(2R,6S)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-butyl]-tetrahydro-pyran-2-yl}-hexanoic acid

Guidance literature:: With hydrogen; palladium dihydroxide; In tetrahydrofuran; at 20 ℃; for 3h; under 12411.6 Torr;
DOI:10.1021/ol0620904

Reference yield:

: 915106-48-8
(R)-4-{(2R,6S)-6-[(S)-4-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxy)-butyl]-tetrahydro-pyran-2-yl}-3-(tert-butyl-dimethyl-silanyloxy)-butyraldehyde

: 915106-52-4
(3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-{(2R,6S)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-butyl]-tetrahydro-pyran-2-yl}-hexanoic acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: (-)-(IPC)2BOMe / diethyl ether / 1 h / -78 - 20 °C

1.2: 69 percent / diethyl ether / 2.5 h / -78 °C

2.1: 89 percent / imidazole / dimethylformamide / 7 h / 20 °C

3.1: 67 percent / NaIO₄; KMnO₄ / 2-methyl-propan-2-ol; H₂O / 0.75 h / 20 °C / pH 7

4.1: 92 percent / H₂ / Pd(OH)2/C / tetrahydrofuran / 3 h / 20 °C / 12411.6 Torr

With 1H-imidazole; potassium permanganate; sodium periodate; hydrogen; (-)-B-methoxydiisopinocampheylborane; palladium dihydroxide; In tetrahydrofuran; diethyl ether; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1.2: Brown's allylation;
DOI:10.1021/ol0620904

Reference yield:

: 915106-70-6
(S)-4-{(2R,6S)-6-[(S)-4-Benzyloxy-2-(tert-butyl-diphenyl-silanyloxy)-butyl]-tetrahydro-pyran-2-yl}-3-(tert-butyl-dimethyl-silanyloxy)-butan-1-ol

: 915106-52-4
(3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-{(2R,6S)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-butyl]-tetrahydro-pyran-2-yl}-hexanoic acid

Guidance literature:: Multi-step reaction with 5 steps

1.1: 90 percent / NaHCO₃; Dess-Martin periodinane / tetrahydrofuran / 1.5 h / 20 °C

2.1: (-)-(IPC)2BOMe / diethyl ether / 1 h / -78 - 20 °C

2.2: 69 percent / diethyl ether / 2.5 h / -78 °C

3.1: 89 percent / imidazole / dimethylformamide / 7 h / 20 °C

4.1: 67 percent / NaIO₄; KMnO₄ / 2-methyl-propan-2-ol; H₂O / 0.75 h / 20 °C / pH 7

5.1: 92 percent / H₂ / Pd(OH)2/C / tetrahydrofuran / 3 h / 20 °C / 12411.6 Torr

With 1H-imidazole; potassium permanganate; sodium periodate; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; (-)-B-methoxydiisopinocampheylborane; palladium dihydroxide; In tetrahydrofuran; diethyl ether; water; N,N-dimethyl-formamide; tert-butyl alcohol; 2.2: Brown's allylation;
DOI:10.1021/ol0620904