(4R,5S,6R)-4-((S)-1-{2-[(2R,3S,4R)-2,4-bis(tert-butyldimethylsilanyloxy)-3,5-dimethylhexyl]-[1,3]dithian-2-yl}-ethyl)-6-(tert-butyldiphenylsilanyloxymethyl)-2,2,5-trimethyl-[1,3]dioxane

Base Information

• Chemical Name: (4R,5S,6R)-4-((S)-1-{2-[(2R,3S,4R)-2,4-bis(tert-butyldimethylsilanyloxy)-3,5-dimethylhexyl]-[1,3]dithian-2-yl}-ethyl)-6-(tert-butyldiphenylsilanyloxymethyl)-2,2,5-trimethyl-[1,3]dioxane
• CAS No.: 381246-83-9
• Molecular Formula: C₅₀H₈₈O₅S₂Si₃
• Molecular Weight: 917.634

Synonyms:(4R,5S,6R)-4-((S)-1-{2-[(2R,3S,4R)-2,4-bis(tert-butyldimethylsilanyloxy)-3,5-dimethylhexyl]-[1,3]dithian-2-yl}-ethyl)-6-(tert-butyldiphenylsilanyloxymethyl)-2,2,5-trimethyl-[1,3]dioxane

Chemical Property of (4R,5S,6R)-4-((S)-1-{2-[(2R,3S,4R)-2,4-bis(tert-butyldimethylsilanyloxy)-3,5-dimethylhexyl]-[1,3]dithian-2-yl}-ethyl)-6-(tert-butyldiphenylsilanyloxymethyl)-2,2,5-trimethyl-[1,3]dioxane

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Technology Process of (4R,5S,6R)-4-((S)-1-{2-[(2R,3S,4R)-2,4-bis(tert-butyldimethylsilanyloxy)-3,5-dimethylhexyl]-[1,3]dithian-2-yl}-ethyl)-6-(tert-butyldiphenylsilanyloxymethyl)-2,2,5-trimethyl-[1,3]dioxane

There total 22 articles about (4R,5S,6R)-4-((S)-1-{2-[(2R,3S,4R)-2,4-bis(tert-butyldimethylsilanyloxy)-3,5-dimethylhexyl]-[1,3]dithian-2-yl}-ethyl)-6-(tert-butyldiphenylsilanyloxymethyl)-2,2,5-trimethyl-[1,3]dioxane 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:

D-Val-OH (640-68-6,25609-85-2,7004-03-7,921-10-8) → (4R,5S,6R)-4-((S)-1-{2-[(2R,3S,4R)-2,4-bis(tert-butyldimethylsilanyloxy)-3,5-dimethylhexyl]-[1,3]dithian-2-yl}-ethyl)-6-(tert-butyldiphenylsilanyloxymethyl)-2,2,5-trimethyl-[1,3]dioxane (381246-83-9)

Guidance literature:

Multi-step reaction with 16 steps

1.1: NaNO₂; aq. H₂SO₄

2.1: 85 percent / iPr₂NEt / CH₂Cl₂ / 52 h / 20 °C

3.1: 87 percent / DIBAL-H / tetrahydrofuran / 3 h / 0 °C

4.1: oxalyl chloride; DMSO; diisopropylethylamine / CH₂Cl₂ / -55 - 130 °C

5.1: 7.0 g / CH₂Cl₂ / 14 h / 20 °C

6.1: 90 percent / TMSCl / tetrahydrofuran; diethyl ether / 3.5 h / -78 °C

7.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

7.2: 80 percent / trans-2-phenyl-sulfonyl-3-phenyloxaziridine / tetrahydrofuran; toluene / 3 h / -78 °C

8.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

9.1: 86 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / 0 °C

10.1: 88 percent / DMAP / CH₂Cl₂ / 12 h / 0 °C

11.1: H₂ / Pd(OH)2/C / methanol / 6 h / 20 °C / 760.05 Torr

12.1: 2.86 g / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

13.1: 91 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / -78 °C

14.1: 84 percent / I₂; imidazole; PPh₃ / toluene / 1.5 h / 0 °C

15.1: t-BuLi; HMPA / tetrahydrofuran; pentane / 1 h / -78 °C

15.2: 81 percent / tetrahydrofuran; pentane / 2 h / -78 °C

With 1H-imidazole; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; chloro-trimethyl-silane; oxalyl dichloride; sulfuric acid; hydrogen; iodine; tert.-butyl lithium; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium nitrite; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; pentane; 5.1: Swern oxidation;

DOI:10.1021/ja011452u

Reference yield:

(R)-2-Hydroxy-3-methylbutyric acid (17407-56-6) → (4R,5S,6R)-4-((S)-1-{2-[(2R,3S,4R)-2,4-bis(tert-butyldimethylsilanyloxy)-3,5-dimethylhexyl]-[1,3]dithian-2-yl}-ethyl)-6-(tert-butyldiphenylsilanyloxymethyl)-2,2,5-trimethyl-[1,3]dioxane (381246-83-9)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 85 percent / iPr₂NEt / CH₂Cl₂ / 52 h / 20 °C

2.1: 87 percent / DIBAL-H / tetrahydrofuran / 3 h / 0 °C

3.1: oxalyl chloride; DMSO; diisopropylethylamine / CH₂Cl₂ / -55 - 130 °C

4.1: 7.0 g / CH₂Cl₂ / 14 h / 20 °C

5.1: 90 percent / TMSCl / tetrahydrofuran; diethyl ether / 3.5 h / -78 °C

6.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

6.2: 80 percent / trans-2-phenyl-sulfonyl-3-phenyloxaziridine / tetrahydrofuran; toluene / 3 h / -78 °C

7.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

8.1: 86 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / 0 °C

9.1: 88 percent / DMAP / CH₂Cl₂ / 12 h / 0 °C

10.1: H₂ / Pd(OH)2/C / methanol / 6 h / 20 °C / 760.05 Torr

11.1: 2.86 g / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

12.1: 91 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / -78 °C

13.1: 84 percent / I₂; imidazole; PPh₃ / toluene / 1.5 h / 0 °C

14.1: t-BuLi; HMPA / tetrahydrofuran; pentane / 1 h / -78 °C

14.2: 81 percent / tetrahydrofuran; pentane / 2 h / -78 °C

With 1H-imidazole; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; chloro-trimethyl-silane; oxalyl dichloride; hydrogen; iodine; tert.-butyl lithium; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; pentane; 4.1: Swern oxidation;

DOI:10.1021/ja011452u

Reference yield:

(R)-methyl 2-hydroxy-3-methylbutanoate (90244-32-9) → (4R,5S,6R)-4-((S)-1-{2-[(2R,3S,4R)-2,4-bis(tert-butyldimethylsilanyloxy)-3,5-dimethylhexyl]-[1,3]dithian-2-yl}-ethyl)-6-(tert-butyldiphenylsilanyloxymethyl)-2,2,5-trimethyl-[1,3]dioxane (381246-83-9)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 85 percent / iPr₂NEt / CH₂Cl₂ / 52 h / 20 °C

2.1: 87 percent / DIBAL-H / tetrahydrofuran / 3 h / 0 °C

3.1: oxalyl chloride; DMSO; diisopropylethylamine / CH₂Cl₂ / -55 - 130 °C

4.1: 7.0 g / CH₂Cl₂ / 14 h / 20 °C

5.1: 90 percent / TMSCl / tetrahydrofuran; diethyl ether / 3.5 h / -78 °C

6.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / -78 °C

6.2: 80 percent / trans-2-phenyl-sulfonyl-3-phenyloxaziridine / tetrahydrofuran; toluene / 3 h / -78 °C

7.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

8.1: 86 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / 0 °C

9.1: 88 percent / DMAP / CH₂Cl₂ / 12 h / 0 °C

10.1: H₂ / Pd(OH)2/C / methanol / 6 h / 20 °C / 760.05 Torr

11.1: 2.86 g / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

12.1: 91 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / -78 °C

13.1: 84 percent / I₂; imidazole; PPh₃ / toluene / 1.5 h / 0 °C

14.1: t-BuLi; HMPA / tetrahydrofuran; pentane / 1 h / -78 °C

14.2: 81 percent / tetrahydrofuran; pentane / 2 h / -78 °C

With 1H-imidazole; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; chloro-trimethyl-silane; oxalyl dichloride; hydrogen; iodine; tert.-butyl lithium; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; pentane; 3.1: Swern oxidation;

DOI:10.1021/ja011452u

upstream raw materials:

D-Val-OH

(R)-2-Hydroxy-3-methylbutyric acid

(R)-methyl 2-hydroxy-3-methylbutanoate

(2R,3R,4R,5S,6S)-6-[(benzyloxy)methoxy]-7-(tert-butyldiphenylsilanyloxy)-2-hydroxy-4-methoxymethoxy-3,5-dimethylheptanoic acid methyl ester

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