(2R,3S,6S)-1-tert-butyldiphenylsilyloxy-6-<(2R,5R,6S)-5-ethyl-5-methoxymethoxy-6-methyltetrahydropyran-2-yl>-3,6-bismethoxymethoxyheptan-2-ol

Base Information

• Chemical Name: (2R,3S,6S)-1-tert-butyldiphenylsilyloxy-6-<(2R,5R,6S)-5-ethyl-5-methoxymethoxy-6-methyltetrahydropyran-2-yl>-3,6-bismethoxymethoxyheptan-2-ol
• CAS No.: 126394-02-3
• Molecular Formula: C₃₇H₆₀O₉Si
• Molecular Weight: 676.963

Synonyms:(2R,3S,6S)-1-tert-butyldiphenylsilyloxy-6-<(2R,5R,6S)-5-ethyl-5-methoxymethoxy-6-methyltetrahydropyran-2-yl>-3,6-bismethoxymethoxyheptan-2-ol

Chemical Property of (2R,3S,6S)-1-tert-butyldiphenylsilyloxy-6-<(2R,5R,6S)-5-ethyl-5-methoxymethoxy-6-methyltetrahydropyran-2-yl>-3,6-bismethoxymethoxyheptan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,6S)-1-tert-butyldiphenylsilyloxy-6-<(2R,5R,6S)-5-ethyl-5-methoxymethoxy-6-methyltetrahydropyran-2-yl>-3,6-bismethoxymethoxyheptan-2-ol

There total 23 articles about (2R,3S,6S)-1-tert-butyldiphenylsilyloxy-6-<(2R,5R,6S)-5-ethyl-5-methoxymethoxy-6-methyltetrahydropyran-2-yl>-3,6-bismethoxymethoxyheptan-2-ol 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: 94.0%

(2R,3S,6S)-6-((2R,5R,6S)-5-Ethyl-5-methoxymethoxy-6-methyl-tetrahydro-pyran-2-yl)-3,6-bis-methoxymethoxy-heptane-1,2-diol (126394-01-2) + tert-butylchlorodiphenylsilane (58479-61-1) → (2R,3S,6S)-1-tert-butyldiphenylsilyloxy-6-<(2R,5R,6S)-5-ethyl-5-methoxymethoxy-6-methyltetrahydropyran-2-yl>-3,6-bismethoxymethoxyheptan-2-ol (126394-02-3)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 0 - 20 ℃;

DOI:10.1248/cpb.37.1705

Reference yield:

(2S,3R)-3-Benzyloxy-5-[(4R,5S)-5-but-3-enyl-2-(4-methoxy-phenyl)-2,5-dimethyl-[1,3]dioxolan-4-yl]-3-ethyl-pentan-2-ol (96823-48-2) → (2R,3S,6S)-1-tert-butyldiphenylsilyloxy-6-<(2R,5R,6S)-5-ethyl-5-methoxymethoxy-6-methyltetrahydropyran-2-yl>-3,6-bismethoxymethoxyheptan-2-ol (126394-02-3)

Guidance literature:

Multi-step reaction with 23 steps

1: 1) NaH / 1) THF, DMSO, RT, 2) THF, DMSO, RT, overnight

2: 81 percent / 1N HCl / tetrahydrofuran / 7.5 h / 45 °C

3: Et₃N / CH₂Cl₂ / 2 h / 0 °C

4: K₂CO₃ / methanol / 0.5 h / Ambient temperature

5: 90 percent / DDQ / H₂O; CH₂Cl₂ / 0.33 h / 0 °C

6: 90 percent / CSA / CH₂Cl₂ / 0.25 h / 0 °C

7: 96 percent / OsO₄, N-methylmorpholine N-oxide / acetone; H₂O / 0.5 h / Ambient temperature

8: hydrogen / Pd/C / ethanol / 72 h / Ambient temperature

9: 96 percent / NaIO₄ / tetrahydrofuran; H₂O / 0.5 h / Ambient temperature

10: 90 percent / CH₂Cl₂ / 6 h / Heating

11: 91 percent / DIBAH / CH₂Cl₂ / 0.75 h / -78 °C

12: 79 percent / imidazole / CH₂Cl₂ / 1 h / Ambient temperature

13: 84 percent / Et₃N, DMAP / toluene / 36 h / 70 °C

14: 90 percent / n-Bu₄F / tetrahydrofuran / 1.5 h / Ambient temperature

15: 1) diethyl (+)-L-tartrate, Ti(OiPr)4, 2) t-BuOOH / 1) CH₂Cl₂, -25 deg C, 7 min, 2) CH₂Cl₂, -20 deg C, overnight

16: CH₂Cl₂ / 0.67 h / Ambient temperature

17: 5percent HClO₄ / acetonitrile / 2.5 h / Ambient temperature

18: 94 percent / EtN(iPr)2 / CH₂Cl₂ / 36 h / Ambient temperature

19: LiAlH₄ / tetrahydrofuran

20: Et₃N, DMAP / CH₂Cl₂

21: 93 percent / EtN(iPr)2 / CH₂Cl₂ / Ambient temperature

22: 100 percent / K₂CO₃ / methanol / 0.67 h / Ambient temperature

23: 94 percent / imidazole / CH₂Cl₂ / 0 - 20 °C

With 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; perchloric acid; diethyl (2R,3R)-tartrate; camphor-10-sulfonic acid; hydrogen; sodium hydride; diisobutylaluminium hydride; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone; toluene; acetonitrile;

DOI:10.1248/cpb.37.1705

Reference yield:

(5S,6R,9R,10S)-9-benzyloxy-9-ethyl-10-(3,4-dimethoxybenzyloxy)-5,6-<1-(4-methoxyphenyl)ethylidenedioxy>-5-methylundec-1-ene (96823-49-3) → (2R,3S,6S)-1-tert-butyldiphenylsilyloxy-6-<(2R,5R,6S)-5-ethyl-5-methoxymethoxy-6-methyltetrahydropyran-2-yl>-3,6-bismethoxymethoxyheptan-2-ol (126394-02-3)

Guidance literature:

Multi-step reaction with 22 steps

1: 81 percent / 1N HCl / tetrahydrofuran / 7.5 h / 45 °C

2: Et₃N / CH₂Cl₂ / 2 h / 0 °C

3: K₂CO₃ / methanol / 0.5 h / Ambient temperature

4: 90 percent / DDQ / H₂O; CH₂Cl₂ / 0.33 h / 0 °C

5: 90 percent / CSA / CH₂Cl₂ / 0.25 h / 0 °C

6: 96 percent / OsO₄, N-methylmorpholine N-oxide / acetone; H₂O / 0.5 h / Ambient temperature

7: hydrogen / Pd/C / ethanol / 72 h / Ambient temperature

8: 96 percent / NaIO₄ / tetrahydrofuran; H₂O / 0.5 h / Ambient temperature

9: 90 percent / CH₂Cl₂ / 6 h / Heating

10: 91 percent / DIBAH / CH₂Cl₂ / 0.75 h / -78 °C

11: 79 percent / imidazole / CH₂Cl₂ / 1 h / Ambient temperature

12: 84 percent / Et₃N, DMAP / toluene / 36 h / 70 °C

13: 90 percent / n-Bu₄F / tetrahydrofuran / 1.5 h / Ambient temperature

14: 1) diethyl (+)-L-tartrate, Ti(OiPr)4, 2) t-BuOOH / 1) CH₂Cl₂, -25 deg C, 7 min, 2) CH₂Cl₂, -20 deg C, overnight

15: CH₂Cl₂ / 0.67 h / Ambient temperature

16: 5percent HClO₄ / acetonitrile / 2.5 h / Ambient temperature

17: 94 percent / EtN(iPr)2 / CH₂Cl₂ / 36 h / Ambient temperature

18: LiAlH₄ / tetrahydrofuran

19: Et₃N, DMAP / CH₂Cl₂

20: 93 percent / EtN(iPr)2 / CH₂Cl₂ / Ambient temperature

21: 100 percent / K₂CO₃ / methanol / 0.67 h / Ambient temperature

22: 94 percent / imidazole / CH₂Cl₂ / 0 - 20 °C

With 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; dmap; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; perchloric acid; diethyl (2R,3R)-tartrate; camphor-10-sulfonic acid; hydrogen; diisobutylaluminium hydride; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetone; toluene; acetonitrile;

DOI:10.1248/cpb.37.1705

upstream raw materials:

(2R,3S,6S)-6-((2R,5R,6S)-5-Ethyl-5-methoxymethoxy-6-methyl-tetrahydro-pyran-2-yl)-3,6-bis-methoxymethoxy-heptane-1,2-diol

tert-butylchlorodiphenylsilane

(2S,3R,6R)-3-ethyl-6-<(2S)-5-hydroxytetrahydrofuran-2-yl>-2-methyltetrahydropyran-3-ol

(2S,3R)-3-Benzyloxy-5-[(4R,5S)-5-but-3-enyl-2-(4-methoxy-phenyl)-2,5-dimethyl-[1,3]dioxolan-4-yl]-3-ethyl-pentan-2-ol

Downstream raw materials:

tert-Butyl-[(2R,3S,6S)-6-((2R,5R,6S)-5-ethyl-5-methoxymethoxy-6-methyl-tetrahydro-pyran-2-yl)-3,6-bis-methoxymethoxy-2-(tetrahydro-pyran-2-yloxy)-heptyloxy]-diphenyl-silane

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