(2S,3S,5R)-3-(tert-Butyldimethylsiloxy)-9-(tert-butyldiphenylsiloxy)-5-(4-methoxybenzyloxy)-2-methylnonanal

Base Information

Chemical Name:(2S,3S,5R)-3-(tert-Butyldimethylsiloxy)-9-(tert-butyldiphenylsiloxy)-5-(4-methoxybenzyloxy)-2-methylnonanal
CAS No.:529510-42-7
Molecular Formula:C₄₀H₆₀O₅Si₂
Molecular Weight:677.084
Hs Code.:

Synonyms:(2S,3S,5R)-3-(tert-Butyldimethylsiloxy)-9-(tert-butyldiphenylsiloxy)-5-(4-methoxybenzyloxy)-2-methylnonanal

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Chemical Property of (2S,3S,5R)-3-(tert-Butyldimethylsiloxy)-9-(tert-butyldiphenylsiloxy)-5-(4-methoxybenzyloxy)-2-methylnonanal

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Technology Process of (2S,3S,5R)-3-(tert-Butyldimethylsiloxy)-9-(tert-butyldiphenylsiloxy)-5-(4-methoxybenzyloxy)-2-methylnonanal

There total 11 articles about (2S,3S,5R)-3-(tert-Butyldimethylsiloxy)-9-(tert-butyldiphenylsiloxy)-5-(4-methoxybenzyloxy)-2-methylnonanal 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: 86.0%

: 1052661-41-2
3-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2-methyl-nonan-1-ol

: 529510-42-7
(2S,3S,5R)-3-(tert-Butyldimethylsiloxy)-9-(tert-butyldiphenylsiloxy)-5-(4-methoxybenzyloxy)-2-methylnonanal

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 0 ℃; for 4h; Inert atmosphere;
DOI:10.1021/ol801493w

Reference yield: 37.0%

: 529510-41-6
tert-butyl (2S,3S,5R)-3-(tert-butyldimethylsiloxy)-9-(tert-butyldiphenylsiloxy)-5-(4-methoxybenzyloxy)-2-methylnonanoate

: 529510-42-7
(2S,3S,5R)-3-(tert-Butyldimethylsiloxy)-9-(tert-butyldiphenylsiloxy)-5-(4-methoxybenzyloxy)-2-methylnonanal

: 1052661-41-2
3-(tert-butyl-dimethyl-silanyloxy)-9-(tert-butyl-diphenyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2-methyl-nonan-1-ol

Guidance literature:: With diisobutylaluminium hydride; In toluene; at -78 ℃; for 4h; Inert atmosphere;
DOI:10.1021/ol801493w

Reference yield:

: 542-28-9,26354-94-9
3,4,5,6-tetrahydro-2H-pyran-2-one

: 529510-42-7
(2S,3S,5R)-3-(tert-Butyldimethylsiloxy)-9-(tert-butyldiphenylsiloxy)-5-(4-methoxybenzyloxy)-2-methylnonanal

Guidance literature:: Multi-step reaction with 10 steps

1: 74 percent / LDA / tetrahydrofuran / 2 h / -78 °C

2: 86 percent / (R)-MeO-BIPHEP; RuCl₃; H₂ / ethanol / 25 h / 80 °C / 7500.6 Torr

3: 98 percent / NEt₃; 4-DMAP / CH₂Cl₂ / 20 h / 20 °C

4: 82 percent / CSA / CH₂Cl₂ / 20 °C

5: 91 percent / LDA / tetrahydrofuran / 5 h / -65 - -30 °C

6: 80 percent / H₂ / (S)-(MeO-BIPHEP)RuBr₃ / 2-methyl-propan-2-ol; CH₂Cl₂ / 68 h / 50 °C / 75006 Torr

7: 74 percent / LDA; HMPA / tetrahydrofuran / 3.5 h / -55 - 20 °C

8: 97 percent / 2,6-lutidine / CH₂Cl₂ / -20 °C

9: DIBAL / toluene / 3.5 h / -78 °C

10: Dess-Martin periodinane / CH₂Cl₂ / 4 h / 0 - 20 °C

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; ruthenium trichloride; hydrogen; diisobutylaluminium hydride; Dess-Martin periodane; (R)-(6,6′-dimethoxy-[1,1′-biphenyl]-2,2′-diyl)bis(diphenylphosphine); triethylamine; lithium diisopropyl amide; camphor-10-sulfonic acid; (S)-(-)-(6,6’-dimethoxybiphenyl-2,2’-diyl)bis(diphenylphosphine); In tetrahydrofuran; ethanol; dichloromethane; toluene; tert-butyl alcohol; 10: Dess-Martin oxidation;
DOI:10.1016/S0040-4039(03)00110-2