(4R,5S,6S)-9-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2,2,4,6-tetramethylnonanal

Base Information

Chemical Name:(4R,5S,6S)-9-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2,2,4,6-tetramethylnonanal
CAS No.:851955-75-4
Molecular Formula:C₂₆H₄₄O₄Si
Molecular Weight:448.718
Hs Code.:

Synonyms:

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (4R,5S,6S)-9-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2,2,4,6-tetramethylnonanal

Chemical Property:

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Technology Process of (4R,5S,6S)-9-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2,2,4,6-tetramethylnonanal

There total 11 articles about (4R,5S,6S)-9-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2,2,4,6-tetramethylnonanal 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:

: (5R,6S,7S)-10-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-1,2-dihydroxy-3,3,5,7-tetramethyl-decan-4-one

: 851955-75-4
(4R,5S,6S)-9-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2,2,4,6-tetramethylnonanal

Guidance literature:: With sodium periodate; In tetrahydrofuran; water; at 20 ℃; for 6h;
DOI:10.1016/j.bioorg.2004.11.002

Reference yield:

: 851955-71-0
(2R,3S,4S)-7-Benzyloxy-3-hydroxy-2,4-dimethyl-heptanoic acid methoxy-methyl-amide

: 851955-75-4
(4R,5S,6S)-9-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2,2,4,6-tetramethylnonanal

Guidance literature:: Multi-step reaction with 6 steps

1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

2: 91 percent / DIBALH / tetrahydrofuran; toluene / 1 h / -78 - -50 °C

3: 94 percent / tetrahydrofuran / 1 h / 20 °C

4: 76 percent / 4-methylmorpholine 4-oxide; tetrapropylammonium perruthenate / CH₂Cl₂; acetonitrile / 2 h / 20 °C

5: 4-methylmorpholine 4-oxide; OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 16 h / 20 °C

6: 6.29 g / NaIO₄ / tetrahydrofuran; H₂O / 6 h / 20 °C

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; tetrapropylammonium perruthennate; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane; water; toluene; acetonitrile; tert-butyl alcohol;
DOI:10.1016/j.bioorg.2004.11.002

Reference yield:

: 851955-69-6
5-(benzyloxy)-N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylpentanamide

: 851955-75-4
(4R,5S,6S)-9-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-2,2,4,6-tetramethylnonanal

Guidance literature:: Multi-step reaction with 10 steps

1.1: 94 percent / LiCl; iPr₂NH; BuLi / tetrahydrofuran; hexane / 0.75 h / 0 °C

2.1: 75 percent / iPr₂NH; BuLi; BH₃*NH₃ / hexane; tetrahydrofuran / 16 h / 20 °C

3.1: 84 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1.17 h / -78 - -30 °C

4.1: Bu₂B-OTf; Et₃N / CH₂Cl₂ / 2.5 h / -78 - 0 °C

4.2: 8 g / Me₃Al / tetrahydrofuran; hexane / 16 h / -5 - 20 °C

5.1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

6.1: 91 percent / DIBALH / tetrahydrofuran; toluene / 1 h / -78 - -50 °C

7.1: 94 percent / tetrahydrofuran / 1 h / 20 °C

8.1: 76 percent / 4-methylmorpholine 4-oxide; tetrapropylammonium perruthenate / CH₂Cl₂; acetonitrile / 2 h / 20 °C

9.1: 4-methylmorpholine 4-oxide; OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 16 h / 20 °C

10.1: 6.29 g / NaIO₄ / tetrahydrofuran; H₂O / 6 h / 20 °C

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; n-butyllithium; borane-ammonia complex; tetrapropylammonium perruthennate; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; diisopropylamine; lithium chloride; In tetrahydrofuran; hexane; dichloromethane; water; toluene; acetonitrile; tert-butyl alcohol; 3.1: Swern oxidation;
DOI:10.1016/j.bioorg.2004.11.002