(2S,4R,6R,7R,8R,9S)-2,4,6-tris(tert-butyldimethylsilyloxy)-8-(4-methoxybenzyloxy)-7,9-dimethyl-10-(triethylsilyloxy)decanal

Base Information

Chemical Name:(2S,4R,6R,7R,8R,9S)-2,4,6-tris(tert-butyldimethylsilyloxy)-8-(4-methoxybenzyloxy)-7,9-dimethyl-10-(triethylsilyloxy)decanal
CAS No.:929882-85-9
Molecular Formula:C₄₄H₈₈O₇Si₄
Molecular Weight:841.521
Hs Code.:

Synonyms:(2S,4R,6R,7R,8R,9S)-2,4,6-tris(tert-butyldimethylsilyloxy)-8-(4-methoxybenzyloxy)-7,9-dimethyl-10-(triethylsilyloxy)decanal

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Chemical Property of (2S,4R,6R,7R,8R,9S)-2,4,6-tris(tert-butyldimethylsilyloxy)-8-(4-methoxybenzyloxy)-7,9-dimethyl-10-(triethylsilyloxy)decanal

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Technology Process of (2S,4R,6R,7R,8R,9S)-2,4,6-tris(tert-butyldimethylsilyloxy)-8-(4-methoxybenzyloxy)-7,9-dimethyl-10-(triethylsilyloxy)decanal

There total 4 articles about (2S,4R,6R,7R,8R,9S)-2,4,6-tris(tert-butyldimethylsilyloxy)-8-(4-methoxybenzyloxy)-7,9-dimethyl-10-(triethylsilyloxy)decanal 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: 85.0%

: 929883-07-8
(2S,4R,6R,7R,8R,9S)-2,4,6-tris(tert-butyldimethylsilyloxy)-8-(4-methoxybenzyloxy)-7,9-dimethyl-10-(triethylsilyloxy)decan-1-ol

: 929882-85-9
(2S,4R,6R,7R,8R,9S)-2,4,6-tris(tert-butyldimethylsilyloxy)-8-(4-methoxybenzyloxy)-7,9-dimethyl-10-(triethylsilyloxy)decanal

Guidance literature:: With pyridine; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1.5h;
DOI:10.1002/anie.200603654

Reference yield:

: 929882-83-7
(R)-3-((2R,3S,4S,5R,7R,9S)-10-(benzyloxy)-7,9-bis(tert-butyldimethylsilyloxy)-3,5-dihydroxy-2,4-dimethyldecanoyl)-4-benzyloxazolidin-2-one

: 929882-85-9
(2S,4R,6R,7R,8R,9S)-2,4,6-tris(tert-butyldimethylsilyloxy)-8-(4-methoxybenzyloxy)-7,9-dimethyl-10-(triethylsilyloxy)decanal

Guidance literature:: Multi-step reaction with 7 steps

1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -5 °C

2: lithium borohydride / diethyl ether; H₂O / 1 h / 0 °C

3: 94 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 14 h / 20 °C

4: 91 percent / BH₃*THF; Sc(OTf)3 / CH₂Cl₂; tetrahydrofuran / 1 h

5: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0.42 h

6: 88 percent / hydrogen / Pd(OH)2/C / ethyl acetate / 1.83 h / 20 °C / atmospheric pressure

7: 85 percent / pyridine; Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

With pyridine; 2,6-dimethylpyridine; lithium borohydride; borane-THF; hydrogen; pyridinium p-toluenesulfonate; Dess-Martin periodane; scandium tris(trifluoromethanesulfonate); palladium dihydroxide; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate;
DOI:10.1002/anie.200603654

Reference yield:

: 929882-93-9
(R)-3-((2R,3S,4R,5R,7R,9S)-10-(benzyloxy)-5,7,9-tris(tert-butyldimethylsilyloxy)-3-hydroxy-2,4-dimethyldecanoyl)-4-benzyloxazolidin-2-one

: 929882-85-9
(2S,4R,6R,7R,8R,9S)-2,4,6-tris(tert-butyldimethylsilyloxy)-8-(4-methoxybenzyloxy)-7,9-dimethyl-10-(triethylsilyloxy)decanal

Guidance literature:: Multi-step reaction with 6 steps

1: lithium borohydride / diethyl ether; H₂O / 1 h / 0 °C

2: 94 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 14 h / 20 °C

3: 91 percent / BH₃*THF; Sc(OTf)3 / CH₂Cl₂; tetrahydrofuran / 1 h

4: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0.42 h

5: 88 percent / hydrogen / Pd(OH)2/C / ethyl acetate / 1.83 h / 20 °C / atmospheric pressure

6: 85 percent / pyridine; Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

With pyridine; 2,6-dimethylpyridine; lithium borohydride; borane-THF; hydrogen; pyridinium p-toluenesulfonate; Dess-Martin periodane; scandium tris(trifluoromethanesulfonate); palladium dihydroxide; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate;
DOI:10.1002/anie.200603654