(2S,3S,4R)-2-(tert-butyldimethylsilyloxymethyl)-5-(tert-butyldiphenylsilyloxy)-3-(3,4-dimethoxybenzyloxy)-4-methylpentanal

Base Information

Chemical Name:(2S,3S,4R)-2-(tert-butyldimethylsilyloxymethyl)-5-(tert-butyldiphenylsilyloxy)-3-(3,4-dimethoxybenzyloxy)-4-methylpentanal
CAS No.:240820-99-9
Molecular Formula:C₃₈H₅₆O₆Si₂
Molecular Weight:665.03
Hs Code.:

Synonyms:(2S,3S,4R)-2-(tert-butyldimethylsilyloxymethyl)-5-(tert-butyldiphenylsilyloxy)-3-(3,4-dimethoxybenzyloxy)-4-methylpentanal

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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 (2S,3S,4R)-2-(tert-butyldimethylsilyloxymethyl)-5-(tert-butyldiphenylsilyloxy)-3-(3,4-dimethoxybenzyloxy)-4-methylpentanal

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Technology Process of (2S,3S,4R)-2-(tert-butyldimethylsilyloxymethyl)-5-(tert-butyldiphenylsilyloxy)-3-(3,4-dimethoxybenzyloxy)-4-methylpentanal

There total 17 articles about (2S,3S,4R)-2-(tert-butyldimethylsilyloxymethyl)-5-(tert-butyldiphenylsilyloxy)-3-(3,4-dimethoxybenzyloxy)-4-methylpentanal 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: 98.0%

: 240820-98-8
(2S,3S,4R)-2-(tert-butyldimethylsilyloxymethyl)-5-(tert-butyldiphenylsilyloxy)-3-(3,4-dimethoxybenzyloxy)-4-methylpentan-1-ol

: 240820-99-9
(2S,3S,4R)-2-(tert-butyldimethylsilyloxymethyl)-5-(tert-butyldiphenylsilyloxy)-3-(3,4-dimethoxybenzyloxy)-4-methylpentanal

Guidance literature:: With oxalyl dichloride; iso-PrEtN; dimethyl sulfoxide; In dichloromethane; at -78 - 20 ℃; for 2h;
DOI:10.1248/cpb.47.1288

Reference yield:

: 252006-14-7
3-(tert-butyl-dimethyl-silanyloxymethyl)-6-(tert-butyl-diphenyl-silanyloxy)-4-(3,4-dimethoxy-benzyloxy)-5-methyl-hexane-1,2-diol

: 240820-99-9
(2S,3S,4R)-2-(tert-butyldimethylsilyloxymethyl)-5-(tert-butyldiphenylsilyloxy)-3-(3,4-dimethoxybenzyloxy)-4-methylpentanal

Guidance literature:: With sodium periodate; water; In tetrahydrofuran; Yield given; Ambient temperature;
DOI:10.1055/s-1999-2730

Reference yield:

: 91751-24-5,92817-88-4,123284-89-9,112897-04-8
(R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropanal

: 240820-99-9
(2S,3S,4R)-2-(tert-butyldimethylsilyloxymethyl)-5-(tert-butyldiphenylsilyloxy)-3-(3,4-dimethoxybenzyloxy)-4-methylpentanal

Guidance literature:: Multi-step reaction with 8 steps

1: 70 percent / TiCl₄; iso-Pr₂EtN / CH₂Cl₂ / 3 h / 0 °C

2: LiBH₄ / tetrahydrofuran; diethyl ether / 0.5 h / 0 °C

3: aq. NaOH / diethyl ether

4: 99 percent / dl-camphorsulfonic acid / CH₂Cl₂ / 5 h / 20 °C

5: 93 percent / DIBAH / hexane; toluene / 1 h / -35 °C

6: 99 percent / imidazole / CH₂Cl₂ / 1 h / 0 °C

7: OsO₄; NMO / acetone; H₂O / 3 h / 20 °C

8: NaIO₄ / tetrahydrofuran / 1 h / 20 °C

With 1H-imidazole; sodium hydroxide; sodium periodate; osmium(VIII) oxide; lithium borohydride; N-methyl-2-indolinone; camphor-10-sulfonic acid; titanium tetrachloride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; acetone; toluene; 1: Condensation / 2: Reduction / 3: Hydrolysis / 4: Substitution / 5: reductive ring opening / 6: Condensation / 7: dihydroxylation / 8: oxidative cleavage;
DOI:10.1248/cpb.47.1288