(3R,4S)-4-Benzo[1,3]dioxol-5-yl-3-(tert-butyl-diphenyl-silanyloxymethyl)-4-methoxymethoxy-butyraldehyde

Base Information

Chemical Name:(3R,4S)-4-Benzo[1,3]dioxol-5-yl-3-(tert-butyl-diphenyl-silanyloxymethyl)-4-methoxymethoxy-butyraldehyde
CAS No.:195321-36-9
Molecular Formula:C₃₀H₃₆O₆Si
Molecular Weight:520.698
Hs Code.:

Synonyms:(3R,4S)-4-Benzo[1,3]dioxol-5-yl-3-(tert-butyl-diphenyl-silanyloxymethyl)-4-methoxymethoxy-butyraldehyde

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Chemical Property of (3R,4S)-4-Benzo[1,3]dioxol-5-yl-3-(tert-butyl-diphenyl-silanyloxymethyl)-4-methoxymethoxy-butyraldehyde

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Technology Process of (3R,4S)-4-Benzo[1,3]dioxol-5-yl-3-(tert-butyl-diphenyl-silanyloxymethyl)-4-methoxymethoxy-butyraldehyde

There total 7 articles about (3R,4S)-4-Benzo[1,3]dioxol-5-yl-3-(tert-butyl-diphenyl-silanyloxymethyl)-4-methoxymethoxy-butyraldehyde 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%

: 195321-35-8
(4R,5S)-5-Benzo[1,3]dioxol-5-yl-4-(tert-butyl-diphenyl-silanyloxymethyl)-5-methoxymethoxy-pentane-1,2-diol

: 195321-36-9
(3R,4S)-4-Benzo[1,3]dioxol-5-yl-3-(tert-butyl-diphenyl-silanyloxymethyl)-4-methoxymethoxy-butyraldehyde

Guidance literature:: With sodium periodate; In tetrahydrofuran; water; at 0 ℃; for 6.5h;
DOI:10.1021/jo971027c

Reference yield:

: 120-57-0,30024-74-9
piperonal

: 195321-36-9
(3R,4S)-4-Benzo[1,3]dioxol-5-yl-3-(tert-butyl-diphenyl-silanyloxymethyl)-4-methoxymethoxy-butyraldehyde

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) dibutylboron triflate, 2.) Et₃N / 1) CH₂Cl₂, 0 deg C; 2) CH₂Cl₂, 0 deg C, 10 min; 3) CH₂Cl₂, -78 deg C, 30 min, 0 deg C, 1 h

2: 82 percent / LiBH₄ / H₂O; diethyl ether; tetrahydrofuran / 1.25 h / 0 °C

3: 87 percent / imidazole / tetrahydrofuran / 5.25 h / Ambient temperature

4: 98 percent / diisopropylethylamine / CH₂Cl₂ / 21 h / Ambient temperature

5: 97 percent / N-methylmorpholine N-oxide, OsO₄ / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 5.5 h / Ambient temperature

6: 86 percent / NaIO₄ / tetrahydrofuran; H₂O / 6.5 h / 0 °C

With 1H-imidazole; sodium periodate; osmium(VIII) oxide; lithium borohydride; di-n-butylboryl trifluoromethanesulfonate; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/jo971027c

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 195321-36-9
(3R,4S)-4-Benzo[1,3]dioxol-5-yl-3-(tert-butyl-diphenyl-silanyloxymethyl)-4-methoxymethoxy-butyraldehyde

Guidance literature:: Multi-step reaction with 4 steps

1: 87 percent / imidazole / tetrahydrofuran / 5.25 h / Ambient temperature

2: 98 percent / diisopropylethylamine / CH₂Cl₂ / 21 h / Ambient temperature

3: 97 percent / N-methylmorpholine N-oxide, OsO₄ / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 5.5 h / Ambient temperature

4: 86 percent / NaIO₄ / tetrahydrofuran; H₂O / 6.5 h / 0 °C

With 1H-imidazole; sodium periodate; osmium(VIII) oxide; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/jo971027c