(4R)-2-[(1'R,2'S)-1',2'-Methano-3'-(tert-butyldiphenylsilyloxy)propyl]-4-hydroxymethyl-4,5-dihydrothiazole

Base Information

Chemical Name:(4R)-2-[(1'R,2'S)-1',2'-Methano-3'-(tert-butyldiphenylsilyloxy)propyl]-4-hydroxymethyl-4,5-dihydrothiazole
CAS No.:251444-01-6
Molecular Formula:C₂₄H₃₁NO₂SSi
Molecular Weight:425.667
Hs Code.:

Synonyms:(4R)-2-[(1'R,2'S)-1',2'-Methano-3'-(tert-butyldiphenylsilyloxy)propyl]-4-hydroxymethyl-4,5-dihydrothiazole

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Chemical Property of (4R)-2-[(1'R,2'S)-1',2'-Methano-3'-(tert-butyldiphenylsilyloxy)propyl]-4-hydroxymethyl-4,5-dihydrothiazole

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Technology Process of (4R)-2-[(1'R,2'S)-1',2'-Methano-3'-(tert-butyldiphenylsilyloxy)propyl]-4-hydroxymethyl-4,5-dihydrothiazole

There total 8 articles about (4R)-2-[(1'R,2'S)-1',2'-Methano-3'-(tert-butyldiphenylsilyloxy)propyl]-4-hydroxymethyl-4,5-dihydrothiazole 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: 82.0%

: 251444-07-2
(4R)-2-[(1'R,2'S)-1',2'-Methano-3'-(tert-butyldiphenylsilyloxy)propyl]-4-methoxycarbonyl-4,5-dihydrothiazole

: 251444-01-6
(4R)-2-[(1'R,2'S)-1',2'-Methano-3'-(tert-butyldiphenylsilyloxy)propyl]-4-hydroxymethyl-4,5-dihydrothiazole

Guidance literature:: With diethylamine; In tetrahydrofuran; for 0.0833333h;
DOI:10.1039/a904378k

Reference yield:

: 154001-53-3
(1Z,4'S)-3-<(tert-Butyldiphenylsilyl)oxy>-1-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)-1-propene

: 251444-01-6
(4R)-2-[(1'R,2'S)-1',2'-Methano-3'-(tert-butyldiphenylsilyloxy)propyl]-4-hydroxymethyl-4,5-dihydrothiazole

Guidance literature:: Multi-step reaction with 7 steps

1: 97 percent / Et₂Zn / hexane; CH₂Cl₂ / -23 - 0 °C

2: 100 percent / H₅IO₆ / diethyl ether / 10 h / 20 °C

3: 97 percent / KMnO₄; potassium hydrogen orthophosphate buffer; H₂O / 2-methyl-propan-2-ol / 0.08 h / pH 4.4

4: N-methylmorpholine / CH₂Cl₂ / 0.25 h / -10 °C

5: N-methylmorpholine / CH₂Cl₂ / 2 h / 20 °C

6: 91 percent / TiCl₄ / CH₂Cl₂ / 2 h / 0 °C

7: 82 percent / Et₂NH / tetrahydrofuran / 0.08 h

With 4-methyl-morpholine; potassium permanganate; potassium hydrogen orthophosphate buffer; water; diethylzinc; titanium tetrachloride; periodic acid; diethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; tert-butyl alcohol; 1: Addition / 2: Oxidation / 3: Oxidation / 4: Substitution / 5: Acylation / 6: Cyclization / 7: Reduction;
DOI:10.1039/a904378k

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 251444-01-6
(4R)-2-[(1'R,2'S)-1',2'-Methano-3'-(tert-butyldiphenylsilyloxy)propyl]-4-hydroxymethyl-4,5-dihydrothiazole

Guidance literature:: Multi-step reaction with 8 steps

1: 93 percent / Et₃N; DMAP / CH₂Cl₂

2: 97 percent / Et₂Zn / hexane; CH₂Cl₂ / -23 - 0 °C

3: 100 percent / H₅IO₆ / diethyl ether / 10 h / 20 °C

4: 97 percent / KMnO₄; potassium hydrogen orthophosphate buffer; H₂O / 2-methyl-propan-2-ol / 0.08 h / pH 4.4

5: N-methylmorpholine / CH₂Cl₂ / 0.25 h / -10 °C

6: N-methylmorpholine / CH₂Cl₂ / 2 h / 20 °C

7: 91 percent / TiCl₄ / CH₂Cl₂ / 2 h / 0 °C

8: 82 percent / Et₂NH / tetrahydrofuran / 0.08 h

With 4-methyl-morpholine; dmap; potassium permanganate; potassium hydrogen orthophosphate buffer; water; diethylzinc; titanium tetrachloride; periodic acid; diethylamine; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; tert-butyl alcohol; 1: Etherification / 2: Addition / 3: Oxidation / 4: Oxidation / 5: Substitution / 6: Acylation / 7: Cyclization / 8: Reduction;
DOI:10.1039/a904378k