(2S,3S,4R)-4-benzylamino-1-O-tert-butyl(diphenyl)silyl-2,3-O-isopropylidene-5-(4-methoxyphenyl)pentan-1,2,3-triol

Base Information

Chemical Name:(2S,3S,4R)-4-benzylamino-1-O-tert-butyl(diphenyl)silyl-2,3-O-isopropylidene-5-(4-methoxyphenyl)pentan-1,2,3-triol
CAS No.:293314-32-6
Molecular Formula:C₃₈H₄₇NO₄Si
Molecular Weight:609.881
Hs Code.:

Synonyms:(2S,3S,4R)-4-benzylamino-1-O-tert-butyl(diphenyl)silyl-2,3-O-isopropylidene-5-(4-methoxyphenyl)pentan-1,2,3-triol

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Chemical Property of (2S,3S,4R)-4-benzylamino-1-O-tert-butyl(diphenyl)silyl-2,3-O-isopropylidene-5-(4-methoxyphenyl)pentan-1,2,3-triol

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Technology Process of (2S,3S,4R)-4-benzylamino-1-O-tert-butyl(diphenyl)silyl-2,3-O-isopropylidene-5-(4-methoxyphenyl)pentan-1,2,3-triol

There total 5 articles about (2S,3S,4R)-4-benzylamino-1-O-tert-butyl(diphenyl)silyl-2,3-O-isopropylidene-5-(4-methoxyphenyl)pentan-1,2,3-triol 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: 60.0%

: 38769-92-5
4-methoxybenzylmagnesium chloride

: 156145-69-6
(4S,5S)-4-cyano-5-<(tert-butyldiphenylsilyl)oxy>methyl-2,2-dimethyl-1,3-dioxolane

: 100-46-9
benzylamine

: 293314-32-6
(2S,3S,4R)-4-benzylamino-1-O-tert-butyl(diphenyl)silyl-2,3-O-isopropylidene-5-(4-methoxyphenyl)pentan-1,2,3-triol

: (2S,3S,4S)-4-benzylamino-1-O-tert-butyl(diphenyl)silyl-2,3-O-isopropylidene-5-(4-methoxyphenyl)pentan-1,2,3-triol

Guidance literature:: 4-methoxybenzylmagnesium chloride; (4S,5S)-4-cyano-5-<(tert-butyldiphenylsilyl)oxy>methyl-2,2-dimethyl-1,3-dioxolane; In tetrahydrofuran; diethyl ether; at 20 ℃; for 4h;

benzylamine; In tetrahydrofuran; methanol; diethyl ether; at 20 ℃; for 0.75h;

With sodium tetrahydroborate; In tetrahydrofuran; methanol; diethyl ether;
DOI:10.1016/S0957-4166(00)00216-0

Reference yield:

: 67844-13-7
methyl (4R,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate

: 293314-32-6
(2S,3S,4R)-4-benzylamino-1-O-tert-butyl(diphenyl)silyl-2,3-O-isopropylidene-5-(4-methoxyphenyl)pentan-1,2,3-triol

Guidance literature:: Multi-step reaction with 4 steps

1.1: Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 15 h

2.1: NH₃ / ethanol / 72 h / 20 °C

3.1: 87 percent / (CF₃CO₂)2O; pyridine / 4 h / 20 °C

4.1: diethyl ether; tetrahydrofuran / 4 h / 20 °C

4.2: diethyl ether; tetrahydrofuran; methanol / 0.75 h / 20 °C

4.3: 60 percent / NaBH₄ / diethyl ether; tetrahydrofuran; methanol

With pyridine; dmap; (CF₃CO₂)2O; ammonia; triethylamine; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; 1.1: Condensation / 2.1: amidation / 3.1: Dehydration / 4.1: metalloimination / 4.2: transimination / 4.3: Reduction;
DOI:10.1016/S0957-4166(00)00216-0

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 293314-32-6
(2S,3S,4R)-4-benzylamino-1-O-tert-butyl(diphenyl)silyl-2,3-O-isopropylidene-5-(4-methoxyphenyl)pentan-1,2,3-triol

Guidance literature:: Multi-step reaction with 4 steps

1.1: Et₃N; 4-dimethylaminopyridine / CH₂Cl₂ / 15 h

2.1: NH₃ / ethanol / 72 h / 20 °C

3.1: 87 percent / (CF₃CO₂)2O; pyridine / 4 h / 20 °C

4.1: diethyl ether; tetrahydrofuran / 4 h / 20 °C

4.2: diethyl ether; tetrahydrofuran; methanol / 0.75 h / 20 °C

4.3: 60 percent / NaBH₄ / diethyl ether; tetrahydrofuran; methanol

With pyridine; dmap; (CF₃CO₂)2O; ammonia; triethylamine; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; 1.1: Condensation / 2.1: amidation / 3.1: Dehydration / 4.1: metalloimination / 4.2: transimination / 4.3: Reduction;
DOI:10.1016/S0957-4166(00)00216-0