(2R,3R,4S)-N-tert-butyloxycarbonyl-4-benzoyloxy-3-hydroxy-2-(tert-butyldiphenylsiloxymethyl)pyrrolidine

Base Information

Chemical Name:(2R,3R,4S)-N-tert-butyloxycarbonyl-4-benzoyloxy-3-hydroxy-2-(tert-butyldiphenylsiloxymethyl)pyrrolidine
CAS No.:852616-69-4
Molecular Formula:C₃₃H₄₁NO₆Si
Molecular Weight:575.777
Hs Code.:

Synonyms:(2R,3R,4S)-N-tert-butyloxycarbonyl-4-benzoyloxy-3-hydroxy-2-(tert-butyldiphenylsiloxymethyl)pyrrolidine

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Chemical Property of (2R,3R,4S)-N-tert-butyloxycarbonyl-4-benzoyloxy-3-hydroxy-2-(tert-butyldiphenylsiloxymethyl)pyrrolidine

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Technology Process of (2R,3R,4S)-N-tert-butyloxycarbonyl-4-benzoyloxy-3-hydroxy-2-(tert-butyldiphenylsiloxymethyl)pyrrolidine

There total 9 articles about (2R,3R,4S)-N-tert-butyloxycarbonyl-4-benzoyloxy-3-hydroxy-2-(tert-butyldiphenylsiloxymethyl)pyrrolidine 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: 70.0%

: 852616-66-1
tert-butyl (2R,3R,4S)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-3,4-dihydroxypyrrolidine-1-carboxylate

: 98-88-4
benzoyl chloride

: 852616-69-4
(2R,3R,4S)-N-tert-butyloxycarbonyl-4-benzoyloxy-3-hydroxy-2-(tert-butyldiphenylsiloxymethyl)pyrrolidine

: (2R,3R,4S)-N-tert-butyloxycarbonyl-3-benzoyloxy-4-hydroxy-2-(tert-butyldiphenylsiloxymethyl)pyrrolidine

Guidance literature:: With pyridine; dmap; In dichloromethane; at -78 - -10 ℃;
DOI:10.1021/jo050057+

Reference yield:

: 852616-64-9
tert-butyl (S)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,5-dihydro-1H-pyrrole-1-carboxylate

: 852616-69-4
(2R,3R,4S)-N-tert-butyloxycarbonyl-4-benzoyloxy-3-hydroxy-2-(tert-butyldiphenylsiloxymethyl)pyrrolidine

Guidance literature:: Multi-step reaction with 2 steps

1: 92 percent / OsO₄; 4-methylmorpholine N-oxide monohydrate / acetone; H₂O; toluene / 0 - 20 °C

2: 70 percent / DMAP; pyridine / CH₂Cl₂ / -78 - -10 °C

With pyridine; dmap; osmium(VIII) oxide; 4-methylmorpholine 4-oxide monohydrate; In dichloromethane; water; acetone; toluene;
DOI:10.1021/jo050057+

Reference yield:

: 1499-56-5,775275-31-5,790644-51-8,754962-86-2
(R)-4-hydroxy-L-proline ethyl ester

: 852616-69-4
(2R,3R,4S)-N-tert-butyloxycarbonyl-4-benzoyloxy-3-hydroxy-2-(tert-butyldiphenylsiloxymethyl)pyrrolidine

Guidance literature:: Multi-step reaction with 7 steps

1.1: 15.529 g / DMAP; Et₃N / CH₂Cl₂ / Cooling

2.1: 78 percent / DMAP; Et₃N / CH₂Cl₂ / 2 h / 0 °C

3.1: PhSeSePh; NaBH₄ / methanol / 11 h / Heating

3.2: 63 percent / pyridine; H₂O₂ / CH₂Cl₂; H₂O / 2 h / 20 °C

4.1: 89 percent / LiAlH₄ / diethyl ether / 0 - 20 °C

5.1: 82 percent / imidazole; DMAP / CH₂Cl₂ / 0 - 20 °C

6.1: 92 percent / OsO₄; 4-methylmorpholine N-oxide monohydrate / acetone; H₂O; toluene / 0 - 20 °C

7.1: 70 percent / DMAP; pyridine / CH₂Cl₂ / -78 - -10 °C

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; osmium(VIII) oxide; lithium aluminium tetrahydride; diphenyl diselenide; 4-methylmorpholine 4-oxide monohydrate; triethylamine; In methanol; diethyl ether; dichloromethane; water; acetone; toluene;
DOI:10.1021/jo050057+