(3R,4R,5R)-3-benzyloxy-1-<(tert-butoxy)carbonyl>-4-hydroxy-5-(trityloxy)methyl-2-pyrrolidinone

Base Information

Chemical Name:(3R,4R,5R)-3-benzyloxy-1-<(tert-butoxy)carbonyl>-4-hydroxy-5-(trityloxy)methyl-2-pyrrolidinone
CAS No.:127298-74-2
Molecular Formula:C₃₆H₃₇NO₆
Molecular Weight:579.693
Hs Code.:

Synonyms:

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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 (3R,4R,5R)-3-benzyloxy-1-<(tert-butoxy)carbonyl>-4-hydroxy-5-(trityloxy)methyl-2-pyrrolidinone

Chemical Property:

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Technology Process of (3R,4R,5R)-3-benzyloxy-1-<(tert-butoxy)carbonyl>-4-hydroxy-5-(trityloxy)methyl-2-pyrrolidinone

There total 1 articles about (3R,4R,5R)-3-benzyloxy-1-<(tert-butoxy)carbonyl>-4-hydroxy-5-(trityloxy)methyl-2-pyrrolidinone 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:

: 100-39-0
benzyl bromide

: 127298-73-1
(3R,4R,5R)-3,4-Dihydroxy-2-oxo-5-trityloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

: 127298-74-2
(3R,4R,5R)-3-benzyloxy-1-<(tert-butoxy)carbonyl>-4-hydroxy-5-(trityloxy)methyl-2-pyrrolidinone

Guidance literature:: With di(n-butyl)tin oxide; cesium fluoride; Yield given. Multistep reaction; 1.) toluene, heating, 2 h, 2.) 1 h, over P₂O₅, 3.) DMF, room temperature, 2 h;
DOI:10.1248/cpb.37.3399

Reference yield:

: 127298-74-2
(3R,4R,5R)-3-benzyloxy-1-<(tert-butoxy)carbonyl>-4-hydroxy-5-(trityloxy)methyl-2-pyrrolidinone

: 127298-81-1
[(1R,2S,3S)-4-(tert-Butyl-dimethyl-silanyloxy)-2,3-dihydroxy-1-trityloxymethyl-butyl]-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 2N aqueous LiOH / tetrahydrofuran / 2 h / Ambient temperature

2: diethyl ether

3: 82 percent / NaBH₄ / ethanol / 2 h / Ambient temperature

4: 92 percent / imidazole / dimethylformamide / 5 h / 0 °C

5: 60 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 14 h / Ambient temperature

6: 77 percent / 2N aqueous NaOH / methanol; tetrahydrofuran / 7 h / Ambient temperature

7: 92 percent / hydrogen / palladium black / ethanol / 2 h / Ambient temperature

With 1H-imidazole; lithium hydroxide; sodium hydroxide; sodium tetrahydroborate; hydrogen; triphenylphosphine; diethylazodicarboxylate; palladium; In tetrahydrofuran; methanol; diethyl ether; ethanol; N,N-dimethyl-formamide;
DOI:10.1248/cpb.37.3399

Reference yield:

: 127298-74-2
(3R,4R,5R)-3-benzyloxy-1-<(tert-butoxy)carbonyl>-4-hydroxy-5-(trityloxy)methyl-2-pyrrolidinone

: 126179-24-6
1,1-dimethylethyl N-<(1R,2S,3S)-4-<(aminocarbonyl)oxy>-2,3-<(isopropylidene)dioxy>-1-<(trityloxy)methyl>butyl>carbamate

Guidance literature:: Multi-step reaction with 11 steps

1: 2N aqueous LiOH / tetrahydrofuran / 2 h / Ambient temperature

2: diethyl ether

3: 82 percent / NaBH₄ / ethanol / 2 h / Ambient temperature

4: 92 percent / imidazole / dimethylformamide / 5 h / 0 °C

5: 60 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 14 h / Ambient temperature

6: 77 percent / 2N aqueous NaOH / methanol; tetrahydrofuran / 7 h / Ambient temperature

7: 92 percent / hydrogen / palladium black / ethanol / 2 h / Ambient temperature

8: 87 percent / p-TsOH / acetone / 0.33 h / Ambient temperature

9: 93 percent / tetrabutylammomium fluoride / tetrahydrofuran / 0.08 h / 0 °C

10: pyridine, triethylamine / tetrahydrofuran; diethyl ether / 13 h / 0 °C

11: saturated NH₃ / diethyl ether; methanol / 0.5 h / 0 °C

With pyridine; 1H-imidazole; lithium hydroxide; sodium hydroxide; sodium tetrahydroborate; tetrabutyl ammonium fluoride; ammonia; hydrogen; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium; In tetrahydrofuran; methanol; diethyl ether; ethanol; N,N-dimethyl-formamide; acetone;
DOI:10.1248/cpb.37.3399