[(R)-1-((4S,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-trityloxy-ethyl]-carbamic acid tert-butyl ester

Base Information

Chemical Name:[(R)-1-((4S,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-trityloxy-ethyl]-carbamic acid tert-butyl ester
CAS No.:126199-69-7
Molecular Formula:C₃₂H₃₉NO₆
Molecular Weight:533.665
Hs Code.:

Synonyms:[(R)-1-((4S,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-trityloxy-ethyl]-carbamic acid tert-butyl ester

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Chemical Property of [(R)-1-((4S,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-trityloxy-ethyl]-carbamic acid tert-butyl ester

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Technology Process of [(R)-1-((4S,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-trityloxy-ethyl]-carbamic acid tert-butyl ester

There total 10 articles about [(R)-1-((4S,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-trityloxy-ethyl]-carbamic acid tert-butyl ester 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: 93.0%

: 127319-27-1
1,1-dimethylethyl N-<(1R,2S,3S)-4-<(tert-butyldimethylsilyl)oxy>-2,3-<(isopropylidene)dioxy>-1-<(trityloxy)methyl>butyl>carbamate

: 126199-69-7
[(R)-1-((4S,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-trityloxy-ethyl]-carbamic acid tert-butyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.0833333h;
DOI:10.1248/cpb.37.3399

Reference yield:

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

: 126199-69-7
[(R)-1-((4S,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-trityloxy-ethyl]-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 1.) dibutyltin oxide, 2.) cesium fluoride / 1.) toluene, heating, 2 h, 2.) 1 h, over P₂O₅, 3.) DMF, room temperature, 2 h

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

3: diethyl ether

4: 82 percent / NaBH₄ / ethanol / 2 h / Ambient temperature

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

6: 60 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 14 h / Ambient temperature

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

8: 92 percent / hydrogen / palladium black / ethanol / 2 h / Ambient temperature

9: 87 percent / p-TsOH / acetone / 0.33 h / Ambient temperature

10: 93 percent / tetrabutylammomium fluoride / tetrahydrofuran / 0.08 h / 0 °C

With 1H-imidazole; lithium hydroxide; sodium hydroxide; sodium tetrahydroborate; tetrabutyl ammonium fluoride; hydrogen; di(n-butyl)tin oxide; toluene-4-sulfonic acid; triphenylphosphine; cesium fluoride; diethylazodicarboxylate; palladium; In tetrahydrofuran; methanol; diethyl ether; ethanol; N,N-dimethyl-formamide; acetone;
DOI:10.1248/cpb.37.3399

Reference yield:

: 127298-76-4
1,1-dimethylethyl N-<(1R,2R,3S)-3-benzyloxy-2,4-dihydroxy-1-<(trityloxy)methyl>butyl>carbamate

: 126199-69-7
[(R)-1-((4S,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-trityloxy-ethyl]-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 92 percent / imidazole / dimethylformamide / 5 h / 0 °C

2: 60 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 14 h / Ambient temperature

3: 77 percent / 2N aqueous NaOH / methanol; tetrahydrofuran / 7 h / Ambient temperature

4: 92 percent / hydrogen / palladium black / ethanol / 2 h / Ambient temperature

5: 87 percent / p-TsOH / acetone / 0.33 h / Ambient temperature

6: 93 percent / tetrabutylammomium fluoride / tetrahydrofuran / 0.08 h / 0 °C

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