1,1-dimethylethyl N-<(1R,2S,3S)-2-benzoyloxy-3-benzyloxy-4-<(tert-butyldimethylsilyl)oxy>-1-<(trityloxy)methyl>butyl>carbamate

Base Information

Chemical Name:1,1-dimethylethyl N-<(1R,2S,3S)-2-benzoyloxy-3-benzyloxy-4-<(tert-butyldimethylsilyl)oxy>-1-<(trityloxy)methyl>butyl>carbamate
CAS No.:127319-26-0
Molecular Formula:C₄₉H₅₉NO₇Si
Molecular Weight:802.095
Hs Code.:

Synonyms:1,1-dimethylethyl N-<(1R,2S,3S)-2-benzoyloxy-3-benzyloxy-4-<(tert-butyldimethylsilyl)oxy>-1-<(trityloxy)methyl>butyl>carbamate

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Chemical Property of 1,1-dimethylethyl N-<(1R,2S,3S)-2-benzoyloxy-3-benzyloxy-4-<(tert-butyldimethylsilyl)oxy>-1-<(trityloxy)methyl>butyl>carbamate

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Technology Process of 1,1-dimethylethyl N-<(1R,2S,3S)-2-benzoyloxy-3-benzyloxy-4-<(tert-butyldimethylsilyl)oxy>-1-<(trityloxy)methyl>butyl>carbamate

There total 7 articles about 1,1-dimethylethyl N-<(1R,2S,3S)-2-benzoyloxy-3-benzyloxy-4-<(tert-butyldimethylsilyl)oxy>-1-<(trityloxy)methyl>butyl>carbamate 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%

: 127298-77-5,127379-93-5
[(1R,2R,3S)-3-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-1-trityloxymethyl-butyl]-carbamic acid tert-butyl ester

: 65-85-0,8013-63-6
benzoic acid

: 127319-26-0
1,1-dimethylethyl N-<(1R,2S,3S)-2-benzoyloxy-3-benzyloxy-4-<(tert-butyldimethylsilyl)oxy>-1-<(trityloxy)methyl>butyl>carbamate

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; for 14h; Ambient temperature;
DOI:10.1248/cpb.37.3399

Reference yield:

: 100-39-0
benzyl bromide

: 127319-26-0
1,1-dimethylethyl N-<(1R,2S,3S)-2-benzoyloxy-3-benzyloxy-4-<(tert-butyldimethylsilyl)oxy>-1-<(trityloxy)methyl>butyl>carbamate

Guidance literature:: Multi-step reaction with 6 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

With 1H-imidazole; lithium hydroxide; sodium tetrahydroborate; di(n-butyl)tin oxide; triphenylphosphine; cesium fluoride; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; ethanol; N,N-dimethyl-formamide;
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

: 127319-26-0
1,1-dimethylethyl N-<(1R,2S,3S)-2-benzoyloxy-3-benzyloxy-4-<(tert-butyldimethylsilyl)oxy>-1-<(trityloxy)methyl>butyl>carbamate

Guidance literature:: Multi-step reaction with 6 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

With 1H-imidazole; lithium hydroxide; sodium tetrahydroborate; di(n-butyl)tin oxide; triphenylphosphine; cesium fluoride; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; ethanol; N,N-dimethyl-formamide;
DOI:10.1248/cpb.37.3399