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

Base Information

• Chemical Name: 1,1-dimethylethyl N-<(1R,2S,3S)-4-<(tert-butyldimethylsilyl)oxy>-2,3-<(isopropylidene)dioxy>-1-<(trityloxy)methyl>butyl>carbamate
• CAS No.: 127319-27-1
• Molecular Formula: C₃₈H₅₃NO₆Si
• Molecular Weight: 647.927

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about 1,1-dimethylethyl N-<(1R,2S,3S)-4-<(tert-butyldimethylsilyl)oxy>-2,3-<(isopropylidene)dioxy>-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: 87.0%

[(1R,2S,3S)-4-(tert-Butyl-dimethyl-silanyloxy)-2,3-dihydroxy-1-trityloxymethyl-butyl]-carbamic acid tert-butyl ester (127298-81-1) + 2,2-dimethoxy-propane (77-76-9) → 1,1-dimethylethyl N-<(1R,2S,3S)-4-<(tert-butyldimethylsilyl)oxy>-2,3-<(isopropylidene)dioxy>-1-<(trityloxy)methyl>butyl>carbamate (127319-27-1)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; for 0.333333h; Ambient temperature;

DOI:10.1248/cpb.37.3399

Reference yield:

(3R,4R,5R)-3,4-Dihydroxy-2-oxo-5-trityloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (127298-73-1) → 1,1-dimethylethyl N-<(1R,2S,3S)-4-<(tert-butyldimethylsilyl)oxy>-2,3-<(isopropylidene)dioxy>-1-<(trityloxy)methyl>butyl>carbamate (127319-27-1)

Guidance literature:

Multi-step reaction with 9 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

With 1H-imidazole; lithium hydroxide; sodium hydroxide; sodium tetrahydroborate; 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:

1,1-dimethylethyl N-<(1R,2R,3S)-3-benzyloxy-2,4-dihydroxy-1-<(trityloxy)methyl>butyl>carbamate (127298-76-4) → 1,1-dimethylethyl N-<(1R,2S,3S)-4-<(tert-butyldimethylsilyl)oxy>-2,3-<(isopropylidene)dioxy>-1-<(trityloxy)methyl>butyl>carbamate (127319-27-1)

Guidance literature:

Multi-step reaction with 5 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

With 1H-imidazole; sodium hydroxide; hydrogen; toluene-4-sulfonic acid; triphenylphosphine; diethylazodicarboxylate; palladium; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide; acetone;

DOI:10.1248/cpb.37.3399

upstream raw materials:

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

2,2-dimethoxy-propane

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

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

Downstream raw materials:

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

[(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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