(2R,3S)-3-[N-allyloxycarbonyl-3-benzyloxy-5-benzyloxymethoxymethyl-2-(2-hydroxyethyl)anilino]methyl-1-p-toluenesulfonyl-2-aziridinemethanol

Base Information

Chemical Name:(2R,3S)-3-[N-allyloxycarbonyl-3-benzyloxy-5-benzyloxymethoxymethyl-2-(2-hydroxyethyl)anilino]methyl-1-p-toluenesulfonyl-2-aziridinemethanol
CAS No.:177958-00-8
Molecular Formula:C₃₉H₄₄N₂O₉S
Molecular Weight:716.852
Hs Code.:

(2R,3S)-3-[N-allyloxycarbonyl-3-benzyloxy-5-benzyloxymethoxymethyl-2-(2-hydroxyethyl)anilino]methyl-1-p-toluenesulfonyl-2-aziridinemethanol

Synonyms:(2R,3S)-3-[N-allyloxycarbonyl-3-benzyloxy-5-benzyloxymethoxymethyl-2-(2-hydroxyethyl)anilino]methyl-1-p-toluenesulfonyl-2-aziridinemethanol

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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 (2R,3S)-3-[N-allyloxycarbonyl-3-benzyloxy-5-benzyloxymethoxymethyl-2-(2-hydroxyethyl)anilino]methyl-1-p-toluenesulfonyl-2-aziridinemethanol

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (2R,3S)-3-[N-allyloxycarbonyl-3-benzyloxy-5-benzyloxymethoxymethyl-2-(2-hydroxyethyl)anilino]methyl-1-p-toluenesulfonyl-2-aziridinemethanol

There total 8 articles about (2R,3S)-3-[N-allyloxycarbonyl-3-benzyloxy-5-benzyloxymethoxymethyl-2-(2-hydroxyethyl)anilino]methyl-1-p-toluenesulfonyl-2-aziridinemethanol 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: 99.0%

: 177957-99-2
{3-Benzyloxy-5-benzyloxymethoxymethyl-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-phenyl}-[(2S,3S)-3-(tert-butyl-diphenyl-silanyloxymethyl)-1-(toluene-4-sulfonyl)-aziridin-2-ylmethyl]-carbamic acid allyl ester

: 177958-00-8
(2R,3S)-3-[N-allyloxycarbonyl-3-benzyloxy-5-benzyloxymethoxymethyl-2-(2-hydroxyethyl)anilino]methyl-1-p-toluenesulfonyl-2-aziridinemethanol

Guidance literature:: With pyridine hydrogenfluoride; In pyridine; at 0 ℃;
DOI:10.1016/0040-4039(96)00595-3

Reference yield:

: 98-59-9
p-toluenesulfonyl chloride

: 177958-00-8
(2R,3S)-3-[N-allyloxycarbonyl-3-benzyloxy-5-benzyloxymethoxymethyl-2-(2-hydroxyethyl)anilino]methyl-1-p-toluenesulfonyl-2-aziridinemethanol

Guidance literature:: Multi-step reaction with 4 steps

1: Et₃N / dimethylformamide / 4 h / Ambient temperature

2: 94 percent / Et₃N / CH₂Cl₂ / 3 h / Ambient temperature

3: 92 percent / NaH, imidazole / paraffin; tetrahydrofuran / 0.5 h / Heating

4: 99 percent / (HF)n*Py / 0.67 h / -10 °C

With 1H-imidazole; (HF)n*Py; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; paraffin;
DOI:10.1016/S0040-4020(97)00652-2

Reference yield:

: 177957-70-9
{3-Benzyloxy-5-benzyloxymethoxymethyl-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-phenyl}-carbamic acid allyl ester

: 177958-00-8
(2R,3S)-3-[N-allyloxycarbonyl-3-benzyloxy-5-benzyloxymethoxymethyl-2-(2-hydroxyethyl)anilino]methyl-1-p-toluenesulfonyl-2-aziridinemethanol

Guidance literature:: Multi-step reaction with 6 steps

1: 100 percent / NaH / paraffin; tetrahydrofuran / 1.) -78 deg C -> room temperature, 4 h, 2.) room temperature, 2 h

2: 16.1 g / Zn, AcOH / tetrahydrofuran; H₂O / 1 h / Ambient temperature

3: Et₃N / dimethylformamide / 4 h / Ambient temperature

4: 94 percent / Et₃N / CH₂Cl₂ / 3 h / Ambient temperature

5: 92 percent / NaH, imidazole / paraffin; tetrahydrofuran / 0.5 h / Heating

6: 99 percent / (HF)n*Py / 0.67 h / -10 °C

With 1H-imidazole; (HF)n*Py; sodium hydride; acetic acid; triethylamine; zinc; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; paraffin;
DOI:10.1016/S0040-4020(97)00652-2