[3-Benzyloxy-5-benzyloxymethoxymethyl-2-(2-oxo-ethyl)-phenyl]-[(2S,3S)-3-formyl-1-(toluene-4-sulfonyl)-aziridin-2-ylmethyl]-carbamic acid allyl ester

Base Information

Chemical Name:[3-Benzyloxy-5-benzyloxymethoxymethyl-2-(2-oxo-ethyl)-phenyl]-[(2S,3S)-3-formyl-1-(toluene-4-sulfonyl)-aziridin-2-ylmethyl]-carbamic acid allyl ester
CAS No.:177958-01-9
Molecular Formula:C₃₉H₄₀N₂O₉S
Molecular Weight:712.821
Hs Code.:

[3-Benzyloxy-5-benzyloxymethoxymethyl-2-(2-oxo-ethyl)-phenyl]-[(2S,3S)-3-formyl-1-(toluene-4-sulfonyl)-aziridin-2-ylmethyl]-carbamic acid allyl ester

Synonyms:[3-Benzyloxy-5-benzyloxymethoxymethyl-2-(2-oxo-ethyl)-phenyl]-[(2S,3S)-3-formyl-1-(toluene-4-sulfonyl)-aziridin-2-ylmethyl]-carbamic acid allyl ester

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Chemical Property of [3-Benzyloxy-5-benzyloxymethoxymethyl-2-(2-oxo-ethyl)-phenyl]-[(2S,3S)-3-formyl-1-(toluene-4-sulfonyl)-aziridin-2-ylmethyl]-carbamic acid allyl ester

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Technology Process of [3-Benzyloxy-5-benzyloxymethoxymethyl-2-(2-oxo-ethyl)-phenyl]-[(2S,3S)-3-formyl-1-(toluene-4-sulfonyl)-aziridin-2-ylmethyl]-carbamic acid allyl ester

There total 8 articles about [3-Benzyloxy-5-benzyloxymethoxymethyl-2-(2-oxo-ethyl)-phenyl]-[(2S,3S)-3-formyl-1-(toluene-4-sulfonyl)-aziridin-2-ylmethyl]-carbamic acid allyl 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: 98.0%

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

: 177958-01-9
[3-Benzyloxy-5-benzyloxymethoxymethyl-2-(2-oxo-ethyl)-phenyl]-[(2S,3S)-3-formyl-1-(toluene-4-sulfonyl)-aziridin-2-ylmethyl]-carbamic acid allyl ester

Guidance literature:: With Dess-Martin periodane; In dichloromethane; Ambient temperature;
DOI:10.1016/0040-4039(96)00595-3

Reference yield:

: 98-59-9
p-toluenesulfonyl chloride

: 177958-01-9
[3-Benzyloxy-5-benzyloxymethoxymethyl-2-(2-oxo-ethyl)-phenyl]-[(2S,3S)-3-formyl-1-(toluene-4-sulfonyl)-aziridin-2-ylmethyl]-carbamic acid allyl ester

Guidance literature:: Multi-step reaction with 5 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

5: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / Ambient temperature

With 1H-imidazole; (HF)n*Py; sodium hydride; Dess-Martin periodane; 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

: 177958-01-9
[3-Benzyloxy-5-benzyloxymethoxymethyl-2-(2-oxo-ethyl)-phenyl]-[(2S,3S)-3-formyl-1-(toluene-4-sulfonyl)-aziridin-2-ylmethyl]-carbamic acid allyl ester

Guidance literature:: Multi-step reaction with 7 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

7: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / Ambient temperature

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