3-[(2S)-2-(tert-butoxycarbonylamino)-3-(benzyloxy)propanoxy]-(2S)-1-(tert-butyldiphenylsilyloxy)-2-(methanesulfonyloxy)propane

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Chemical Name:3-[(2S)-2-(tert-butoxycarbonylamino)-3-(benzyloxy)propanoxy]-(2S)-1-(tert-butyldiphenylsilyloxy)-2-(methanesulfonyloxy)propane
CAS No.:651031-17-3
Molecular Formula:C₃₅H₄₉NO₈SSi
Molecular Weight:671.927
Hs Code.:

Synonyms:3-[(2S)-2-(tert-butoxycarbonylamino)-3-(benzyloxy)propanoxy]-(2S)-1-(tert-butyldiphenylsilyloxy)-2-(methanesulfonyloxy)propane

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Chemical Property of 3-[(2S)-2-(tert-butoxycarbonylamino)-3-(benzyloxy)propanoxy]-(2S)-1-(tert-butyldiphenylsilyloxy)-2-(methanesulfonyloxy)propane

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Technology Process of 3-[(2S)-2-(tert-butoxycarbonylamino)-3-(benzyloxy)propanoxy]-(2S)-1-(tert-butyldiphenylsilyloxy)-2-(methanesulfonyloxy)propane

There total 8 articles about 3-[(2S)-2-(tert-butoxycarbonylamino)-3-(benzyloxy)propanoxy]-(2S)-1-(tert-butyldiphenylsilyloxy)-2-(methanesulfonyloxy)propane 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%

: 124-63-0
methanesulfonyl chloride

: 651031-16-2
3-[(2S)-2-(tert-butoxycarbonylamino)-3-(benzyloxy)propanoxy]-(2S)-1-(tert-butyldiphenylsilyloxy)propan-2-ol

: 651031-17-3
3-[(2S)-2-(tert-butoxycarbonylamino)-3-(benzyloxy)propanoxy]-(2S)-1-(tert-butyldiphenylsilyloxy)-2-(methanesulfonyloxy)propane

Guidance literature:: With dmap; triethylamine; In dichloromethane; at -30 ℃;
DOI:10.1021/ol035998s

Reference yield:

: 79069-15-1
N-(tert-butyloxycarbonyl)-O-benzyl-L-serinol

: 651031-17-3
3-[(2S)-2-(tert-butoxycarbonylamino)-3-(benzyloxy)propanoxy]-(2S)-1-(tert-butyldiphenylsilyloxy)-2-(methanesulfonyloxy)propane

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / tetrahydrofuran / 0.25 h / cooling

1.2: 81 percent / tetrahydrofuran / 2.17 h

2.1: 84 percent / aq. AcOH / 24 h / 20 °C

3.1: 88 percent / imidazole / dimethylformamide / 2 h / 20 °C

4.1: 93 percent / Et₃N; DMAP / CH₂Cl₂ / -30 °C

With 1H-imidazole; dmap; sodium hydride; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol035998s

Reference yield:

: 95715-85-8
2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester

: 651031-17-3
3-[(2S)-2-(tert-butoxycarbonylamino)-3-(benzyloxy)propanoxy]-(2S)-1-(tert-butyldiphenylsilyloxy)-2-(methanesulfonyloxy)propane

Guidance literature:: Multi-step reaction with 8 steps

1.1: pyridinium p-toluenesulfonate / CH₂Cl₂

2.1: LiBH₄ / diethyl ether

3.1: NaH; TBAI / tetrahydrofuran

4.1: pyridinium p-toluenesulfonate / ethanol / 60 °C

5.1: NaH / tetrahydrofuran / 0.25 h / cooling

5.2: 81 percent / tetrahydrofuran / 2.17 h

6.1: 84 percent / aq. AcOH / 24 h / 20 °C

7.1: 88 percent / imidazole / dimethylformamide / 2 h / 20 °C

8.1: 93 percent / Et₃N; DMAP / CH₂Cl₂ / -30 °C

With 1H-imidazole; dmap; lithium borohydride; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; triethylamine; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol035998s