methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-(tert-butyldimethyl-silanyloxy)-3-phenylpropionate

Base Information

Chemical Name:methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-(tert-butyldimethyl-silanyloxy)-3-phenylpropionate
CAS No.:323579-86-8
Molecular Formula:C₂₁H₃₅NO₅Si
Molecular Weight:409.598
Hs Code.:

Synonyms:methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-(tert-butyldimethyl-silanyloxy)-3-phenylpropionate

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Chemical Property of methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-(tert-butyldimethyl-silanyloxy)-3-phenylpropionate

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Technology Process of methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-(tert-butyldimethyl-silanyloxy)-3-phenylpropionate

There total 6 articles about methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-(tert-butyldimethyl-silanyloxy)-3-phenylpropionate 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: 100.0%

: 124605-42-1
methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionate

: 18162-48-6
tert-butyldimethylsilyl chloride

: 323579-86-8
methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-(tert-butyldimethyl-silanyloxy)-3-phenylpropionate

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 20h;
DOI:10.1021/ja002700+

Reference yield:

: 60512-85-8
(E)-isopropyl cinnamate

: 323579-86-8
methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-(tert-butyldimethyl-silanyloxy)-3-phenylpropionate

Guidance literature:: Multi-step reaction with 4 steps

1: 76 percent / K₂[OsO₂(OH)4]; LiOH*H₂O; (DHQ)2PHAL / H₂O; 2-methyl-propan-2-ol / 4 h / 4 °C

2: aq. HCl / 15 h / Heating

3: 0.54 g / Et₃N / CH₂Cl₂ / 24.5 h / 0 - 25 °C

4: 91 percent / imidazole; DMAP / CH₂Cl₂ / 10 h / 25 °C

With 1H-imidazole; hydrogenchloride; dmap; lithium hydroxide; Hydroquinone 1,4-phthalazinediyl diether; K2; triethylamine; In dichloromethane; water; tert-butyl alcohol; 1: Sharpless asymmetric aminohydroxylation;
DOI:10.1016/j.tetasy.2005.09.010

Reference yield:

: 140-10-3
(E)-3-phenylacrylic acid

: 323579-86-8
methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-(tert-butyldimethyl-silanyloxy)-3-phenylpropionate

Guidance literature:: Multi-step reaction with 5 steps

1: 76 percent / HCl / 12 h / Heating

2: 76 percent / K₂[OsO₂(OH)4]; LiOH*H₂O; (DHQ)2PHAL / H₂O; 2-methyl-propan-2-ol / 4 h / 4 °C

3: aq. HCl / 15 h / Heating

4: 0.54 g / Et₃N / CH₂Cl₂ / 24.5 h / 0 - 25 °C

5: 91 percent / imidazole; DMAP / CH₂Cl₂ / 10 h / 25 °C

With 1H-imidazole; hydrogenchloride; dmap; lithium hydroxide; Hydroquinone 1,4-phthalazinediyl diether; K2; triethylamine; In dichloromethane; water; tert-butyl alcohol; 2: Sharpless asymmetric aminohydroxylation;
DOI:10.1016/j.tetasy.2005.09.010