(2S)-3-allyloxy-2-tert-butoxycarbonylamino-propionic acid methyl ester

Base Information

• Chemical Name: (2S)-3-allyloxy-2-tert-butoxycarbonylamino-propionic acid methyl ester
• CAS No.: 215167-74-1
• Molecular Formula: C₁₂H₂₁NO₅
• Molecular Weight: 259.302
• Mol file: 215167-74-1.mol

Synonyms:(2S)-3-allyloxy-2-tert-butoxycarbonylamino-propionic acid methyl ester

Chemical Property of (2S)-3-allyloxy-2-tert-butoxycarbonylamino-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (2S)-3-allyloxy-2-tert-butoxycarbonylamino-propionic acid methyl ester

There total 1 articles about (2S)-3-allyloxy-2-tert-butoxycarbonylamino-propionic acid methyl 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:

→ N-tert-butyloxycarbonyl-L-serine methyl ester (2766-43-0) + (2S)-3-allyloxy-2-tert-butoxycarbonylamino-propionic acid methyl ester (215167-74-1)

Guidance literature:

Reference yield:

(2S)-3-allyloxy-2-tert-butoxycarbonylamino-propionic acid methyl ester (215167-74-1) → (S)-2-tert-Butoxycarbonylamino-3-[(E)-4-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-but-2-enyloxy]-propionic acid methyl ester

Guidance literature:

Multi-step reaction with 2 steps

1: [ruthenium benzylidene](PCy₃)2Cl₂ / 48 h / 20 °C / 0.06 - 0.1 Torr

2: [ruthenium benzylidene](PCy₃)2Cl₂ / CH₂Cl₂ / 16 h / Heating

With Grubbs catalyst first generation; In dichloromethane; 1: Addition / 2: Addition;

DOI:10.1021/ja993063u

Reference yield:

(2S)-3-allyloxy-2-tert-butoxycarbonylamino-propionic acid methyl ester (215167-74-1) → (1S,8S,11S,18S)-21,23-bis-(2,4-dimethoxybenzyl)-3,13-dioxa-9,19,21,23-tetraazatricyclo[16.2.2.28,11]tetracosa-5,15-diene-10,20,22,24-tetraone

Guidance literature:

Multi-step reaction with 5 steps

1: 93 percent / TFA / CH₂Cl₂ / 0.5 h / 20 °C

2: 85 percent / NaBH(OAc)3 / CH₂Cl₂ / 2 h / 20 °C

3: 53 percent / HATU; 1-hydroxy-7-azabenzotriazole; N-ethylmorpholine / dimethylformamide; CH₂Cl₂ / 20 °C

4: 42 percent / piperidine / CH₂Cl₂ / 2 h / 20 °C

5: 43 percent / Grubbs catalyst 2nd generation / CH₂Cl₂ / 20 °C

With piperidine; N-ethylmorpholine;; 1-hydroxy-7-aza-benzotriazole; sodium tris(acetoxy)borohydride; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/b416349d

Downstream raw materials:

(2S)-3-allyloxy-2-tert-butoxycarbonylaminopropionic acid

(2S)-3-allyloxy-2-(2,4-dimethoxybenzylamino)-propionic acid methyl ester

(2S)-3-allyloxy-2-(2,4,6-trimethoxybenzylamino)-propionic acid methyl ester

(3S,6S)-3-allyl-6-allyloxymethyl-1-(2,4-dimethoxybenzyl)-piperazine-2,5-dione