tert-butyl (2R,3R,αR)-3--2-hydroxy-3-phenylpropionate

Base Information

Chemical Name:tert-butyl (2R,3R,αR)-3--2-hydroxy-3-phenylpropionate
CAS No.:151671-03-3
Molecular Formula:C₂₈H₃₃NO₃
Molecular Weight:431.575
Hs Code.:

tert-butyl (2R,3R,αR)-3-<N-benzyl-N-(α-methylbenzyl)amino>-2-hydroxy-3-phenylpropionate

Synonyms:tert-butyl (2R,3R,αR)-3--2-hydroxy-3-phenylpropionate

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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 tert-butyl (2R,3R,αR)-3--2-hydroxy-3-phenylpropionate

Chemical Property:

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Technology Process of tert-butyl (2R,3R,αR)-3--2-hydroxy-3-phenylpropionate

There total 6 articles about tert-butyl (2R,3R,αR)-3--2-hydroxy-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: 93.0%

: 14990-09-1
tert-butyl cinnamate

: 38235-77-7
(R)-N-benzyl-1-phenylethylamine

: 151671-03-3
tert-butyl (2R,3R,αR)-3--2-hydroxy-3-phenylpropionate

Guidance literature:: (R)-N-benzyl-1-phenylethylamine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

tert-butyl cinnamate; In tetrahydrofuran; hexane; at -78 ℃; for 2h;

With (1R)-(?)-(10-camphorsulfonyl)oxaziridine; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 14h; diastereoselective reaction;
DOI:10.1016/j.tet.2014.06.057

Reference yield: 31.0%

: 161453-17-4
tert-butyl (3R,αR)-3--2-oxo-3-phenylpropionate

: 151671-03-3
tert-butyl (2R,3R,αR)-3--2-hydroxy-3-phenylpropionate

: tert-butyl (2S,3R,αR)-3--2-hydroxy-3-phenylpropionate

Guidance literature:: With methanol; sodium tetrahydroborate; at -20 ℃; for 2h; diastereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tet.2013.08.007

Reference yield:

: 100-52-7
benzaldehyde

: 151671-03-3
tert-butyl (2R,3R,αR)-3--2-hydroxy-3-phenylpropionate

Guidance literature:: Multi-step reaction with 5 steps

1.1: methylmagnesium bromide / 0.25 h / 20 °C

1.2: 2.5 h / 67 °C

2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

2.2: 2 h / -78 °C

2.3: 16 h / -78 - 20 °C

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C

3.2: 0.5 h / -78 - 20 °C

4.1: diisobutylaluminium hydride / tetrahydrofuran / 2 h / -20 °C

5.1: Methanesulfonic anhydride; triethylamine / dichloromethane / 1 h / 20 °C

5.2: 24 h / 40 °C

With n-butyllithium; oxalyl dichloride; methylmagnesium bromide; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; Methanesulfonic anhydride; In tetrahydrofuran; dichloromethane; 3.1: |Swern Oxidation / 3.2: |Swern Oxidation;
DOI:10.1016/j.tet.2018.04.071