(R)-3-(benzyloxycarbonyl)-2,2-dimethyl-4-<(E)-3-hydroxy-1-propenyl>oxazolidine

Base Information

Chemical Name:(R)-3-(benzyloxycarbonyl)-2,2-dimethyl-4-<(E)-3-hydroxy-1-propenyl>oxazolidine
CAS No.:174271-50-2
Molecular Formula:C₁₆H₂₁NO₄
Molecular Weight:291.347
Hs Code.:

Synonyms:(R)-3-(benzyloxycarbonyl)-2,2-dimethyl-4-<(E)-3-hydroxy-1-propenyl>oxazolidine

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Chemical Property of (R)-3-(benzyloxycarbonyl)-2,2-dimethyl-4-<(E)-3-hydroxy-1-propenyl>oxazolidine

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Technology Process of (R)-3-(benzyloxycarbonyl)-2,2-dimethyl-4-<(E)-3-hydroxy-1-propenyl>oxazolidine

There total 5 articles about (R)-3-(benzyloxycarbonyl)-2,2-dimethyl-4-<(E)-3-hydroxy-1-propenyl>oxazolidine 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: 79.0%

: 321658-31-5
(R)-3-(benzyloxycarbonyl)-2,2-dimethyl-4-<(E)-2-carbomethoxyvinyl>oxazolidine

: 174271-50-2
(R)-3-(benzyloxycarbonyl)-2,2-dimethyl-4-<(E)-3-hydroxy-1-propenyl>oxazolidine

Guidance literature:: With diisobutylaluminium hydride; In tetrahydrofuran; hexane; at -78 ℃; for 2h;
DOI:10.1021/jo9517914

Reference yield:

: 1676-81-9
N-benzyloxycarbonyl-L-serine methyl ester

: 174271-50-2
(R)-3-(benzyloxycarbonyl)-2,2-dimethyl-4-<(E)-3-hydroxy-1-propenyl>oxazolidine

Guidance literature:: Multi-step reaction with 4 steps

1: 95 percent / BF₃*Et₂O / acetone / 25 h

2: 75 percent / DIBAL-H / toluene / 4 h / -78 °C

3: 1.) NaH / 1.) THF, 30 min, 2.) 1 h

4: 79 percent / DIBAL-H / tetrahydrofuran; hexane / 2 h / -78 °C

With boron trifluoride diethyl etherate; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; hexane; acetone; toluene;
DOI:10.1021/jo9517914

Reference yield:

: 1145-80-8
N-(benzyloxycarbonyl)-L-serine

: 174271-50-2
(R)-3-(benzyloxycarbonyl)-2,2-dimethyl-4-<(E)-3-hydroxy-1-propenyl>oxazolidine

Guidance literature:: Multi-step reaction with 5 steps

1: 95 percent / SOCl₂ / 24 h / Ambient temperature

2: 95 percent / BF₃*Et₂O / acetone / 25 h

3: 75 percent / DIBAL-H / toluene / 4 h / -78 °C

4: 1.) NaH / 1.) THF, 30 min, 2.) 1 h

5: 79 percent / DIBAL-H / tetrahydrofuran; hexane / 2 h / -78 °C

With thionyl chloride; boron trifluoride diethyl etherate; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; hexane; acetone; toluene;
DOI:10.1021/jo9517914