(3R,4R,5S)-5-Benzo[1,3]dioxol-5-yl-3-(4-methoxy-phenyl)-[1,2]oxazinane-4-carboxylic acid methyl ester

Base Information

Chemical Name:(3R,4R,5S)-5-Benzo[1,3]dioxol-5-yl-3-(4-methoxy-phenyl)-[1,2]oxazinane-4-carboxylic acid methyl ester
CAS No.:250583-06-3
Molecular Formula:C₂₀H₂₁NO₆
Molecular Weight:371.39
Hs Code.:

Synonyms:(3R,4R,5S)-5-Benzo[1,3]dioxol-5-yl-3-(4-methoxy-phenyl)-[1,2]oxazinane-4-carboxylic acid methyl ester

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Chemical Property of (3R,4R,5S)-5-Benzo[1,3]dioxol-5-yl-3-(4-methoxy-phenyl)-[1,2]oxazinane-4-carboxylic acid methyl ester

Chemical Property:

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Technology Process of (3R,4R,5S)-5-Benzo[1,3]dioxol-5-yl-3-(4-methoxy-phenyl)-[1,2]oxazinane-4-carboxylic acid methyl ester

There total 9 articles about (3R,4R,5S)-5-Benzo[1,3]dioxol-5-yl-3-(4-methoxy-phenyl)-[1,2]oxazinane-4-carboxylic 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:

: 250583-05-2
(S)-3-Benzo[1,3]dioxol-5-yl-4-[1-(4-methoxy-phenyl)-meth-(E)-ylideneaminooxy]-butyric acid methyl ester

: (3S,5S)-5-Benzo[1,3]dioxol-5-yl-3-(4-methoxy-phenyl)-[1,2]oxazinane-4-carboxylic acid methyl ester

: 250583-06-3
(3R,4R,5S)-5-Benzo[1,3]dioxol-5-yl-3-(4-methoxy-phenyl)-[1,2]oxazinane-4-carboxylic acid methyl ester

Guidance literature:: With tributyl-amine; trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 20 ℃;
DOI:10.1016/S0040-4039(99)01497-5

Reference yield:

: 2861-28-1
1,3-benzodioxole-5-acetic acid

: 250583-06-3
(3R,4R,5S)-5-Benzo[1,3]dioxol-5-yl-3-(4-methoxy-phenyl)-[1,2]oxazinane-4-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: Et₃N / diethyl ether / -78 - 0 °C

2: 70 percent / BuLi / tetrahydrofuran / -78 °C

3: 76 percent / NaHMDS / tetrahydrofuran / -78 - 50 °C

4: 92 percent / LiOOH; water / tetrahydrofuran / 0 - 20 °C

5: 99 percent / BH₃*THF / 0 - 20 °C

6: 95 percent / Et₃N; DMAP / CH₂Cl₂

7: 79 percent / Cs₂CO₃ / acetonitrile / Heating

8: 98 percent / pTSA / methanol / Heating

9: TMSOTf; Bu₃N / 1,2-dichloro-ethane / 20 °C

With dmap; n-butyllithium; borane-THF; lithium hydroperoxide; tributyl-amine; trimethylsilyl trifluoromethanesulfonate; water; sodium hexamethyldisilazane; caesium carbonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1,2-dichloro-ethane; acetonitrile; 1: Acylation / 2: Acylation / 3: Alkylation / 4: Hydrolysis / 5: Reduction / 6: Condensation / 7: Condensation / 8: Esterification / 9: Cyclization;
DOI:10.1016/S0040-4039(99)01497-5

Reference yield:

: 250583-00-7
(S)-2-Benzo[1,3]dioxol-5-yl-succinic acid 4-tert-butyl ester

: 250583-06-3
(3R,4R,5S)-5-Benzo[1,3]dioxol-5-yl-3-(4-methoxy-phenyl)-[1,2]oxazinane-4-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 99 percent / BH₃*THF / 0 - 20 °C

2: 95 percent / Et₃N; DMAP / CH₂Cl₂

3: 79 percent / Cs₂CO₃ / acetonitrile / Heating

4: 98 percent / pTSA / methanol / Heating

5: TMSOTf; Bu₃N / 1,2-dichloro-ethane / 20 °C

With dmap; borane-THF; tributyl-amine; trimethylsilyl trifluoromethanesulfonate; caesium carbonate; toluene-4-sulfonic acid; triethylamine; In methanol; dichloromethane; 1,2-dichloro-ethane; acetonitrile; 1: Reduction / 2: Condensation / 3: Condensation / 4: Esterification / 5: Cyclization;
DOI:10.1016/S0040-4039(99)01497-5