(2R,3S)-2-[(R)-Amino-(4-methoxy-phenyl)-methyl]-3-benzo[1,3]dioxol-5-yl-4-hydroxy-butyric acid methyl ester

Base Information

Chemical Name:(2R,3S)-2-[(R)-Amino-(4-methoxy-phenyl)-methyl]-3-benzo[1,3]dioxol-5-yl-4-hydroxy-butyric acid methyl ester
CAS No.:250583-08-5
Molecular Formula:C₂₀H₂₃NO₆
Molecular Weight:373.406
Hs Code.:

Synonyms:(2R,3S)-2-[(R)-Amino-(4-methoxy-phenyl)-methyl]-3-benzo[1,3]dioxol-5-yl-4-hydroxy-butyric acid methyl ester

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Chemical Property of (2R,3S)-2-[(R)-Amino-(4-methoxy-phenyl)-methyl]-3-benzo[1,3]dioxol-5-yl-4-hydroxy-butyric acid methyl ester

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Technology Process of (2R,3S)-2-[(R)-Amino-(4-methoxy-phenyl)-methyl]-3-benzo[1,3]dioxol-5-yl-4-hydroxy-butyric acid methyl ester

There total 10 articles about (2R,3S)-2-[(R)-Amino-(4-methoxy-phenyl)-methyl]-3-benzo[1,3]dioxol-5-yl-4-hydroxy-butyric 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: 100.0%

: 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

: 250583-08-5
(2R,3S)-2-[(R)-Amino-(4-methoxy-phenyl)-methyl]-3-benzo[1,3]dioxol-5-yl-4-hydroxy-butyric acid methyl ester

Guidance literature:: With acetic acid; zinc; In tetrahydrofuran;
DOI:10.1016/S0040-4039(99)01497-5

Reference yield:

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

: 250583-08-5
(2R,3S)-2-[(R)-Amino-(4-methoxy-phenyl)-methyl]-3-benzo[1,3]dioxol-5-yl-4-hydroxy-butyric acid methyl ester

Guidance literature:: Multi-step reaction with 10 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

10: 100 percent / Zn; AcOH / tetrahydrofuran

With dmap; n-butyllithium; borane-THF; lithium hydroperoxide; tributyl-amine; trimethylsilyl trifluoromethanesulfonate; water; sodium hexamethyldisilazane; caesium carbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; zinc; 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 / 10: Ring cleavage;
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

: 250583-08-5
(2R,3S)-2-[(R)-Amino-(4-methoxy-phenyl)-methyl]-3-benzo[1,3]dioxol-5-yl-4-hydroxy-butyric acid methyl ester

Guidance literature:: Multi-step reaction with 6 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

6: 100 percent / Zn; AcOH / tetrahydrofuran

With dmap; borane-THF; tributyl-amine; trimethylsilyl trifluoromethanesulfonate; caesium carbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; zinc; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; acetonitrile; 1: Reduction / 2: Condensation / 3: Condensation / 4: Esterification / 5: Cyclization / 6: Ring cleavage;
DOI:10.1016/S0040-4039(99)01497-5