[(1R,2S,3S)-2-Benzyloxy-3-hydroxy-1-(4-methoxy-phenoxymethyl)-pent-4-enyl]-carbamic acid tert-butyl ester

Base Information

Chemical Name:[(1R,2S,3S)-2-Benzyloxy-3-hydroxy-1-(4-methoxy-phenoxymethyl)-pent-4-enyl]-carbamic acid tert-butyl ester
CAS No.:825633-62-3
Molecular Formula:C₂₅H₃₃NO₆
Molecular Weight:443.54
Hs Code.:

Synonyms:[(1R,2S,3S)-2-Benzyloxy-3-hydroxy-1-(4-methoxy-phenoxymethyl)-pent-4-enyl]-carbamic acid tert-butyl ester

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Chemical Property of [(1R,2S,3S)-2-Benzyloxy-3-hydroxy-1-(4-methoxy-phenoxymethyl)-pent-4-enyl]-carbamic acid tert-butyl ester

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Technology Process of [(1R,2S,3S)-2-Benzyloxy-3-hydroxy-1-(4-methoxy-phenoxymethyl)-pent-4-enyl]-carbamic acid tert-butyl ester

There total 4 articles about [(1R,2S,3S)-2-Benzyloxy-3-hydroxy-1-(4-methoxy-phenoxymethyl)-pent-4-enyl]-carbamic acid tert-butyl 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: 85.0%

: 1826-67-1
vinyl magnesium bromide

: 851724-09-9
[(1R,2S)-2-Benzyloxy-1-(4-methoxy-phenoxymethyl)-3-oxo-propyl]-carbamic acid tert-butyl ester

: 825633-62-3
[(1R,2S,3S)-2-Benzyloxy-3-hydroxy-1-(4-methoxy-phenoxymethyl)-pent-4-enyl]-carbamic acid tert-butyl ester

Guidance literature:: vinyl magnesium bromide; [(1R,2S)-2-Benzyloxy-1-(4-methoxy-phenoxymethyl)-3-oxo-propyl]-carbamic acid tert-butyl ester; In tetrahydrofuran; at -50 ℃; for 1h;

In tetrahydrofuran; at 20 ℃; for 1h;
DOI:10.1016/j.tetlet.2005.10.074

Reference yield:

: 544455-38-1
ethyl (2E)-4-(4-methoxyphenoxy)but-2-enoate

: 825633-62-3
[(1R,2S,3S)-2-Benzyloxy-3-hydroxy-1-(4-methoxy-phenoxymethyl)-pent-4-enyl]-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 70 percent / LiOH; (DHQD)2PHAL; K₂OsO₄*2H₂O / 2-methyl-propan-2-ol; H₂O / 8 h / 4 °C

2.1: NaH / dimethylformamide / 10 h / 0 °C

2.2: DMAP / tetrahydrofuran / 4 h / Heating

2.3: NH₂NH₂ / methanol / 4 h

3.1: 90 percent / DIBAL / CH₂Cl₂ / 3 h / -78 °C

4.1: tetrahydrofuran / 1 h / -50 °C

4.2: 85 percent / tetrahydrofuran / 1 h / 20 °C

With lithium hydroxide; potassium osmate(VI); sodium hydride; diisobutylaluminium hydride; 1,4-bis(9-O-dihydroquinidine)phthalazine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1016/j.tetlet.2005.10.074

Reference yield:

: 544455-39-2
(2S,3R)-3-Acetylamino-2-hydroxy-4-(4-methoxy-phenoxy)-butyric acid ethyl ester

: 825633-62-3
[(1R,2S,3S)-2-Benzyloxy-3-hydroxy-1-(4-methoxy-phenoxymethyl)-pent-4-enyl]-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaH / dimethylformamide / 10 h / 0 °C

1.2: DMAP / tetrahydrofuran / 4 h / Heating

1.3: NH₂NH₂ / methanol / 4 h

2.1: 90 percent / DIBAL / CH₂Cl₂ / 3 h / -78 °C

3.1: tetrahydrofuran / 1 h / -50 °C

3.2: 85 percent / tetrahydrofuran / 1 h / 20 °C

With sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2005.10.074