(1R,2R)-N-[3-benzyloxymethyl-2-hydroxy-1-(4-methoxybenzyloxymethyl)-3-butenyl]-acetamide

Base Information

Chemical Name:(1R,2R)-N-[3-benzyloxymethyl-2-hydroxy-1-(4-methoxybenzyloxymethyl)-3-butenyl]-acetamide
CAS No.:315719-05-2
Molecular Formula:C₂₃H₂₉NO₅
Molecular Weight:399.487
Hs Code.:

Synonyms:(1R,2R)-N-[3-benzyloxymethyl-2-hydroxy-1-(4-methoxybenzyloxymethyl)-3-butenyl]-acetamide

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Chemical Property of (1R,2R)-N-[3-benzyloxymethyl-2-hydroxy-1-(4-methoxybenzyloxymethyl)-3-butenyl]-acetamide

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Technology Process of (1R,2R)-N-[3-benzyloxymethyl-2-hydroxy-1-(4-methoxybenzyloxymethyl)-3-butenyl]-acetamide

There total 7 articles about (1R,2R)-N-[3-benzyloxymethyl-2-hydroxy-1-(4-methoxybenzyloxymethyl)-3-butenyl]-acetamide 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:

: 315719-01-8
1-[(2R,3S)-2-(1-Benzyloxymethyl-vinyl)-3-(4-methoxy-benzyloxymethyl)-aziridin-1-yl]-ethanone

: 315719-05-2
(1R,2R)-N-[3-benzyloxymethyl-2-hydroxy-1-(4-methoxybenzyloxymethyl)-3-butenyl]-acetamide

Guidance literature:: 1-[(2R,3S)-2-(1-Benzyloxymethyl-vinyl)-3-(4-methoxy-benzyloxymethyl)-aziridin-1-yl]-ethanone; With boron trifluoride diethyl etherate; In tetrahydrofuran; at -25 ℃; for 1.5h;

With water; In tetrahydrofuran; at 20 ℃; for 2h; Further stages.;
DOI:10.1021/ol006736i

Reference yield:

: 315718-85-5
(3R,4R)-3-amino-2-benzyloxymethyl-5-(4-methoxy)benzyloxy-1-pentene-4-ol

: 315719-05-2
(1R,2R)-N-[3-benzyloxymethyl-2-hydroxy-1-(4-methoxybenzyloxymethyl)-3-butenyl]-acetamide

Guidance literature:: Multi-step reaction with 4 steps

1: 63 percent / PPh₃; diisopropyl azodicarboxylate / tetrahydrofuran / 17 h / Heating

2: Et₃N / DMAP / CH₂Cl₂ / -78 °C

3: BF₃*Et₂O / tetrahydrofuran / 1.5 h / -25 °C

4: H₂O / tetrahydrofuran / 2 h / 20 °C

With di-isopropyl azodicarboxylate; boron trifluoride diethyl etherate; water; triethylamine; triphenylphosphine; dmap; In tetrahydrofuran; dichloromethane; 1: Mitsunobu reaction;
DOI:10.1021/jo0262053

Reference yield:

: 315718-83-3
(2S,3S)-2-(1-Benzyloxymethyl-vinyl)-3-(4-methoxy-benzyloxymethyl)-oxirane

: 315719-05-2
(1R,2R)-N-[3-benzyloxymethyl-2-hydroxy-1-(4-methoxybenzyloxymethyl)-3-butenyl]-acetamide

Guidance literature:: Multi-step reaction with 5 steps

1: 84 percent / aq. NH₃ / 0.13 h / Heating

2: 63 percent / PPh₃; diisopropyl azodicarboxylate / tetrahydrofuran / 17 h / Heating

3: Et₃N / DMAP / CH₂Cl₂ / -78 °C

4: BF₃*Et₂O / tetrahydrofuran / 1.5 h / -25 °C

5: H₂O / tetrahydrofuran / 2 h / 20 °C

With ammonium hydroxide; di-isopropyl azodicarboxylate; boron trifluoride diethyl etherate; water; triethylamine; triphenylphosphine; dmap; In tetrahydrofuran; dichloromethane; 2: Mitsunobu reaction;
DOI:10.1021/jo0262053