(S)-2-[(1R,2R)-2-Acetoxy-1-(4-methoxy-benzyloxy)-but-3-enyl]-aziridine-1-carboxylic acid benzyl ester

Base Information

Chemical Name:(S)-2-[(1R,2R)-2-Acetoxy-1-(4-methoxy-benzyloxy)-but-3-enyl]-aziridine-1-carboxylic acid benzyl ester
CAS No.:207679-28-5
Molecular Formula:C₂₄H₂₇NO₆
Molecular Weight:425.481
Hs Code.:

Synonyms:(S)-2-[(1R,2R)-2-Acetoxy-1-(4-methoxy-benzyloxy)-but-3-enyl]-aziridine-1-carboxylic acid benzyl ester

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Chemical Property of (S)-2-[(1R,2R)-2-Acetoxy-1-(4-methoxy-benzyloxy)-but-3-enyl]-aziridine-1-carboxylic acid benzyl ester

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Technology Process of (S)-2-[(1R,2R)-2-Acetoxy-1-(4-methoxy-benzyloxy)-but-3-enyl]-aziridine-1-carboxylic acid benzyl ester

There total 11 articles about (S)-2-[(1R,2R)-2-Acetoxy-1-(4-methoxy-benzyloxy)-but-3-enyl]-aziridine-1-carboxylic acid benzyl 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%

: 207679-27-4
Acetic acid (1R,2S,3R)-4-benzyloxycarbonylamino-3-methanesulfonyloxy-2-(4-methoxy-benzyloxy)-1-vinyl-butyl ester

: 207679-28-5
(S)-2-[(1R,2R)-2-Acetoxy-1-(4-methoxy-benzyloxy)-but-3-enyl]-aziridine-1-carboxylic acid benzyl ester

Guidance literature:: With potassium tert-butylate; In tetrahydrofuran; at -78 ℃;
DOI:10.1021/ja9801386

Reference yield:

: 112531-79-0
(3R,4R)-4-(methoxymethoxy)hexa-1,5-dien-3-ol

: 207679-28-5
(S)-2-[(1R,2R)-2-Acetoxy-1-(4-methoxy-benzyloxy)-but-3-enyl]-aziridine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 90 percent / L-(+)-DIPT; t-BuOOH; Ti(O-i-Pr)4 / -10 °C

2: 84 percent / NaH

3: 74 percent / NaN₃; aq. NH₄Cl / 2-methoxy-ethanol

4: Ph₃P; H₂O / toluene

5: Et₃N

6: 96 percent / Et₃N

7: 74 percent / HCl; MeOH

8: 99 percent / pyridine

9: 100 percent / KO-t-Bu / tetrahydrofuran / -50 °C

With pyridine; titanium(IV) isopropylate; hydrogenchloride; methanol; tert.-butylhydroperoxide; sodium azide; L-(+)-diisopropyl tartrate; potassium tert-butylate; water; sodium hydride; ammonium chloride; triethylamine; triphenylphosphine; In tetrahydrofuran; 2-methoxy-ethanol; toluene; 1: asymmetric epoxidation / 2: Alkylation / 3: Addition / 4: Reduction / 5: N-acylation / 6: mesylation / 7: methanolysis / 8: Acetylation / 9: Cyclization;
DOI:10.1021/ja992274w

Reference yield:

: 207679-21-8
(1S,2R)-2-(methoxymethoxy)-1-((R)-oxiran-2-yl)but-3-en-1-ol

: 207679-28-5
(S)-2-[(1R,2R)-2-Acetoxy-1-(4-methoxy-benzyloxy)-but-3-enyl]-aziridine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 84 percent / NaH

2: 74 percent / NaN₃; aq. NH₄Cl / 2-methoxy-ethanol

3: Ph₃P; H₂O / toluene

4: Et₃N

5: 96 percent / Et₃N

6: 74 percent / HCl; MeOH

7: 99 percent / pyridine

8: 100 percent / KO-t-Bu / tetrahydrofuran / -50 °C

With pyridine; hydrogenchloride; methanol; sodium azide; potassium tert-butylate; water; sodium hydride; ammonium chloride; triethylamine; triphenylphosphine; In tetrahydrofuran; 2-methoxy-ethanol; toluene; 1: Alkylation / 2: Addition / 3: Reduction / 4: N-acylation / 5: mesylation / 6: methanolysis / 7: Acetylation / 8: Cyclization;
DOI:10.1021/ja992274w