(Z)-2-[(2R,3R)-3-((R)-1-Acetoxy-ethyl)-2-methanesulfonyloxymethyl-4-oxo-azetidin-1-yl]-3-hydroxy-but-2-enoic acid benzyl ester

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Chemical Name:(Z)-2-[(2R,3R)-3-((R)-1-Acetoxy-ethyl)-2-methanesulfonyloxymethyl-4-oxo-azetidin-1-yl]-3-hydroxy-but-2-enoic acid benzyl ester
CAS No.:733769-93-2
Molecular Formula:C₂₀H₂₅NO₉S
Molecular Weight:455.486
Hs Code.:

Synonyms:(Z)-2-[(2R,3R)-3-((R)-1-Acetoxy-ethyl)-2-methanesulfonyloxymethyl-4-oxo-azetidin-1-yl]-3-hydroxy-but-2-enoic acid benzyl ester

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Chemical Property of (Z)-2-[(2R,3R)-3-((R)-1-Acetoxy-ethyl)-2-methanesulfonyloxymethyl-4-oxo-azetidin-1-yl]-3-hydroxy-but-2-enoic acid benzyl ester

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Technology Process of (Z)-2-[(2R,3R)-3-((R)-1-Acetoxy-ethyl)-2-methanesulfonyloxymethyl-4-oxo-azetidin-1-yl]-3-hydroxy-but-2-enoic acid benzyl ester

There total 3 articles about (Z)-2-[(2R,3R)-3-((R)-1-Acetoxy-ethyl)-2-methanesulfonyloxymethyl-4-oxo-azetidin-1-yl]-3-hydroxy-but-2-enoic 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: 47.0%

: 93552-78-4
benzyl 2,3-dioxobutanoate

: 733769-92-1
(αR,3R,4R)-3-(1-acetoxyethyl)-4-(mesyloxymethyl)-azetidin-2-one

: 733769-93-2
(Z)-2-[(2R,3R)-3-((R)-1-Acetoxy-ethyl)-2-methanesulfonyloxymethyl-4-oxo-azetidin-1-yl]-3-hydroxy-but-2-enoic acid benzyl ester

Guidance literature:: benzyl 2,3-dioxobutanoate; (αR,3R,4R)-3-(1-acetoxyethyl)-4-(mesyloxymethyl)-azetidin-2-one; With triethylamine; In tetrahydrofuran; at 20 ℃; for 0.5h;

With pyridine; thionyl chloride; In tetrahydrofuran; at -25 ℃; for 1h;

With zinc; In water; acetic acid; at 4 ℃; for 1h;
DOI:10.1007/s00706-003-0135-9

Reference yield:

: 341554-36-7
(αR,3R,4R)-3-(1-acetoxyethyl)-4-hydroxymethyl-N-(4-methoxyphenyl)-azetidin-2-one

: 733769-93-2
(Z)-2-[(2R,3R)-3-((R)-1-Acetoxy-ethyl)-2-methanesulfonyloxymethyl-4-oxo-azetidin-1-yl]-3-hydroxy-but-2-enoic acid benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 76 percent / pyridine / -5 - 25 °C

2.1: 73 percent / ammonium cerium(IV) nitrate / H₂O; acetonitrile / 2 h / -10 - 0 °C

3.1: Et₃N / tetrahydrofuran / 0.5 h / 20 °C

3.2: pyridine; thionyl chloride / tetrahydrofuran / 1 h / -25 °C

3.3: 47 percent / Zn powder / acetic acid; H₂O / 1 h / 4 °C

With ammonium cerium(IV) nitrate; triethylamine; In tetrahydrofuran; pyridine; water; acetonitrile;
DOI:10.1007/s00706-003-0135-9

Reference yield:

: 733769-91-0
(αR,3R,4R)-3-(1-acetoxyethyl)-4-(mesyloxymethyl)-N-(4-methoxyphenyl)-azetidin-2-one

: 733769-93-2
(Z)-2-[(2R,3R)-3-((R)-1-Acetoxy-ethyl)-2-methanesulfonyloxymethyl-4-oxo-azetidin-1-yl]-3-hydroxy-but-2-enoic acid benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 73 percent / ammonium cerium(IV) nitrate / H₂O; acetonitrile / 2 h / -10 - 0 °C

2.1: Et₃N / tetrahydrofuran / 0.5 h / 20 °C

2.2: pyridine; thionyl chloride / tetrahydrofuran / 1 h / -25 °C

2.3: 47 percent / Zn powder / acetic acid; H₂O / 1 h / 4 °C

With ammonium cerium(IV) nitrate; triethylamine; In tetrahydrofuran; water; acetonitrile;
DOI:10.1007/s00706-003-0135-9