methanesulfonate of (3R,4S)-4-[(R)-1-hydroxy-3-butenyl]-1-(p-methoxyphenyl)-3-(2-propenyloxy)-2-azetidinone

Base Information

• Chemical Name: methanesulfonate of (3R,4S)-4-[(R)-1-hydroxy-3-butenyl]-1-(p-methoxyphenyl)-3-(2-propenyloxy)-2-azetidinone
• CAS No.: 277758-04-0
• Molecular Formula: C₁₈H₂₃NO₆S
• Molecular Weight: 381.45

Synonyms:methanesulfonate of (3R,4S)-4-[(R)-1-hydroxy-3-butenyl]-1-(p-methoxyphenyl)-3-(2-propenyloxy)-2-azetidinone

Chemical Property of methanesulfonate of (3R,4S)-4-[(R)-1-hydroxy-3-butenyl]-1-(p-methoxyphenyl)-3-(2-propenyloxy)-2-azetidinone

Chemical Property:

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Technology Process of methanesulfonate of (3R,4S)-4-[(R)-1-hydroxy-3-butenyl]-1-(p-methoxyphenyl)-3-(2-propenyloxy)-2-azetidinone

There total 7 articles about methanesulfonate of (3R,4S)-4-[(R)-1-hydroxy-3-butenyl]-1-(p-methoxyphenyl)-3-(2-propenyloxy)-2-azetidinone 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: 92.0%

methanesulfonyl chloride (124-63-0) + (3R,4S)-4-[(R)-1-hydroxy-3-butenyl]-1-(p-methoxyphenyl)-3-(2-propenyloxy)-2-azetidinone (277757-95-6) → methanesulfonate of (3R,4S)-4-[(R)-1-hydroxy-3-butenyl]-1-(p-methoxyphenyl)-3-(2-propenyloxy)-2-azetidinone (277758-04-0)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/jo991641j

Reference yield:

N-(p-anisyl)-4-<(S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl>-methylene-imine (103239-04-9) → methanesulfonate of (3R,4S)-4-[(R)-1-hydroxy-3-butenyl]-1-(p-methoxyphenyl)-3-(2-propenyloxy)-2-azetidinone (277758-04-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 95 percent / Et₃N / CH₂Cl₂ / 16 h / 20 °C

2: 95 percent / sodium methoxide / methanol / 0.33 h / 20 °C

3: 70 percent / sodium hydroxide; tetrabutyl ammonium iodide / CH₂Cl₂; H₂O / 20 h / 20 °C

4: 100 percent / p-TsOH*H₂O / tetrahydrofuran; H₂O / 2 h / Heating

5: sodium hydrogen carbonate; sodium periodate / CH₂Cl₂; H₂O / 2 h

6: 71 percent / SnCl₄ / CH₂Cl₂ / 0.75 h / -78 °C

7: 92 percent / Et₃N / CH₂Cl₂ / 2 h / 20 °C

With sodium hydroxide; sodium periodate; sodium methylate; tin(IV) chloride; tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; 1: Staudinger reaction / 2: Deacetylation / 3: Alkylation / 4: Hydrolysis / 5: oxidative cleavage / 6: Addition / 7: Substitution;

DOI:10.1021/jo991641j

Reference yield:

(3R,4S)-cis-1-(p-anisyl)-3-hydroxy-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one (115828-87-0) → methanesulfonate of (3R,4S)-4-[(R)-1-hydroxy-3-butenyl]-1-(p-methoxyphenyl)-3-(2-propenyloxy)-2-azetidinone (277758-04-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 70 percent / sodium hydroxide; tetrabutyl ammonium iodide / CH₂Cl₂; H₂O / 20 h / 20 °C

2: 100 percent / p-TsOH*H₂O / tetrahydrofuran; H₂O / 2 h / Heating

3: sodium hydrogen carbonate; sodium periodate / CH₂Cl₂; H₂O / 2 h

4: 71 percent / SnCl₄ / CH₂Cl₂ / 0.75 h / -78 °C

5: 92 percent / Et₃N / CH₂Cl₂ / 2 h / 20 °C

With sodium hydroxide; sodium periodate; tin(IV) chloride; tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; dichloromethane; water; 1: Alkylation / 2: Hydrolysis / 3: oxidative cleavage / 4: Addition / 5: Substitution;

DOI:10.1021/jo991641j

upstream raw materials:

methanesulfonyl chloride

(3R,4S)-4-[(R)-1-hydroxy-3-butenyl]-1-(p-methoxyphenyl)-3-(2-propenyloxy)-2-azetidinone

N-(p-anisyl)-4-<(S)-2',2'-dimethyl-1',3'-dioxolan-4'-yl>-methylene-imine

(3R,4S)-cis-1-(p-anisyl)-3-hydroxy-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one

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