Methanesulfonic acid (1R,3R)-3-allyloxycarbonylamino-3-[4-(allyloxycarbonylamino-methyl)-phenyl]-1-methanesulfonyloxymethyl-propyl ester

Base Information

• Chemical Name: Methanesulfonic acid (1R,3R)-3-allyloxycarbonylamino-3-[4-(allyloxycarbonylamino-methyl)-phenyl]-1-methanesulfonyloxymethyl-propyl ester
• CAS No.: 263155-24-4
• Molecular Formula: C₂₁H₃₀N₂O₁₀S₂
• Molecular Weight: 534.609

Synonyms:Methanesulfonic acid (1R,3R)-3-allyloxycarbonylamino-3-[4-(allyloxycarbonylamino-methyl)-phenyl]-1-methanesulfonyloxymethyl-propyl ester

Chemical Property of Methanesulfonic acid (1R,3R)-3-allyloxycarbonylamino-3-[4-(allyloxycarbonylamino-methyl)-phenyl]-1-methanesulfonyloxymethyl-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methanesulfonic acid (1R,3R)-3-allyloxycarbonylamino-3-[4-(allyloxycarbonylamino-methyl)-phenyl]-1-methanesulfonyloxymethyl-propyl ester

There total 29 articles about Methanesulfonic acid (1R,3R)-3-allyloxycarbonylamino-3-[4-(allyloxycarbonylamino-methyl)-phenyl]-1-methanesulfonyloxymethyl-propyl 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:

methanesulfonyl chloride (124-63-0) + (1R,3R)-N-allyloxycarbonyl-1-(4-N-allyloxycarbonylaminomethyl)phenyl-3,4-O-isopropylidene-3,4-dihydroxybutylamine (263155-21-1) → Methanesulfonic acid (1R,3R)-3-allyloxycarbonylamino-3-[4-(allyloxycarbonylamino-methyl)-phenyl]-1-methanesulfonyloxymethyl-propyl ester (263155-24-4)

Guidance literature:

With TEA; In dichloromethane; at 0 ℃;

DOI:10.1016/S0960-894X(99)00657-5

Reference yield:

4-(tert-butyldimethylsiloxymethyl)bromobenzene (87736-74-1) → Methanesulfonic acid (1R,3R)-3-allyloxycarbonylamino-3-[4-(allyloxycarbonylamino-methyl)-phenyl]-1-methanesulfonyloxymethyl-propyl ester (263155-24-4)

Guidance literature:

Multi-step reaction with 14 steps

1: 88 percent / n-BuLi / tetrahydrofuran / -70 °C

2: 88 percent / tetrapropylammonium perruthenate; 4-methylmorpholine / CH₂Cl₂

3: NaBH₄ / methanol / 0 °C

4: TEA / CH₂Cl₂ / 0 °C

5: NaN₃ / dimethylformamide / 50 °C

6: PPh₃; water / tetrahydrofuran / 20 °C

7: TEA / tetrahydrofuran / 0 °C

8: n-Bu₄NF / tetrahydrofuran / 0 °C

9: TEA / CH₂Cl₂ / 0 °C

10: NaN₃ / dimethylformamide / 20 °C

11: PPh₃; H₂₀ / tetrahydrofuran / 20 °C

12: TEA / tetrahydrofuran / 0 °C

13: p-TsOH / methanol / 20 °C

14: TEA / CH₂Cl₂ / 0 °C

With 4-methyl-morpholine; sodium tetrahydroborate; n-butyllithium; sodium azide; tetrapropylammonium perruthennate; TEA; tetrabutyl ammonium fluoride; water; toluene-4-sulfonic acid; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.48.310

Reference yield:

(3R)-1-(4-tert-butyldimethylsiloxymethylphenyl)-3,4-O-isopropylidene-3,4-dihydroxybutanol (228267-27-4) → Methanesulfonic acid (1R,3R)-3-allyloxycarbonylamino-3-[4-(allyloxycarbonylamino-methyl)-phenyl]-1-methanesulfonyloxymethyl-propyl ester (263155-24-4)

Guidance literature:

Multi-step reaction with 13 steps

1: 88 percent / tetrapropylammonium perruthenate; 4-methylmorpholine / CH₂Cl₂

2: NaBH₄ / methanol / 0 °C

3: TEA / CH₂Cl₂ / 0 °C

4: NaN₃ / dimethylformamide / 50 °C

5: PPh₃; water / tetrahydrofuran / 20 °C

6: TEA / tetrahydrofuran / 0 °C

7: n-Bu₄NF / tetrahydrofuran / 0 °C

8: TEA / CH₂Cl₂ / 0 °C

9: NaN₃ / dimethylformamide / 20 °C

10: PPh₃; H₂₀ / tetrahydrofuran / 20 °C

11: TEA / tetrahydrofuran / 0 °C

12: p-TsOH / methanol / 20 °C

13: TEA / CH₂Cl₂ / 0 °C

With 4-methyl-morpholine; sodium tetrahydroborate; sodium azide; tetrapropylammonium perruthennate; TEA; tetrabutyl ammonium fluoride; water; toluene-4-sulfonic acid; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.48.310

upstream raw materials:

methanesulfonyl chloride

(1R,3R)-N-allyloxycarbonyl-1-(4-N-allyloxycarbonylaminomethyl)phenyl-3,4-O-isopropylidene-3,4-dihydroxybutylamine

4-(tert-butyldimethylsiloxymethyl)bromobenzene

(3R)-1-(4-tert-butyldimethylsiloxymethylphenyl)-3,4-O-isopropylidene-3,4-dihydroxybutanol

Downstream raw materials:

allyl (1R,5S,6S)-2-[(3S,5R)-1-allyloxycarbonyl-5-[4-(N-allyloxycarbonylaminomethyl)phenyl]pyrrolidin-3-ylthio]-6-[(R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

(2R,4S)-4-acetylthio-2-[4-(N-allyloxycarbonylaminomethyl)phenyl]-1-allyloxycarbonylpyrrolidine

(2R,4S)-2-[4-(Allyloxycarbonylamino-methyl)-phenyl]-4-mercapto-pyrrolidine-1-carboxylic acid allyl ester

(2R,4R)-2-[4-(N-allyloxycarbonylaminomethyl)phenyl]-1-allyloxycarbonyl-4-mesyloxypyrrolidine

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