Toluene-4-sulfonic acid (2R,4R)-4-allyloxycarbonylamino-4-[4-(allyloxycarbonylamino-methyl)-phenyl]-2-hydroxy-butyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (2R,4R)-4-allyloxycarbonylamino-4-[4-(allyloxycarbonylamino-methyl)-phenyl]-2-hydroxy-butyl ester
• CAS No.: 263155-22-2
• Molecular Formula: C₂₆H₃₂N₂O₈S
• Molecular Weight: 532.615

Synonyms:Toluene-4-sulfonic acid (2R,4R)-4-allyloxycarbonylamino-4-[4-(allyloxycarbonylamino-methyl)-phenyl]-2-hydroxy-butyl ester

Chemical Property of Toluene-4-sulfonic acid (2R,4R)-4-allyloxycarbonylamino-4-[4-(allyloxycarbonylamino-methyl)-phenyl]-2-hydroxy-butyl ester

Chemical Property:

Purity/Quality:

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Technology Process of Toluene-4-sulfonic acid (2R,4R)-4-allyloxycarbonylamino-4-[4-(allyloxycarbonylamino-methyl)-phenyl]-2-hydroxy-butyl ester

There total 18 articles about Toluene-4-sulfonic acid (2R,4R)-4-allyloxycarbonylamino-4-[4-(allyloxycarbonylamino-methyl)-phenyl]-2-hydroxy-butyl 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: 80.0%

p-toluenesulfonyl chloride (98-59-9) + (1R,3R)-N-allyloxycarbonyl-1-(4-N-allyloxycarbonylaminomethyl)phenyl-3,4-O-isopropylidene-3,4-dihydroxybutylamine (263155-21-1) → Toluene-4-sulfonic acid (2R,4R)-4-allyloxycarbonylamino-4-[4-(allyloxycarbonylamino-methyl)-phenyl]-2-hydroxy-butyl ester (263155-22-2)

Guidance literature:

With TEA; In dichloromethane;

DOI:10.1248/cpb.48.310

Reference yield:

4-(tert-butyldimethylsiloxymethyl)bromobenzene (87736-74-1) → Toluene-4-sulfonic acid (2R,4R)-4-allyloxycarbonylamino-4-[4-(allyloxycarbonylamino-methyl)-phenyl]-2-hydroxy-butyl ester (263155-22-2)

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: 80 percent / TEA / CH₂Cl₂

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) → Toluene-4-sulfonic acid (2R,4R)-4-allyloxycarbonylamino-4-[4-(allyloxycarbonylamino-methyl)-phenyl]-2-hydroxy-butyl ester (263155-22-2)

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: 80 percent / TEA / CH₂Cl₂

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:

p-toluenesulfonyl 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:

Toluene-4-sulfonic acid (2R,4R)-4-allyloxycarbonylamino-4-[4-(allyloxycarbonylamino-methyl)-phenyl]-2-(tert-butyl-dimethyl-silanyloxy)-butyl ester

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