Toluene-4-sulfonic acid (1R,2R,4S)-2-azido-4-(tert-butyl-dimethyl-silanyloxymethyl)-cyclopentyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (1R,2R,4S)-2-azido-4-(tert-butyl-dimethyl-silanyloxymethyl)-cyclopentyl ester
• CAS No.: 233588-79-9
• Molecular Formula: C₁₉H₃₁N₃O₄SSi
• Molecular Weight: 425.624
• Mol file: 233588-79-9.mol

Synonyms:Toluene-4-sulfonic acid (1R,2R,4S)-2-azido-4-(tert-butyl-dimethyl-silanyloxymethyl)-cyclopentyl ester

Chemical Property of Toluene-4-sulfonic acid (1R,2R,4S)-2-azido-4-(tert-butyl-dimethyl-silanyloxymethyl)-cyclopentyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (1R,2R,4S)-2-azido-4-(tert-butyl-dimethyl-silanyloxymethyl)-cyclopentyl ester

There total 9 articles about Toluene-4-sulfonic acid (1R,2R,4S)-2-azido-4-(tert-butyl-dimethyl-silanyloxymethyl)-cyclopentyl 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:

ethyl 3-cyclopentene-1-carboxylate (21622-01-5) → Toluene-4-sulfonic acid (1R,2R,4S)-2-azido-4-(tert-butyl-dimethyl-silanyloxymethyl)-cyclopentyl ester (233588-79-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 70.5 percent / MCPBA / CH₂Cl₂ / 4 h / Ambient temperature

2: 97 percent / LiAlH₄ / tetrahydrofuran / 4.5 h / -78 °C

3: 14.28 g / imidazole / CH₂Cl₂

4: (S,S)-Cr(NH₂)C₆H₁₀(NCHC₆H₂(t-Bu)2O)2 / diethyl ether / 24 h / Ambient temperature; other reagent

5: (1S)-(+)-10-camphorsulfonic acid / methanol

6: 19.62 g / CH₂Cl₂ / Ambient temperature

With 1H-imidazole; lithium aluminium tetrahydride; (S,S)-Cr(NH₂)C₆H₁₀(NCHC₆H₂(t-Bu)2O)2; (+)-10-camphorsulfonic acid; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1021/jo961241l

Reference yield:

diallylmalonic acid diethyl ester (3195-24-2) → Toluene-4-sulfonic acid (1R,2R,4S)-2-azido-4-(tert-butyl-dimethyl-silanyloxymethyl)-cyclopentyl ester (233588-79-9)

Guidance literature:

Multi-step reaction with 8 steps

1: NaCN / dimethylsulfoxide / 83 h

2: 85 percent / Et₄Pb, WOCl₂(OC₆Br₂H₃)2 / toluene / 1.5 h / 90 °C

3: 70.5 percent / MCPBA / CH₂Cl₂ / 4 h / Ambient temperature

4: 97 percent / LiAlH₄ / tetrahydrofuran / 4.5 h / -78 °C

5: 14.28 g / imidazole / CH₂Cl₂

6: (S,S)-Cr(NH₂)C₆H₁₀(NCHC₆H₂(t-Bu)2O)2 / diethyl ether / 24 h / Ambient temperature; other reagent

7: (1S)-(+)-10-camphorsulfonic acid / methanol

8: 19.62 g / CH₂Cl₂ / Ambient temperature

With 1H-imidazole; lithium aluminium tetrahydride; (S,S)-Cr(NH₂)C₆H₁₀(NCHC₆H₂(t-Bu)2O)2; WOCl₂(OC₆Br₂H₃)2; sodium cyanide; tetraethyllead(IV); (+)-10-camphorsulfonic acid; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; toluene;

DOI:10.1021/jo961241l

Reference yield:

4-ethoxycarbonyl-1,6-heptadiene (18325-74-1) → Toluene-4-sulfonic acid (1R,2R,4S)-2-azido-4-(tert-butyl-dimethyl-silanyloxymethyl)-cyclopentyl ester (233588-79-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 85 percent / Et₄Pb, WOCl₂(OC₆Br₂H₃)2 / toluene / 1.5 h / 90 °C

2: 70.5 percent / MCPBA / CH₂Cl₂ / 4 h / Ambient temperature

3: 97 percent / LiAlH₄ / tetrahydrofuran / 4.5 h / -78 °C

4: 14.28 g / imidazole / CH₂Cl₂

5: (S,S)-Cr(NH₂)C₆H₁₀(NCHC₆H₂(t-Bu)2O)2 / diethyl ether / 24 h / Ambient temperature; other reagent

6: (1S)-(+)-10-camphorsulfonic acid / methanol

7: 19.62 g / CH₂Cl₂ / Ambient temperature

With 1H-imidazole; lithium aluminium tetrahydride; (S,S)-Cr(NH₂)C₆H₁₀(NCHC₆H₂(t-Bu)2O)2; WOCl₂(OC₆Br₂H₃)2; tetraethyllead(IV); (+)-10-camphorsulfonic acid; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;

DOI:10.1021/jo961241l

upstream raw materials:

p-toluenesulfonyl chloride

4-ethoxycarbonyl-1,6-heptadiene

diallylmalonic acid diethyl ester

ethyl 3-cyclopentene-1-carboxylate