Carbonic acid (E)-(S)-4-((1R,2S)-5,5-bis-benzenesulfonyl-1-methyl-2-trimethylsilanyloxy-pentyloxy)-hex-2-enyl ester methyl ester

Base Information

• Chemical Name: Carbonic acid (E)-(S)-4-((1R,2S)-5,5-bis-benzenesulfonyl-1-methyl-2-trimethylsilanyloxy-pentyloxy)-hex-2-enyl ester methyl ester
• CAS No.: 214967-16-5
• Molecular Formula: C₂₉H₄₂O₉S₂Si
• Molecular Weight: 626.865
• Mol file: 214967-16-5.mol

Synonyms:Carbonic acid (E)-(S)-4-((1R,2S)-5,5-bis-benzenesulfonyl-1-methyl-2-trimethylsilanyloxy-pentyloxy)-hex-2-enyl ester methyl ester

Chemical Property of Carbonic acid (E)-(S)-4-((1R,2S)-5,5-bis-benzenesulfonyl-1-methyl-2-trimethylsilanyloxy-pentyloxy)-hex-2-enyl ester methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Carbonic acid (E)-(S)-4-((1R,2S)-5,5-bis-benzenesulfonyl-1-methyl-2-trimethylsilanyloxy-pentyloxy)-hex-2-enyl ester methyl ester

There total 13 articles about Carbonic acid (E)-(S)-4-((1R,2S)-5,5-bis-benzenesulfonyl-1-methyl-2-trimethylsilanyloxy-pentyloxy)-hex-2-enyl ester methyl 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: 87.0%

methyl chloroformate (79-22-1) + (E)-(S)-4-((1R,2S)-5,5-Bis-benzenesulfonyl-1-methyl-2-trimethylsilanyloxy-pentyloxy)-hex-2-en-1-ol (214967-26-7) → Carbonic acid (E)-(S)-4-((1R,2S)-5,5-bis-benzenesulfonyl-1-methyl-2-trimethylsilanyloxy-pentyloxy)-hex-2-enyl ester methyl ester (214967-16-5)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃;

DOI:10.1016/S0040-4039(98)01506-8

Reference yield:

(S)-2-[(R)-1-(1-Benzyloxymethyl-propoxy)-ethyl]-oxirane (214967-07-4) → Carbonic acid (E)-(S)-4-((1R,2S)-5,5-bis-benzenesulfonyl-1-methyl-2-trimethylsilanyloxy-pentyloxy)-hex-2-enyl ester methyl ester (214967-16-5)

Guidance literature:

Multi-step reaction with 13 steps

1: 90 percent / 18-crown-6 / methanol / Ambient temperature

2: 87 percent / imidazole / dimethylformamide / 60 °C

3: 1.) DIBAH, PE, 2.) NaBH₄ / 1.) -70 deg C -> RT, 2.) i-PrOH, RT

4: PPh₃, imidazole, I₂ / acetonitrile; ethanol / 34 °C

5: 68 percent / dimethylformamide; benzene / 110 °C

6: 81 percent / BF₃*OEt₂, DMS / CH₂Cl₂ / Ambient temperature

7: 83 percent / pyridine / CH₂Cl₂ / Ambient temperature

8: NEt₃ / tetrahydrofuran / 40 °C

9: DIBAH / CH₂Cl₂ / -70 °C

10: SO₃*pyridine, DMSO, Et(i-Pr)2N / CH₂Cl₂ / 0 °C

11: t-BuOK / tetrahydrofuran / 0 °C

12: DIBAH / CH₂Cl₂ / -70 °C

13: 87 percent / pyridine / CH₂Cl₂ / 0 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; 18-crown-6 ether; pyridine-SO₃ complex; 2,3-dimercapto-succinic acid; boron trifluoride diethyl etherate; potassium tert-butylate; iodine; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1016/S0040-4039(98)01506-8

Reference yield:

(3S,4R)-4-(1-Benzyloxymethyl-propoxy)-3-hydroxy-pentanenitrile (214967-21-2) → Carbonic acid (E)-(S)-4-((1R,2S)-5,5-bis-benzenesulfonyl-1-methyl-2-trimethylsilanyloxy-pentyloxy)-hex-2-enyl ester methyl ester (214967-16-5)

Guidance literature:

Multi-step reaction with 12 steps

1: 87 percent / imidazole / dimethylformamide / 60 °C

2: 1.) DIBAH, PE, 2.) NaBH₄ / 1.) -70 deg C -> RT, 2.) i-PrOH, RT

3: PPh₃, imidazole, I₂ / acetonitrile; ethanol / 34 °C

4: 68 percent / dimethylformamide; benzene / 110 °C

5: 81 percent / BF₃*OEt₂, DMS / CH₂Cl₂ / Ambient temperature

6: 83 percent / pyridine / CH₂Cl₂ / Ambient temperature

7: NEt₃ / tetrahydrofuran / 40 °C

8: DIBAH / CH₂Cl₂ / -70 °C

9: SO₃*pyridine, DMSO, Et(i-Pr)2N / CH₂Cl₂ / 0 °C

10: t-BuOK / tetrahydrofuran / 0 °C

11: DIBAH / CH₂Cl₂ / -70 °C

12: 87 percent / pyridine / CH₂Cl₂ / 0 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; pyridine-SO₃ complex; 2,3-dimercapto-succinic acid; boron trifluoride diethyl etherate; potassium tert-butylate; iodine; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1016/S0040-4039(98)01506-8

upstream raw materials:

methyl chloroformate

(E)-(S)-4-((1R,2S)-5,5-Bis-benzenesulfonyl-1-methyl-2-trimethylsilanyloxy-pentyloxy)-hex-2-en-1-ol

(S)-2-[(R)-1-(1-Benzyloxymethyl-propoxy)-ethyl]-oxirane

(3S,4R)-4-(1-Benzyloxymethyl-propoxy)-3-hydroxy-pentanenitrile