5-((3R,4R,5S,9S)-3,5-bis(tert-butyldimethylsilyloxy)-4-methyl-9-(triethylsilyloxy)undecylthio)-1-phenyl-1H-tetrazole

Base Information

• Chemical Name: 5-((3R,4R,5S,9S)-3,5-bis(tert-butyldimethylsilyloxy)-4-methyl-9-(triethylsilyloxy)undecylthio)-1-phenyl-1H-tetrazole
• CAS No.: 1000694-61-0
• Molecular Formula: C₃₇H₇₂N₄O₃SSi₃
• Molecular Weight: 737.326

Synonyms:5-((3R,4R,5S,9S)-3,5-bis(tert-butyldimethylsilyloxy)-4-methyl-9-(triethylsilyloxy)undecylthio)-1-phenyl-1H-tetrazole

Chemical Property of 5-((3R,4R,5S,9S)-3,5-bis(tert-butyldimethylsilyloxy)-4-methyl-9-(triethylsilyloxy)undecylthio)-1-phenyl-1H-tetrazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-((3R,4R,5S,9S)-3,5-bis(tert-butyldimethylsilyloxy)-4-methyl-9-(triethylsilyloxy)undecylthio)-1-phenyl-1H-tetrazole

There total 14 articles about 5-((3R,4R,5S,9S)-3,5-bis(tert-butyldimethylsilyloxy)-4-methyl-9-(triethylsilyloxy)undecylthio)-1-phenyl-1H-tetrazole 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: 86.0%

(3R,4R,5S,9S)-3,5-bis(tert-butyldimethylsilyloxy)-4-methyl-9-(triethylsilyloxy)undecan-1-ol (1000694-60-9) + 1-Phenyl-1H-tetrazole-5-thiol (86-93-1) → 5-((3R,4R,5S,9S)-3,5-bis(tert-butyldimethylsilyloxy)-4-methyl-9-(triethylsilyloxy)undecylthio)-1-phenyl-1H-tetrazole (1000694-61-0)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1002/anie.201407806

Reference yield:

(4R,5S,6S,10S)-4,6-bis(tert-butyldimethylsilyloxy)-5-methyl-10-(triethylsilyloxy)dodec-1-ene (1000694-59-6) → 5-((3R,4R,5S,9S)-3,5-bis(tert-butyldimethylsilyloxy)-4-methyl-9-(triethylsilyloxy)undecylthio)-1-phenyl-1H-tetrazole (1000694-61-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tetrahydrofuran; acetone; aq. phosphate buffer / 20 °C / pH 7

2: sodium periodate / tetrahydrofuran; aq. phosphate buffer / 3 h / 20 °C / pH 7

3: sodium tetrahydroborate / ethanol / 1 h / 20 °C

4: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 1 h / 0 °C

With sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; di-isopropyl azodicarboxylate; 4-methylmorpholine N-oxide; triphenylphosphine; In tetrahydrofuran; aq. phosphate buffer; ethanol; acetone;

DOI:10.1002/anie.201407806

Reference yield:

(S)-5-hydroxy-N-methoxy-N-methylheptanamide (1000694-54-1) → 5-((3R,4R,5S,9S)-3,5-bis(tert-butyldimethylsilyloxy)-4-methyl-9-(triethylsilyloxy)undecylthio)-1-phenyl-1H-tetrazole (1000694-61-0)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 3 h / -78 °C

2.1: diisobutylaluminium hydride / hexane; toluene / 2 h / -78 °C

3.1: titanium tetrachloride / dichloromethane / 0.08 h / 0 °C

3.2: 0.33 h / 0 °C

3.3: 1 h / 0 °C

4.1: 2,6-dimethylpyridine / dichloromethane / 2 h / -78 °C

5.1: lithium borohydride / diethyl ether; methanol; tetrahydrofuran / 1.25 h / 0 - 20 °C

5.2: 0.5 h

6.1: dichloromethane / 0.17 h / 20 °C / Molecular sieve

6.2: 0.5 h / 20 °C

7.1: diethyl ether / 0.5 h / -78 °C

7.2: 20 °C

8.1: 2,6-dimethylpyridine / dichloromethane / 4 h / -78 - 20 °C

9.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tetrahydrofuran; acetone; aq. phosphate buffer / 20 °C / pH 7

10.1: sodium periodate / tetrahydrofuran; aq. phosphate buffer / 3 h / 20 °C / pH 7

11.1: sodium tetrahydroborate / ethanol / 1 h / 20 °C

12.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 1 h / 0 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; lithium borohydride; di-isopropyl azodicarboxylate; titanium tetrachloride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triphenylphosphine; In tetrahydrofuran; methanol; aq. phosphate buffer; diethyl ether; ethanol; hexane; dichloromethane; acetone; toluene;

DOI:10.1002/anie.201407806

upstream raw materials:

(3R,4R,5S,9S)-3,5-bis(tert-butyldimethylsilyloxy)-4-methyl-9-(triethylsilyloxy)undecan-1-ol

1-Phenyl-1H-tetrazole-5-thiol

(4R,5S,6S,10S)-4,6-bis(tert-butyldimethylsilyloxy)-5-methyl-10-(triethylsilyloxy)dodec-1-ene

N-methoxy-N-methyl-5-oxopentanamide

Downstream raw materials:

(3S,7S,8R,9R)-7,9-bis(tert-butyldimethylsilyloxy)-8-methyl-11-(1-phenyl-1H-tetrazol-5-ylsulfonyl)undecan-3-ol

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