<αS(2R,4E,6S,7S),2R(S),3S>-α-<4-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-5,7-dimethylnona-4,8-dienyl>-3,4-dihydro-3-methyl-2-(1-methypropyl)-2H-pyran-2-ylethanol

Base Information

• Chemical Name: <αS(2R,4E,6S,7S),2R(S),3S>-α-<4-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-5,7-dimethylnona-4,8-dienyl>-3,4-dihydro-3-methyl-2-(1-methypropyl)-2H-pyran-2-ylethanol
• CAS No.: 131413-97-3
• Molecular Formula: C₄₅H₇₂O₄Si₂
• Molecular Weight: 733.235

Synonyms:<αS(2R,4E,6S,7S),2R(S),3S>-α-<4-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-5,7-dimethylnona-4,8-dienyl>-3,4-dihydro-3-methyl-2-(1-methypropyl)-2H-pyran-2-ylethanol

Chemical Property of <αS(2R,4E,6S,7S),2R(S),3S>-α-<4-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-5,7-dimethylnona-4,8-dienyl>-3,4-dihydro-3-methyl-2-(1-methypropyl)-2H-pyran-2-ylethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <αS(2R,4E,6S,7S),2R(S),3S>-α-<4-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-5,7-dimethylnona-4,8-dienyl>-3,4-dihydro-3-methyl-2-(1-methypropyl)-2H-pyran-2-ylethanol

There total 4 articles about <αS(2R,4E,6S,7S),2R(S),3S>-α-<4-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-5,7-dimethylnona-4,8-dienyl>-3,4-dihydro-3-methyl-2-(1-methypropyl)-2H-pyran-2-ylethanol 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:

(1E,3S,4S)-1-bromo-2,4-dimethylhexa-1,5-dien-3-ol (135419-79-3) → <αS(2R,4E,6S,7S),2R(S),3S>-α-<4-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-5,7-dimethylnona-4,8-dienyl>-3,4-dihydro-3-methyl-2-(1-methypropyl)-2H-pyran-2-ylethanol (131413-97-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / imidazole, 4-dimethylaminopyridine / dimethylformamide / 96 h / 50 °C

3: 94 percent / 4-dimethylaminopyridine, NEt₃ / dimethylformamide / 15 h / Ambient temperature

4: 1.) BuLi, 2.) BF₃*Et₂O / 1.) THF, hexane, -78 deg C, 2 min, 2.) -78 deg C, 2 h, then -78 deg C -> RT, 12 h

With 1H-imidazole; dmap; n-butyllithium; boron trifluoride diethyl etherate; triethylamine; In N,N-dimethyl-formamide;

Reference yield:

(1E,3S,4S)-1-bromo-3-(tert-butyldiphenylsilyloxy)-2,4-dimethylhexa-1,5-diene (131413-95-1) → <αS(2R,4E,6S,7S),2R(S),3S>-α-<4-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-5,7-dimethylnona-4,8-dienyl>-3,4-dihydro-3-methyl-2-(1-methypropyl)-2H-pyran-2-ylethanol (131413-97-3)

Guidance literature:

Multi-step reaction with 3 steps

2: 94 percent / 4-dimethylaminopyridine, NEt₃ / dimethylformamide / 15 h / Ambient temperature

3: 1.) BuLi, 2.) BF₃*Et₂O / 1.) THF, hexane, -78 deg C, 2 min, 2.) -78 deg C, 2 h, then -78 deg C -> RT, 12 h

With dmap; n-butyllithium; boron trifluoride diethyl etherate; triethylamine; In N,N-dimethyl-formamide;

Reference yield:

<αR(2E,4S,5S)>-α-<4-(tert-butyldiphenylsilyloxy)-3,5-dimethylhepta-2,6-dienyl>oxiran-2-ylethanol → <αS(2R,4E,6S,7S),2R(S),3S>-α-<4-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-5,7-dimethylnona-4,8-dienyl>-3,4-dihydro-3-methyl-2-(1-methypropyl)-2H-pyran-2-ylethanol (131413-97-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / 4-dimethylaminopyridine, NEt₃ / dimethylformamide / 15 h / Ambient temperature

2: 1.) BuLi, 2.) BF₃*Et₂O / 1.) THF, hexane, -78 deg C, 2 min, 2.) -78 deg C, 2 h, then -78 deg C -> RT, 12 h

With dmap; n-butyllithium; boron trifluoride diethyl etherate; triethylamine; In N,N-dimethyl-formamide;

upstream raw materials:

<2S(2R,4E,6S,7S)>-2-<2-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-5,7-dimethylnona-4,8-dienyl>oxirane

(1E,3S,4S)-1-bromo-2,4-dimethylhexa-1,5-dien-3-ol

(1E,3S,4S)-1-bromo-3-(tert-butyldiphenylsilyloxy)-2,4-dimethylhexa-1,5-diene

Downstream raw materials:

(4R)-5-dehydroxy-3,4-dihydro-5-oxo-4-(phenylselenyl)-7,13-di-O-(trimethylsilyl)avermectin B₁a aglycone

(4S)-5-dehydroxy-3,4-dihydro-5-oxo-4-(phenylselenyl)-7,13-di-O-(trimethylsilyl)avermectin B₁a aglycone

(3E<2E,4S,5S,6E,8<2R,4S,6S,8R(S),9S>>,3aS,4S,7R,7aR)-7-(tert-butyldimethylsilyloxy)-3-<5-(tert-butyldimethylsilyloxy)-8-undec-10-en-2-yl>-4,6-dimethylocta-2,6-dienylidene>-4-...

(4S)-5-dehydroxy-3,4-dihydro-5-oxo-4-(phenylselenyl)-avermectin B₁a aglycone

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