(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-...

Base Information

• Chemical Name: (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-...
• CAS No.: 131441-49-1
• Molecular Formula: C₆₈H₁₁₄O₈Si₄
• Molecular Weight: 1171.99

Synonyms:

Chemical Property of (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-...

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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-...

There total 34 articles about (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-... 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: 34.0%

C74H120O11SSi4 → (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-... (131441-49-1,135502-92-0)

Guidance literature:

With disodium hydrogenphosphate; sodium amalgam; In tetrahydrofuran; methanol; at -40 ℃; for 2h;

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (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-... (131441-49-1,135502-92-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 86 percent / NEt₃ / CH₂Cl₂ / 0.25 h / Ambient temperature

2: 1.) DMSO, oxalyl chloride, 2.) NEt₃ / 1.) THF, -35 deg C, 20 min, 2.) -78 deg C -> RT

3: 79 percent / NaBH₄ / methanol / Ambient temperature

4: 1.) borane methyl sulphide complex, 2.) H₂O₂, NaOH / 1.) THF, RT, 64 h, 2.) 0 deg C -> RT

5: 84 percent / toluene-p-sulphonyl chloride, pyridine / 14 h / Ambient temperature

6: 1.) tert-BuLi / 1.) hexane, THF, -78 deg C, 10 min, 2.) -78 deg C, 10 min

7: 93 percent / 80percent m-chloroperbenzoic acid (mCPBA) / CH₂Cl₂ / 0.25 h / Ambient temperature

8: 80 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / acetonitrile / 3.5 h / Ambient temperature

9: 1.) tert-BuLi / 1.) pentane, THF, -78 deg C, 10 min, 2.) -78 deg C, 1 h

10: 34 percent / 6percent Na/Hg, Na₂HPO₄ / tetrahydrofuran; methanol / 2 h / -40 °C

With pyridine; sodium hydroxide; sodium tetrahydroborate; disodium hydrogenphosphate; sodium amalgam; oxalyl dichloride; dimethylsulfide borane complex; dihydrogen peroxide; tert.-butyl lithium; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; p-toluenesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;

Reference yield:

(1S,2S,3S,5S,6S)-3-<(tert-butyldiphenylsilyloxy)methyl>-5-methyl-2-<1-methylene-3-(phenylthio)propyl>-7-oxabicyclo<4.1.0>heptan-2-ol (131414-04-5) → (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-... (131441-49-1,135502-92-0)

Guidance literature:

Multi-step reaction with 13 steps

1: 88 percent / oxone, pH 4 aqueous buffer / tetrahydrofuran; methanol / 3.5 h / Ambient temperature

2: 80 percent / 15percent aq. H₂SO₄ / tetrahydrofuran / 12 h / 60 °C

3: 91 percent / imidazole / dimethylformamide / 1 h / Ambient temperature

4: 86 percent / NEt₃ / CH₂Cl₂ / 0.25 h / Ambient temperature

5: 1.) DMSO, oxalyl chloride, 2.) NEt₃ / 1.) THF, -35 deg C, 20 min, 2.) -78 deg C -> RT

6: 79 percent / NaBH₄ / methanol / Ambient temperature

7: 1.) borane methyl sulphide complex, 2.) H₂O₂, NaOH / 1.) THF, RT, 64 h, 2.) 0 deg C -> RT

8: 84 percent / toluene-p-sulphonyl chloride, pyridine / 14 h / Ambient temperature

9: 1.) tert-BuLi / 1.) hexane, THF, -78 deg C, 10 min, 2.) -78 deg C, 10 min

10: 93 percent / 80percent m-chloroperbenzoic acid (mCPBA) / CH₂Cl₂ / 0.25 h / Ambient temperature

11: 80 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / acetonitrile / 3.5 h / Ambient temperature

12: 1.) tert-BuLi / 1.) pentane, THF, -78 deg C, 10 min, 2.) -78 deg C, 1 h

13: 34 percent / 6percent Na/Hg, Na₂HPO₄ / tetrahydrofuran; methanol / 2 h / -40 °C

With pyridine; 1H-imidazole; Oxone; sodium hydroxide; sodium tetrahydroborate; disodium hydrogenphosphate; sodium amalgam; oxalyl dichloride; dimethylsulfide borane complex; pH 4 aqueous buffer; sulfuric acid; dihydrogen peroxide; tert.-butyl lithium; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; p-toluenesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

upstream raw materials:

t-butyldimethylsiyl triflate

(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

<2R(2E,4S,5S),4S,6S,8R(S),9S>-2-<4-hydroxy-3,5-dimethylhepta-2,6-dienyl>-9-methyl-8-(1-methypropyl)-1,7-dioxaspiro<5.5>undec-10-en-4-ol

Downstream raw materials:

avermectin B₁a

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

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

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

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