(1S,6S,12S)-(2E,4Z,8E,10E)-1-(2-benzenesulfonylethyl)-12-(t-butyldimethylsilanoxy)-12-((E)-(2R,4S,5S,6R)-5-methyl-6-propenyl-4-(t-butyldimethylsilanoxy)-tetrahydropyran-2-yl)-4,6,8-trimethyldodeca-2,4,8,10-tetraen-1-ol

Base Information

• Chemical Name: (1S,6S,12S)-(2E,4Z,8E,10E)-1-(2-benzenesulfonylethyl)-12-(t-butyldimethylsilanoxy)-12-((E)-(2R,4S,5S,6R)-5-methyl-6-propenyl-4-(t-butyldimethylsilanoxy)-tetrahydropyran-2-yl)-4,6,8-trimethyldodeca-2,4,8,10-tetraen-1-ol
• CAS No.: 343262-99-7
• Molecular Formula: C₄₄H₇₄O₆SSi₂
• Molecular Weight: 787.305

Synonyms:(1S,6S,12S)-(2E,4Z,8E,10E)-1-(2-benzenesulfonylethyl)-12-(t-butyldimethylsilanoxy)-12-((E)-(2R,4S,5S,6R)-5-methyl-6-propenyl-4-(t-butyldimethylsilanoxy)-tetrahydropyran-2-yl)-4,6,8-trimethyldodeca-2,4,8,10-tetraen-1-ol

Chemical Property of (1S,6S,12S)-(2E,4Z,8E,10E)-1-(2-benzenesulfonylethyl)-12-(t-butyldimethylsilanoxy)-12-((E)-(2R,4S,5S,6R)-5-methyl-6-propenyl-4-(t-butyldimethylsilanoxy)-tetrahydropyran-2-yl)-4,6,8-trimethyldodeca-2,4,8,10-tetraen-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (1S,6S,12S)-(2E,4Z,8E,10E)-1-(2-benzenesulfonylethyl)-12-(t-butyldimethylsilanoxy)-12-((E)-(2R,4S,5S,6R)-5-methyl-6-propenyl-4-(t-butyldimethylsilanoxy)-tetrahydropyran-2-yl)-4,6,8-trimethyldodeca-2,4,8,10-tetraen-1-ol

There total 20 articles about (1S,6S,12S)-(2E,4Z,8E,10E)-1-(2-benzenesulfonylethyl)-12-(t-butyldimethylsilanoxy)-12-((E)-(2R,4S,5S,6R)-5-methyl-6-propenyl-4-(t-butyldimethylsilanoxy)-tetrahydropyran-2-yl)-4,6,8-trimethyldodeca-2,4,8,10-tetraen-1-ol 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: 89.0%

2,2-dimethylpropionic acid (1S,6S,12S)-(2E,4Z,8E,10E)-1-(2-benzenesulfonylethyl)-12-(t-butyldimethylsilanoxy)-12-((E)-(2R,4S,5S,6R)-5-methyl-6-propenyl-4-(t-butyldimethylsilanoxy)-tetrahydropyran-2-yl)-4,6,8-trimethyldodeca-2,4,8,10-tetraenyl ester (343262-78-2) → (1S,6S,12S)-(2E,4Z,8E,10E)-1-(2-benzenesulfonylethyl)-12-(t-butyldimethylsilanoxy)-12-((E)-(2R,4S,5S,6R)-5-methyl-6-propenyl-4-(t-butyldimethylsilanoxy)-tetrahydropyran-2-yl)-4,6,8-trimethyldodeca-2,4,8,10-tetraen-1-ol (343262-99-7)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 0.166667h;

DOI:10.1021/ol015753k

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (1S,6S,12S)-(2E,4Z,8E,10E)-1-(2-benzenesulfonylethyl)-12-(t-butyldimethylsilanoxy)-12-((E)-(2R,4S,5S,6R)-5-methyl-6-propenyl-4-(t-butyldimethylsilanoxy)-tetrahydropyran-2-yl)-4,6,8-trimethyldodeca-2,4,8,10-tetraen-1-ol (343262-99-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 91 percent / imidazole; DMAP / dimethylformamide / 16 h

2: 99 percent / DIBAL / CH₂Cl₂ / 0.17 h / -78 °C

3: 93 percent / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 1.5 h

4: 266 mg / t-BuOK; tributylphosphine / toluene; tetrahydrofuran / 0 °C

5: 89 percent / DIBAL / CH₂Cl₂ / 0.17 h / -78 °C

With 1H-imidazole; dmap; tributylphosphine; potassium tert-butylate; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 3: Dess-Martin oxidation;

DOI:10.1021/ol015753k

Reference yield:

(S)-4-Benzyl-3-((E)-(2S,3R)-3-hydroxy-2-methyl-hex-4-enoyl)-oxazolidin-2-one (251318-99-7) → (1S,6S,12S)-(2E,4Z,8E,10E)-1-(2-benzenesulfonylethyl)-12-(t-butyldimethylsilanoxy)-12-((E)-(2R,4S,5S,6R)-5-methyl-6-propenyl-4-(t-butyldimethylsilanoxy)-tetrahydropyran-2-yl)-4,6,8-trimethyldodeca-2,4,8,10-tetraen-1-ol (343262-99-7)

Guidance literature:

Multi-step reaction with 19 steps

1: 99 percent / imidazole / CH₂Cl₂ / 20 h

2: 86 percent / LiBH₄ / diethyl ether; H₂O / -20 - 5 °C

3: 98 percent / dimethylsulfoxide; oxalyl chloride; triethylamine / CH₂Cl₂ / -78 - -30 °C

4: 85 percent / diethyl ether / 3 h / -78 °C

5: 67 percent / CSA / CH₂Cl₂ / 40 h

6: 74 percent / AD-mix-α / 2-methyl-propan-2-ol; H2O / 20 h

7: 100 percent / NaIO₄ / H₂O; tetrahydrofuran / 0.5 h

8: 88 percent / CH₂Cl₂ / 1.5 h

9: 96 percent / DIBAL / CH₂Cl₂ / 0.5 h / -78 °C

10: 95 percent / TBHP; Ti(OiPr)4; diethyl-L-tartrate / CH₂Cl₂ / 0.67 h

11: 95 percent / pyridine / CH₂Cl₂ / 5 h / 20 °C

12: 82 percent / TBAF / tetrahydrofuran / 24 h / 40 °C

13: 90 percent / CSA / CH₂Cl₂ / 4 h

14: 100 percent / CAN / acetonitrile; H₂O / 0.25 h

15: 91 percent / imidazole; DMAP / dimethylformamide / 16 h

16: 99 percent / DIBAL / CH₂Cl₂ / 0.17 h / -78 °C

17: 93 percent / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 1.5 h

18: 266 mg / t-BuOK; tributylphosphine / toluene; tetrahydrofuran / 0 °C

19: 89 percent / DIBAL / CH₂Cl₂ / 0.17 h / -78 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium periodate; AD-mix-α; lithium borohydride; oxalyl dichloride; ammonium cerium(IV) nitrate; diethyl (2R,3R)-tartrate; tributylphosphine; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; 3: Swern oxidation / 8: Wittig olefination / 17: Dess-Martin oxidation;

DOI:10.1021/ol015753k

upstream raw materials:

2,2-dimethylpropionic acid (1S,6S,12S)-(2E,4Z,8E,10E)-1-(2-benzenesulfonylethyl)-12-(t-butyldimethylsilanoxy)-12-((E)-(2R,4S,5S,6R)-5-methyl-6-propenyl-4-(t-butyldimethylsilanoxy)-tetrahydropyran-2-yl)-4,6,8-trimethyldodeca-2,4,8,10-tetraenyl ester

tert-butyldimethylsilyl chloride

(S)-4-Benzyl-3-((E)-(2S,3R)-3-hydroxy-2-methyl-hex-4-enoyl)-oxazolidin-2-one

(E)-(2S,3R)-3-(tert-butyldiphenylsilanoxy)-2-methylhex-4-enal

Downstream raw materials:

(2R,3S,4S,6R)-6-[(1S,7S,12S)-(2E,4E,8Z,10E)-14-benzenesulfonyl-1-(tert-butyldimethylsilanoxy)-12-triethylsilanoxy-5,7,9-trimethyltetradeca-2,4,8,10-tetraenyl]-4-(tert-butyldimethylsilanoxy)-3-methyl-2-E-propenyltetrahydropyran

(-)-ratjadone

(6S)-4-benzenesulfonyl-6-{(5S,11S)-(1E,3Z,7E,9E)-11-(tert-butyldimethylsilanoxy)-11-[(E)-(2R,4S,5S,6R)-4-(tert-butyldimethylsilanoxy)-5-methyl-6-propenyltetrahydropyran-2-yl]-3,5,7-trimethylundeca-1,3,7,9-teraenyl}-tetrahydropyran-2-ol

(6S)-4-benzenesulfonyl-6-{(5S,11S)-(1E,3Z,7E,9E)-11-(tert-butyldimethylsilanoxy)-11-[(E)-(2R,4S,5S,6R)-4-(tert-butyldimethylsilanoxy)-5-methyl-6-propenyltetrahydropyran-2-yl]-3,5,7-trimethylundeca-1,3,7,9-teraenyl}-tetrahydropyran-2-one

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