<2Z,4E,6E,8E,10S,11S,12R,13R,15R,15(2S,3S,5S,7R,8R,9S)>-15-<9-(tert-butyldimethylsiloxy)-7-(2-oxoethyl)-3--4,4,8-trimethyl-1,6-dioxaspiro<4.5>dec-2-yl>-11,13-bis(tert-butyldimethylsiloxy)-15-methoxy-3,7,8,10,12-pentamethy

Base Information

• Chemical Name: <2Z,4E,6E,8E,10S,11S,12R,13R,15R,15(2S,3S,5S,7R,8R,9S)>-15-<9-(tert-butyldimethylsiloxy)-7-(2-oxoethyl)-3--4,4,8-trimethyl-1,6-dioxaspiro<4.5>dec-2-yl>-11,13-bis(tert-butyldimethylsiloxy)-15-methoxy-3,7,8,10,12-pentamethy
• CAS No.: 144467-93-6
• Molecular Formula: C₆₈H₁₁₂NO₁₃PSi₃
• Molecular Weight: 1266.87
• Mol file: 144467-93-6.mol

Synonyms:<2Z,4E,6E,8E,10S,11S,12R,13R,15R,15(2S,3S,5S,7R,8R,9S)>-15-<9-(tert-butyldimethylsiloxy)-7-(2-oxoethyl)-3--4,4,8-trimethyl-1,6-dioxaspiro<4.5>dec-2-yl>-11,13-bis(tert-butyldimethylsiloxy)-15-methoxy-3,7,8,10,12-pentamethy

Chemical Property of <2Z,4E,6E,8E,10S,11S,12R,13R,15R,15(2S,3S,5S,7R,8R,9S)>-15-<9-(tert-butyldimethylsiloxy)-7-(2-oxoethyl)-3--4,4,8-trimethyl-1,6-dioxaspiro<4.5>dec-2-yl>-11,13-bis(tert-butyldimethylsiloxy)-15-methoxy-3,7,8,10,12-pentamethy

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <2Z,4E,6E,8E,10S,11S,12R,13R,15R,15(2S,3S,5S,7R,8R,9S)>-15-<9-(tert-butyldimethylsiloxy)-7-(2-oxoethyl)-3--4,4,8-trimethyl-1,6-dioxaspiro<4.5>dec-2-yl>-11,13-bis(tert-butyldimethylsiloxy)-15-methoxy-3,7,8,10,12-pentamethy

There total 36 articles about <2Z,4E,6E,8E,10S,11S,12R,13R,15R,15(2S,3S,5S,7R,8R,9S)>-15-<9-(tert-butyldimethylsiloxy)-7-(2-oxoethyl)-3--4,4,8-trimethyl-1,6-dioxaspiro<4.5>dec-2-yl>-11,13-bis(tert-butyldimethylsiloxy)-15-methoxy-3,7,8,10,12-pentamethy 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%

<2Z,4E,6E,8E,10S,11S,12R,13R,15R,15(2S,3S,5S,7R,8R,9S)>-15-<9-(tert-butyldimethylsiloxy)-7-(2-hydroxyethyl)-3--4,4,8-trimethyl-1,6-dioxaspiro<4.5>dec-2-yl>-11,13-bis(tert-butyldimethylsiloxy)-15-methoxy-3,7,8,10,12-pentam (144467-92-5) → <2Z,4E,6E,8E,10S,11S,12R,13R,15R,15(2S,3S,5S,7R,8R,9S)>-15-<9-(tert-butyldimethylsiloxy)-7-(2-oxoethyl)-3--4,4,8-trimethyl-1,6-dioxaspiro<4.5>dec-2-yl>-11,13-bis(tert-butyldimethylsiloxy)-15-methoxy-3,7,8,10,12-pentamethy (144467-93-6)

Guidance literature:

With pyridine; Dess-Martin periodane; In dichloromethane; for 1h;

DOI:10.1021/ja00050a024

Reference yield:

3,3,4-trimethyl-4-pentenoic acid (90370-81-3) → <2Z,4E,6E,8E,10S,11S,12R,13R,15R,15(2S,3S,5S,7R,8R,9S)>-15-<9-(tert-butyldimethylsiloxy)-7-(2-oxoethyl)-3--4,4,8-trimethyl-1,6-dioxaspiro<4.5>dec-2-yl>-11,13-bis(tert-butyldimethylsiloxy)-15-methoxy-3,7,8,10,12-pentamethy (144467-93-6)

Guidance literature:

Multi-step reaction with 31 steps

1: Et₃N / diethyl ether / 1 h / 0 °C

2: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 2.) THF, hexane, a) -78 deg C, 15 min, b) 0 deg C, 30 min

3: 1.) NaHMDS, 2.) 2-(phenylsulfonyl)-3-phenyloxaziridine / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C

4: 1.) AlMe₃ / 1.) CH₂Cl₂, toluene, 25 deg C, 30 min, 2.) CH₂Cl₂, toluene, reflux, 24 h

5: 1.) NaH / 1.) DMF, THF, 15 min, 2.) DMF, THF, 5 min

6: 93 percent / DIBAL-H / toluene / -78 °C

7: 71 percent / MgBr₂*Et₂O / CH₂Cl₂ / 1 h / -20 °C

8: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

9: 1.) tris(triphenylphosphine)rhodium(I) chloride, catecholborane, 2.) 2M NaOH, 30percent aq. H₂O₂ / 1.) THF, 50 min, 2.) THF, EtOH, a) 0 deg C, 30 min, b) from 0 deg C to RT, 30 min

10: 89 percent / DMAP, pyridine / CH₂Cl₂

11: 1.) N-methylmorpholine N-oxide, OsO₄, 2.) NaIO₄ / 1.) t-BuOH, THF, H₂O, 20 h, 2.) t-BuOH, THF, H₂O, 20 h

12: 99 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

13: 80 percent / BF₃*Et₂O / CH₂Cl₂ / 8 h / -78 °C

14: 71 percent / 48percent aq. HF / acetonitrile / 3.5 h / Ambient temperature

15: 1.) 9-borabicyclononane dimer, 2.) 30percent aq. H₂O₂ / 1.) THF, irrad. 30 min, 2.) THF, MeOH, 14 h, pH = 7 (phosphate buffer)

16: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

17: 91 percent / diisobutylaluminum hydride / CH₂Cl₂; toluene / 1 h / -78 °C

18: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 15 min, 2.) CH₂Cl₂, from -60 deg C to -30 deg C, 45 min

19: 1.) TiCl₄, diisopropylethylamine / 1.) CH₂Cl₂, -20 deg C to -10 deg C, 1 h, 2.) CH₂Cl₂, from -78 deg C to -50 deg C, 1.5 h

20: 74 percent / tetramethylammonium triacetoxyborohydride, AcOH / acetonitrile / a) -25 deg C, 6 h, b) 0 deg C, 20 h

21: 72 percent / Ph₃P, di-tert-butyl azodicarboxylate / benzene / 2.5 h

22: 84 percent / LiBH₄ / tetrahydrofuran; methanol / 48 h / Ambient temperature

23: 84 percent / pyridine

24: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

25: 94 percent / H₂O, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / CH₂Cl₂ / 0.33 h

26: 98 percent / DIBAL-H / CH₂Cl₂ / -78 °C

27: 88 percent / pyridine, Dess-Martin periodinane / CH₂Cl₂ / 0.33 h

28: 2.) (MeCN)2PdCl₂ / 1.) THF, hexane, 30 min, 2.) 1-methyl-2-pyrrolidinone, 76 h

29: 1.) pyridine, phosphorus trichloride, 3.) 30percent aq. H₂O₂

30: 76 percent / pyridinium hydrofluoride / tetrahydrofuran / 8 h

31: 87 percent / pyridine, Dess-Martin periodinane / CH₂Cl₂ / 1 h

With pyridine; 2,6-dimethylpyridine; dmap; dichloro bis(acetonitrile) palladium(II); sodium hydroxide; sodium periodate; Wilkinson's catalyst; osmium(VIII) oxide; lithium borohydride; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; oxalyl dichloride; di-tert-butyl-diazodicarboxylate; boron trifluoride diethyl etherate; hydrogen fluoride; water; dihydrogen peroxide; trimethylaluminum; sodium hexamethyldisilazane; titanium tetrachloride; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; N-(benzenesulfonyl)-3-phenyloxaziridine; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; magnesium bromide; tetramethylammonium triacetoxyborohydride; phosphorus trichloride; benzo[1,3,2]dioxaborole; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; acetonitrile; benzene;

DOI:10.1021/ja00050a024

Reference yield:

(S)-2-(4-Methoxy-benzyloxy)-3,3,4-trimethyl-pent-4-enal (139426-80-5) → <2Z,4E,6E,8E,10S,11S,12R,13R,15R,15(2S,3S,5S,7R,8R,9S)>-15-<9-(tert-butyldimethylsiloxy)-7-(2-oxoethyl)-3--4,4,8-trimethyl-1,6-dioxaspiro<4.5>dec-2-yl>-11,13-bis(tert-butyldimethylsiloxy)-15-methoxy-3,7,8,10,12-pentamethy (144467-93-6)

Guidance literature:

Multi-step reaction with 25 steps

1: 71 percent / MgBr₂*Et₂O / CH₂Cl₂ / 1 h / -20 °C

2: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

3: 1.) tris(triphenylphosphine)rhodium(I) chloride, catecholborane, 2.) 2M NaOH, 30percent aq. H₂O₂ / 1.) THF, 50 min, 2.) THF, EtOH, a) 0 deg C, 30 min, b) from 0 deg C to RT, 30 min

4: 89 percent / DMAP, pyridine / CH₂Cl₂

5: 1.) N-methylmorpholine N-oxide, OsO₄, 2.) NaIO₄ / 1.) t-BuOH, THF, H₂O, 20 h, 2.) t-BuOH, THF, H₂O, 20 h

6: 99 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

7: 80 percent / BF₃*Et₂O / CH₂Cl₂ / 8 h / -78 °C

8: 71 percent / 48percent aq. HF / acetonitrile / 3.5 h / Ambient temperature

9: 1.) 9-borabicyclononane dimer, 2.) 30percent aq. H₂O₂ / 1.) THF, irrad. 30 min, 2.) THF, MeOH, 14 h, pH = 7 (phosphate buffer)

10: 98 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

11: 91 percent / diisobutylaluminum hydride / CH₂Cl₂; toluene / 1 h / -78 °C

12: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 15 min, 2.) CH₂Cl₂, from -60 deg C to -30 deg C, 45 min

13: 1.) TiCl₄, diisopropylethylamine / 1.) CH₂Cl₂, -20 deg C to -10 deg C, 1 h, 2.) CH₂Cl₂, from -78 deg C to -50 deg C, 1.5 h

14: 74 percent / tetramethylammonium triacetoxyborohydride, AcOH / acetonitrile / a) -25 deg C, 6 h, b) 0 deg C, 20 h

15: 72 percent / Ph₃P, di-tert-butyl azodicarboxylate / benzene / 2.5 h

16: 84 percent / LiBH₄ / tetrahydrofuran; methanol / 48 h / Ambient temperature

17: 84 percent / pyridine

18: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

19: 94 percent / H₂O, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / CH₂Cl₂ / 0.33 h

20: 98 percent / DIBAL-H / CH₂Cl₂ / -78 °C

21: 88 percent / pyridine, Dess-Martin periodinane / CH₂Cl₂ / 0.33 h

22: 2.) (MeCN)2PdCl₂ / 1.) THF, hexane, 30 min, 2.) 1-methyl-2-pyrrolidinone, 76 h

23: 1.) pyridine, phosphorus trichloride, 3.) 30percent aq. H₂O₂

24: 76 percent / pyridinium hydrofluoride / tetrahydrofuran / 8 h

25: 87 percent / pyridine, Dess-Martin periodinane / CH₂Cl₂ / 1 h

With pyridine; 2,6-dimethylpyridine; dmap; dichloro bis(acetonitrile) palladium(II); sodium hydroxide; sodium periodate; Wilkinson's catalyst; osmium(VIII) oxide; lithium borohydride; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; di-tert-butyl-diazodicarboxylate; boron trifluoride diethyl etherate; hydrogen fluoride; water; dihydrogen peroxide; titanium tetrachloride; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; magnesium bromide; tetramethylammonium triacetoxyborohydride; phosphorus trichloride; benzo[1,3,2]dioxaborole; In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile; benzene;

DOI:10.1021/ja00050a024

upstream raw materials:

<2Z,4E,6E,8E,10S,11S,12R,13R,15R,15(2S,3S,5S,7R,8R,9S)>-15-<9-(tert-butyldimethylsiloxy)-7-(2-hydroxyethyl)-3--4,4,8-trimethyl-1,6-dioxaspiro<4.5>dec-2-yl>-11,13-bis(tert-butyldimethylsiloxy)-15-methoxy-3,7,8,10,12-pentam

3,3,4-trimethyl-4-pentenoic acid

<2S,3R>-2-methyl-3-(triethylsiloxy)-4-pentenal

<2S>-2-hydroxy-N-methoxy-N,3,3,4-tetramethyl-4-pentenamide