(E)-(3S,6R,7S)-7-[(2S,4S,5R,6S)-2-(3,4-Dimethoxy-phenyl)-6-((S)-1-methoxymethoxy-2-triethylsilanyloxy-ethyl)-5-methyl-[1,3]dioxan-4-yl]-6-methoxymethoxy-3,5-dimethyl-oct-4-en-2-ol

Base Information

• Chemical Name: (E)-(3S,6R,7S)-7-[(2S,4S,5R,6S)-2-(3,4-Dimethoxy-phenyl)-6-((S)-1-methoxymethoxy-2-triethylsilanyloxy-ethyl)-5-methyl-[1,3]dioxan-4-yl]-6-methoxymethoxy-3,5-dimethyl-oct-4-en-2-ol
• CAS No.: 226080-03-1
• Molecular Formula: C₃₅H₆₂O₁₀Si
• Molecular Weight: 670.957

Synonyms:(E)-(3S,6R,7S)-7-[(2S,4S,5R,6S)-2-(3,4-Dimethoxy-phenyl)-6-((S)-1-methoxymethoxy-2-triethylsilanyloxy-ethyl)-5-methyl-[1,3]dioxan-4-yl]-6-methoxymethoxy-3,5-dimethyl-oct-4-en-2-ol

Chemical Property of (E)-(3S,6R,7S)-7-[(2S,4S,5R,6S)-2-(3,4-Dimethoxy-phenyl)-6-((S)-1-methoxymethoxy-2-triethylsilanyloxy-ethyl)-5-methyl-[1,3]dioxan-4-yl]-6-methoxymethoxy-3,5-dimethyl-oct-4-en-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(3S,6R,7S)-7-[(2S,4S,5R,6S)-2-(3,4-Dimethoxy-phenyl)-6-((S)-1-methoxymethoxy-2-triethylsilanyloxy-ethyl)-5-methyl-[1,3]dioxan-4-yl]-6-methoxymethoxy-3,5-dimethyl-oct-4-en-2-ol

There total 26 articles about (E)-(3S,6R,7S)-7-[(2S,4S,5R,6S)-2-(3,4-Dimethoxy-phenyl)-6-((S)-1-methoxymethoxy-2-triethylsilanyloxy-ethyl)-5-methyl-[1,3]dioxan-4-yl]-6-methoxymethoxy-3,5-dimethyl-oct-4-en-2-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:

(4S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-penten-1-ol (127665-68-3) → (E)-(3S,6R,7S)-7-[(2S,4S,5R,6S)-2-(3,4-Dimethoxy-phenyl)-6-((S)-1-methoxymethoxy-2-triethylsilanyloxy-ethyl)-5-methyl-[1,3]dioxan-4-yl]-6-methoxymethoxy-3,5-dimethyl-oct-4-en-2-ol (226080-03-1)

Guidance literature:

Multi-step reaction with 22 steps

1: 98 percent / titanium tetraisopropoxide, diethyl L-(+)-tartrate, 4 Angstroem molecular sieves, tert-butylhydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 23 h / -25 °C

2: 1.) CuCN / 1.) THF, Et₂O, -30 deg C, 30 min, 2.) THF, Et₂O, a) from -35 deg C to RT, 2 h, b) RT, 12 h

3: 100 percent / dl-camphorsulfonic acid / CH₂Cl₂ / 0.25 h / Ambient temperature

4: 98 percent / DIBAH / CH₂Cl₂; hexane / 24 h / -30 °C

5: Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 3 h / Ambient temperature

6: LiAlH₄ / tetrahydrofuran / Ambient temperature

7: 98 percent / OsO₄, N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; acetone / 21 h / Ambient temperature

8: aq. NaIO₄ / methanol / 6 h / Ambient temperature

9: benzene / 12 h / Ambient temperature

10: 95 percent / MeSO2NH2, AD-mix-α / 2-methyl-propan-2-ol; H2O / 25 h / Ambient temperature

11: 1.) molecular sieves 3 Angstroem, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, 2.) molecular sieves 3 Angstroem, dl-camphorsulfonic acid / 1.) CH₂Cl₂, RT, 10 min, 2.) THF, RT, 30 min

12: 83 percent / diisopropylethylamine / CH₂Cl₂ / 144 h / Ambient temperature

13: 89 percent / LiAlH₄ / diethyl ether / 0.08 h / Ambient temperature

14: 100 percent / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 10 h / Ambient temperature

15: 97 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 8 h / 0 °C

16: 100 percent / Dess-Martin reagent, pyridine / CH₂Cl₂ / 2 h / Ambient temperature

17: 1.) tert-BuLi / 1.) Et₂O, n-pentane, a) -78 deg C, 1 h, b) RT, 1 h, 2.) Et₂O, n-pentane, from -78 deg C to -25 deg C, 14 h

18: 100 percent / diisopropylethylamine / CH₂Cl₂ / 120 h / Ambient temperature

19: 77 percent / AcOH, TBAF / tetrahydrofuran / 96 h / Ambient temperature

20: 82 percent / Dess-Martin reagent, pyridine / CH₂Cl₂ / 1.5 h / Ambient temperature

21: 100 percent / diethyl ether / 4 h / -78 - 0 °C

22: 1.) tert-BuOK / 1.) THF, -78 deg C, 15 min, 2.) THF, -78 deg C, 30 min

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium periodate; AD-mix-α; osmium(VIII) oxide; lithium aluminium tetrahydride; diethyl (2R,3R)-tartrate; methanesulfonamide; 3 A molecular sieve; 4 A molecular sieve; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; tert.-butyl lithium; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; water; acetone; tert-butyl alcohol; benzene;

DOI:10.1248/cpb.47.308

Reference yield:

methyl (2E,4S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-pentenoate (226079-73-8) → (E)-(3S,6R,7S)-7-[(2S,4S,5R,6S)-2-(3,4-Dimethoxy-phenyl)-6-((S)-1-methoxymethoxy-2-triethylsilanyloxy-ethyl)-5-methyl-[1,3]dioxan-4-yl]-6-methoxymethoxy-3,5-dimethyl-oct-4-en-2-ol (226080-03-1)

Guidance literature:

Multi-step reaction with 23 steps

1: 91 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 1.5 h / -78 - -60 °C

2: 98 percent / titanium tetraisopropoxide, diethyl L-(+)-tartrate, 4 Angstroem molecular sieves, tert-butylhydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 23 h / -25 °C

3: 1.) CuCN / 1.) THF, Et₂O, -30 deg C, 30 min, 2.) THF, Et₂O, a) from -35 deg C to RT, 2 h, b) RT, 12 h

4: 100 percent / dl-camphorsulfonic acid / CH₂Cl₂ / 0.25 h / Ambient temperature

5: 98 percent / DIBAH / CH₂Cl₂; hexane / 24 h / -30 °C

6: Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 3 h / Ambient temperature

7: LiAlH₄ / tetrahydrofuran / Ambient temperature

8: 98 percent / OsO₄, N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; acetone / 21 h / Ambient temperature

9: aq. NaIO₄ / methanol / 6 h / Ambient temperature

10: benzene / 12 h / Ambient temperature

11: 95 percent / MeSO2NH2, AD-mix-α / 2-methyl-propan-2-ol; H2O / 25 h / Ambient temperature

12: 1.) molecular sieves 3 Angstroem, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, 2.) molecular sieves 3 Angstroem, dl-camphorsulfonic acid / 1.) CH₂Cl₂, RT, 10 min, 2.) THF, RT, 30 min

13: 83 percent / diisopropylethylamine / CH₂Cl₂ / 144 h / Ambient temperature

14: 89 percent / LiAlH₄ / diethyl ether / 0.08 h / Ambient temperature

15: 100 percent / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 10 h / Ambient temperature

16: 97 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 8 h / 0 °C

17: 100 percent / Dess-Martin reagent, pyridine / CH₂Cl₂ / 2 h / Ambient temperature

18: 1.) tert-BuLi / 1.) Et₂O, n-pentane, a) -78 deg C, 1 h, b) RT, 1 h, 2.) Et₂O, n-pentane, from -78 deg C to -25 deg C, 14 h

19: 100 percent / diisopropylethylamine / CH₂Cl₂ / 120 h / Ambient temperature

20: 77 percent / AcOH, TBAF / tetrahydrofuran / 96 h / Ambient temperature

21: 82 percent / Dess-Martin reagent, pyridine / CH₂Cl₂ / 1.5 h / Ambient temperature

22: 100 percent / diethyl ether / 4 h / -78 - 0 °C

23: 1.) tert-BuOK / 1.) THF, -78 deg C, 15 min, 2.) THF, -78 deg C, 30 min

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium periodate; AD-mix-α; osmium(VIII) oxide; lithium aluminium tetrahydride; diethyl (2R,3R)-tartrate; methanesulfonamide; 3 A molecular sieve; 4 A molecular sieve; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; tert.-butyl lithium; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; water; acetone; tert-butyl alcohol; benzene;

DOI:10.1248/cpb.47.308

Reference yield:

(2R,3S,4R)-5-(tert-Butyl-diphenyl-silanyloxy)-3-(3,4-dimethoxy-benzyloxy)-2,4-dimethyl-pentanal (226079-79-4) → (E)-(3S,6R,7S)-7-[(2S,4S,5R,6S)-2-(3,4-Dimethoxy-phenyl)-6-((S)-1-methoxymethoxy-2-triethylsilanyloxy-ethyl)-5-methyl-[1,3]dioxan-4-yl]-6-methoxymethoxy-3,5-dimethyl-oct-4-en-2-ol (226080-03-1)

Guidance literature:

Multi-step reaction with 14 steps

1: benzene / 12 h / Ambient temperature

2: 95 percent / MeSO2NH2, AD-mix-α / 2-methyl-propan-2-ol; H2O / 25 h / Ambient temperature

3: 1.) molecular sieves 3 Angstroem, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, 2.) molecular sieves 3 Angstroem, dl-camphorsulfonic acid / 1.) CH₂Cl₂, RT, 10 min, 2.) THF, RT, 30 min

4: 83 percent / diisopropylethylamine / CH₂Cl₂ / 144 h / Ambient temperature

5: 89 percent / LiAlH₄ / diethyl ether / 0.08 h / Ambient temperature

6: 100 percent / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 10 h / Ambient temperature

7: 97 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 8 h / 0 °C

8: 100 percent / Dess-Martin reagent, pyridine / CH₂Cl₂ / 2 h / Ambient temperature

9: 1.) tert-BuLi / 1.) Et₂O, n-pentane, a) -78 deg C, 1 h, b) RT, 1 h, 2.) Et₂O, n-pentane, from -78 deg C to -25 deg C, 14 h

10: 100 percent / diisopropylethylamine / CH₂Cl₂ / 120 h / Ambient temperature

11: 77 percent / AcOH, TBAF / tetrahydrofuran / 96 h / Ambient temperature

12: 82 percent / Dess-Martin reagent, pyridine / CH₂Cl₂ / 1.5 h / Ambient temperature

13: 100 percent / diethyl ether / 4 h / -78 - 0 °C

14: 1.) tert-BuOK / 1.) THF, -78 deg C, 15 min, 2.) THF, -78 deg C, 30 min

With pyridine; dmap; AD-mix-α; lithium aluminium tetrahydride; methanesulfonamide; 3 A molecular sieve; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; tert.-butyl lithium; Dess-Martin periodane; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; dichloromethane; water; tert-butyl alcohol; benzene;

DOI:10.1248/cpb.47.308

upstream raw materials:

triethylsilyl chloride

(2S,3S,4R,5S,6S,7R,8E,10S,11RS)-3,5-<(S)-3,4-dimethoxybenzylidenedioxy>-2,7-bis(methoxymethoxy)-4,6,8,10-tetramethyl-8-dodecene-1,11-diol

(4S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-penten-1-ol

methyl (2E,4S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-pentenoate

Downstream raw materials:

(3S,4E,6R,7S,8S,9R,10S,11S)-12-triethylsilyloxy-8,10-<(S)-3,4-dimethoxybenzylidenedioxy>-6,11-bis(methoxymethoxy)-3,5,7,9-tetramethyl-4-dodecen-2-one

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