(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

Base Information

• Chemical Name: (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
• CAS No.: 226080-01-9
• Molecular Formula: C₂₉H₄₈O₁₀
• Molecular Weight: 556.694
• Mol file: 226080-01-9.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 25 articles about (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 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: 100.0%

methyllithium (917-54-4) + 2,2-Dimethyl-propionic acid (S)-2-[(2S,4S,5R,6S)-2-(3,4-dimethoxy-phenyl)-6-((E)-(1S,2R,5S)-2-methoxymethoxy-1,3,5-trimethyl-6-oxo-hex-3-enyl)-5-methyl-[1,3]dioxan-4-yl]-2-methoxymethoxy-ethyl ester (226080-00-8) → (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 (226080-01-9)

Guidance literature:

In diethyl ether; at -78 - 0 ℃; for 4h;

DOI:10.1248/cpb.47.308

Reference yield:

(4S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-penten-1-ol (127665-68-3) → (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 (226080-01-9)

Guidance literature:

Multi-step reaction with 21 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

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; 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) → (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 (226080-01-9)

Guidance literature:

Multi-step reaction with 22 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

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; 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

upstream raw materials:

methyllithium

2,2-Dimethyl-propionic acid (S)-2-[(2S,4S,5R,6S)-2-(3,4-dimethoxy-phenyl)-6-((E)-(1S,2R,5S)-2-methoxymethoxy-1,3,5-trimethyl-6-oxo-hex-3-enyl)-5-methyl-[1,3]dioxan-4-yl]-2-methoxymethoxy-ethyl ester

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

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

Downstream raw materials:

(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

(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