(2S,3S,4R,5S,6R)-7-(tert-butyldiphenylsilyloxy)-3,5-<(S)-3,4-dimethoxybenzylidenedioxy>-2-methoxymethoxy-4,6-dimethyl-1-heptyl 2,2-dimethylpropanoate

Base Information

• Chemical Name: (2S,3S,4R,5S,6R)-7-(tert-butyldiphenylsilyloxy)-3,5-<(S)-3,4-dimethoxybenzylidenedioxy>-2-methoxymethoxy-4,6-dimethyl-1-heptyl 2,2-dimethylpropanoate
• CAS No.: 214060-10-3
• Molecular Formula: C₄₁H₅₈O₉Si
• Molecular Weight: 722.992

Synonyms:(2S,3S,4R,5S,6R)-7-(tert-butyldiphenylsilyloxy)-3,5-<(S)-3,4-dimethoxybenzylidenedioxy>-2-methoxymethoxy-4,6-dimethyl-1-heptyl 2,2-dimethylpropanoate

Chemical Property of (2S,3S,4R,5S,6R)-7-(tert-butyldiphenylsilyloxy)-3,5-<(S)-3,4-dimethoxybenzylidenedioxy>-2-methoxymethoxy-4,6-dimethyl-1-heptyl 2,2-dimethylpropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of (2S,3S,4R,5S,6R)-7-(tert-butyldiphenylsilyloxy)-3,5-<(S)-3,4-dimethoxybenzylidenedioxy>-2-methoxymethoxy-4,6-dimethyl-1-heptyl 2,2-dimethylpropanoate

There total 19 articles about (2S,3S,4R,5S,6R)-7-(tert-butyldiphenylsilyloxy)-3,5-<(S)-3,4-dimethoxybenzylidenedioxy>-2-methoxymethoxy-4,6-dimethyl-1-heptyl 2,2-dimethylpropanoate 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%

pivaloyl chloride (3282-30-2) + (S)-2-[(2S,4S,5R,6S)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2-(3,4-dimethoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2-methoxymethoxy-ethanol (226079-82-9) → (2S,3S,4R,5S,6R)-7-(tert-butyldiphenylsilyloxy)-3,5-<(S)-3,4-dimethoxybenzylidenedioxy>-2-methoxymethoxy-4,6-dimethyl-1-heptyl 2,2-dimethylpropanoate (214060-10-3)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 10h; Ambient temperature;

DOI:10.1248/cpb.47.308

Reference yield:

(R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropanal (91751-24-5,92817-88-4,123284-89-9,112897-04-8) → (2S,3S,4R,5S,6R)-7-(tert-butyldiphenylsilyloxy)-3,5-<(S)-3,4-dimethoxybenzylidenedioxy>-2-methoxymethoxy-4,6-dimethyl-1-heptyl 2,2-dimethylpropanoate (214060-10-3)

Guidance literature:

Multi-step reaction with 16 steps

1: 98 percent / benzene / 17 h / Ambient temperature

2: 91 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 1.5 h / -78 - -60 °C

3: 98 percent / titanium tetraisopropoxide, diethyl L-(+)-tartrate, 4 Angstroem molecular sieves, tert-butylhydroperoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 23 h / -25 °C

4: 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

5: 100 percent / dl-camphorsulfonic acid / CH₂Cl₂ / 0.25 h / Ambient temperature

6: 98 percent / DIBAH / CH₂Cl₂; hexane / 24 h / -30 °C

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

8: LiAlH₄ / tetrahydrofuran / Ambient temperature

9: 98 percent / OsO₄, N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; acetone / 21 h / Ambient temperature

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

11: benzene / 12 h / Ambient temperature

12: 95 percent / MeSO2NH2, AD-mix-α / 2-methyl-propan-2-ol; H2O / 25 h / Ambient temperature

13: 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

14: 83 percent / diisopropylethylamine / CH₂Cl₂ / 144 h / Ambient temperature

15: 89 percent / LiAlH₄ / diethyl ether / 0.08 h / Ambient temperature

16: 100 percent / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 10 h / Ambient temperature

With 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; diisobutylaluminium hydride; 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:

(4S)-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-penten-1-ol (127665-68-3) → (2S,3S,4R,5S,6R)-7-(tert-butyldiphenylsilyloxy)-3,5-<(S)-3,4-dimethoxybenzylidenedioxy>-2-methoxymethoxy-4,6-dimethyl-1-heptyl 2,2-dimethylpropanoate (214060-10-3)

Guidance literature:

Multi-step reaction with 14 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

With 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; diisobutylaluminium hydride; 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:

pivaloyl chloride

(S)-2-[(2S,4S,5R,6S)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2-(3,4-dimethoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2-methoxymethoxy-ethanol

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

(R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropanal

Downstream raw materials:

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

(2S,3S,4R,5S,6S)-6-formyl-3,5-<(S)-3,4-dimethoxybenzylidenedioxy>-2-methoxymethoxy-4-methyl-1-heptyl 2,2-dimethylpropanoate

(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

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

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