methyl <2R-(2R*,3S*,4S*,6R*,7(RS)*,8E,10R*,11R*)>-11-(benzoyloxy)-3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-7-hydroxy-2,4,6,10-tetramethyl-8-tridecenoate

Base Information

• Chemical Name: methyl <2R-(2R*,3S*,4S*,6R*,7(RS)*,8E,10R*,11R*)>-11-(benzoyloxy)-3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-7-hydroxy-2,4,6,10-tetramethyl-8-tridecenoate
• CAS No.: 85098-27-7
• Molecular Formula: C₃₁H₅₂O₆Si
• Molecular Weight: 548.836

Synonyms:

Chemical Property of methyl <2R-(2R*,3S*,4S*,6R*,7(RS)*,8E,10R*,11R*)>-11-(benzoyloxy)-3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-7-hydroxy-2,4,6,10-tetramethyl-8-tridecenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl <2R-(2R*,3S*,4S*,6R*,7(RS)*,8E,10R*,11R*)>-11-(benzoyloxy)-3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-7-hydroxy-2,4,6,10-tetramethyl-8-tridecenoate

There total 29 articles about methyl <2R-(2R*,3S*,4S*,6R*,7(RS)*,8E,10R*,11R*)>-11-(benzoyloxy)-3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-7-hydroxy-2,4,6,10-tetramethyl-8-tridecenoate 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: 83.0%

methyl <2R-(2R*,3S*,4S*,6R*,8E,10R*,11R*)>-11-(benzoyloxy)-3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2,4,6,10-tetramethyl-7-oxo-8-tridecenoate (85098-26-6) → methyl <2R-(2R*,3S*,4S*,6R*,7(RS)*,8E,10R*,11R*)>-11-(benzoyloxy)-3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-7-hydroxy-2,4,6,10-tetramethyl-8-tridecenoate (85098-27-7,85165-48-6)

Guidance literature:

With zinc(II) tetrahydroborate; In 1,2-dimethoxyethane; Further byproducts given. Title compound not separated from byproducts; 1.) 0 deg C, 5 h, 2.) 0 deg C to room temp. 3.5 h;

DOI:10.1021/jo00156a032

Reference yield:

4-penten-3-one (1629-58-9) → methyl <2R-(2R*,3S*,4S*,6R*,7(RS)*,8E,10R*,11R*)>-11-(benzoyloxy)-3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-7-hydroxy-2,4,6,10-tetramethyl-8-tridecenoate (85098-27-7,85165-48-6)

Guidance literature:

Multi-step reaction with 14 steps

1: 19.5 percent / N(Et)3 / benzene / 2 h / 85 °C

2: 88 percent / tetrahydrofuran / 1.) -78 deg C, 5 min, 2.) room temp., 2 h

3: 16 percent / H₂ / PtO₂ / pentane / 0.5 h / Ambient temperature

4: 88 percent / BH₃ / tetrahydrofuran / 15 h / 0 °C

5: 92 percent / 1.) (COCl)2, 2.) Et₃N / CH₂Cl₂; dimethylsulfoxide / 1.) -60 deg C, 15 min, 2.) room temp., 15 min

6: 88 percent / tetrahydrofuran / 1.) -78 deg C, 5 min, 2.) room temp., 2 h

7: 65 percent / H₂ / PtO₂ / pentane / 0.5 h / Ambient temperature

8: 100 percent / p-TsOH*H₂O / CH₂Cl₂ / 0.17 h / Ambient temperature

9: 80 percent / BF₃*Et₂O / 6 h / -40 °C

10: 93 percent / pyridine / CH₂Cl₂ / 3 h / Ambient temperature

11: 89 percent / imidazole / dimethylformamide / 21 h / 85 °C

12: 93 percent / CaCO₃, HgCl₂ / acetonitrile; H₂O / 11 h / Ambient temperature

13: 1.) lithium diisopropylamide, trimethylchlorosilane, Et₃N, 2.) Pd(II)(OAc)2 / 1.) THF, HMPA, -78 deg C, 10 min, 2.) acetonitrile, 3.5 h

14: 83 percent / Zn(BH₄)2 / 1,2-dimethoxy-ethane / 1.) 0 deg C, 5 h, 2.) 0 deg C to room temp. 3.5 h

With pyridine; 1H-imidazole; palladium diacetate; chloro-trimethyl-silane; zinc(II) tetrahydroborate; oxalyl dichloride; boron trifluoride diethyl etherate; borane; hydrogen; toluene-4-sulfonic acid; triethylamine; calcium carbonate; mercury dichloride; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; pentane; benzene;

DOI:10.1021/jo00156a032

Reference yield:

methyl <2S-<2α(S*),3ξ,6β>>-6-(hydroxymethyl)-α,3-dimethyl-5-oxotetrahydro-2H-pyran-2-acetate (85098-09-5,85098-10-8) → methyl <2R-(2R*,3S*,4S*,6R*,7(RS)*,8E,10R*,11R*)>-11-(benzoyloxy)-3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-7-hydroxy-2,4,6,10-tetramethyl-8-tridecenoate (85098-27-7,85165-48-6)

Guidance literature:

Multi-step reaction with 15 steps

1: 100 percent / pyridine / CH₂Cl₂ / 0.5 h / 0 °C

2: 19.5 percent / N(Et)3 / benzene / 2 h / 85 °C

3: 88 percent / tetrahydrofuran / 1.) -78 deg C, 5 min, 2.) room temp., 2 h

4: 16 percent / H₂ / PtO₂ / pentane / 0.5 h / Ambient temperature

5: 88 percent / BH₃ / tetrahydrofuran / 15 h / 0 °C

6: 92 percent / 1.) (COCl)2, 2.) Et₃N / CH₂Cl₂; dimethylsulfoxide / 1.) -60 deg C, 15 min, 2.) room temp., 15 min

7: 88 percent / tetrahydrofuran / 1.) -78 deg C, 5 min, 2.) room temp., 2 h

8: 65 percent / H₂ / PtO₂ / pentane / 0.5 h / Ambient temperature

9: 100 percent / p-TsOH*H₂O / CH₂Cl₂ / 0.17 h / Ambient temperature

10: 80 percent / BF₃*Et₂O / 6 h / -40 °C

11: 93 percent / pyridine / CH₂Cl₂ / 3 h / Ambient temperature

12: 89 percent / imidazole / dimethylformamide / 21 h / 85 °C

13: 93 percent / CaCO₃, HgCl₂ / acetonitrile; H₂O / 11 h / Ambient temperature

14: 1.) lithium diisopropylamide, trimethylchlorosilane, Et₃N, 2.) Pd(II)(OAc)2 / 1.) THF, HMPA, -78 deg C, 10 min, 2.) acetonitrile, 3.5 h

15: 83 percent / Zn(BH₄)2 / 1,2-dimethoxy-ethane / 1.) 0 deg C, 5 h, 2.) 0 deg C to room temp. 3.5 h

With pyridine; 1H-imidazole; palladium diacetate; chloro-trimethyl-silane; zinc(II) tetrahydroborate; oxalyl dichloride; boron trifluoride diethyl etherate; borane; hydrogen; toluene-4-sulfonic acid; triethylamine; calcium carbonate; mercury dichloride; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; pentane; benzene;

DOI:10.1021/jo00156a032

upstream raw materials:

methyl <2R-(2R*,3S*,4S*,6R*,8E,10R*,11R*)>-11-(benzoyloxy)-3-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-2,4,6,10-tetramethyl-7-oxo-8-tridecenoate

4-penten-3-one

(2R,3S,4S,6R)-3-Hydroxy-6-[2-((3R,4R)-4-hydroxy-3-methyl-hexyl)-[1,3]dithiolan-2-yl]-2,4-dimethyl-heptanoic acid methyl ester

Benzoic acid (1R,2R)-1-ethyl-4-[2-((1R,3S,4S,5R)-4-hydroxy-5-methoxycarbonyl-1,3-dimethyl-hexyl)-[1,3]dithiolan-2-yl]-2-methyl-butyl ester

Downstream raw materials:

10-deoxymethynolide

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