(2S,3R,5S,8R,9S,10R,12S)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-8,9-dihydroxy-3-(4-methoxy-benzyloxy)-2,3,10-trimethyl-12-triisopropylsilanyloxy-tridecan-7-one

Base Information

• Chemical Name: (2S,3R,5S,8R,9S,10R,12S)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-8,9-dihydroxy-3-(4-methoxy-benzyloxy)-2,3,10-trimethyl-12-triisopropylsilanyloxy-tridecan-7-one
• CAS No.: 224580-00-1
• Molecular Formula: C₄₅H₈₈O₈Si₃
• Molecular Weight: 841.445
• Mol file: 224580-00-1.mol

Synonyms:(2S,3R,5S,8R,9S,10R,12S)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-8,9-dihydroxy-3-(4-methoxy-benzyloxy)-2,3,10-trimethyl-12-triisopropylsilanyloxy-tridecan-7-one

Chemical Property of (2S,3R,5S,8R,9S,10R,12S)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-8,9-dihydroxy-3-(4-methoxy-benzyloxy)-2,3,10-trimethyl-12-triisopropylsilanyloxy-tridecan-7-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,5S,8R,9S,10R,12S)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-8,9-dihydroxy-3-(4-methoxy-benzyloxy)-2,3,10-trimethyl-12-triisopropylsilanyloxy-tridecan-7-one

There total 18 articles about (2S,3R,5S,8R,9S,10R,12S)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-8,9-dihydroxy-3-(4-methoxy-benzyloxy)-2,3,10-trimethyl-12-triisopropylsilanyloxy-tridecan-7-one 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: 58.0%

(E)-(2S,4R,9S,11R,12S)-9,13-Bis-(tert-butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-4,11,12-trimethyl-2-triisopropylsilanyloxy-tridec-5-en-7-one (224579-99-1) → (2S,3R,5S,8R,9S,10R,12S)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-8,9-dihydroxy-3-(4-methoxy-benzyloxy)-2,3,10-trimethyl-12-triisopropylsilanyloxy-tridecan-7-one (224580-00-1) + (2S,3R,5S,8S,9R,10R,12S)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-8,9-dihydroxy-3-(4-methoxy-benzyloxy)-2,3,10-trimethyl-12-triisopropylsilanyloxy-tridecan-7-one

Guidance literature:

With potassium osmate(VI); AD-mix-α; sodium hydrogencarbonate; hydroquinidein 1,4-phthalazinediyl diether; at 5 ℃; for 36h; Yields of byproduct given;

DOI:10.1016/S0040-4039(99)00207-5

Reference yield:

p-Anisaldehyde dimethyl acetal (2186-92-7) → (2S,3R,5S,8R,9S,10R,12S)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-8,9-dihydroxy-3-(4-methoxy-benzyloxy)-2,3,10-trimethyl-12-triisopropylsilanyloxy-tridecan-7-one (224580-00-1)

Guidance literature:

Multi-step reaction with 16 steps

1: 93 percent / CSA / CH₂Cl₂

2: 86 percent / DIBAL / CH₂Cl₂

3: 97 percent / 2,6-lutidine

4: 1.) O₃, pyr., 2.) Me₂S / 12 h

5: NaBH₄ / ethanol

6: Bu₃P

7: H₂O₂ / tetrahydrofuran

8: K₂OsO₄*H₂O, DHQ₂-PYR / 24 h

9: 86 percent / NaH, tosylimidazole / tetrahydrofuran

10: 91 percent / LiClO₄ / acetonitrile / 12 h / 70 °C

11: 95 percent / 2,6-lutidine

12: 84 percent / DIBAL / hexane

13: n-BuLi

14: NMO, TPAP

15: 95 percent / LiCl, i-Pr₂NEt / acetonitrile / 36 h / Ambient temperature

16: 58 percent / AD-mix α, DHQ2PHAL, K2OsO4*H2O, NaHCO3 / 36 h / 5 °C

With pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; potassium osmate(VI); AD-mix-α; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; (8a,9R,8′′′a,9′′′R)-9,9′-[(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)]bis(6′-methoxy-10,11-dihydrocinchonan); dimethylsulfide; tributylphosphine; camphor-10-sulfonic acid; dihydrogen peroxide; lithium perchlorate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; ozone; hydroquinidein 1,4-phthalazinediyl diether; N-ethyl-N,N-diisopropylamine; N-tosylimidazole; lithium chloride; In tetrahydrofuran; ethanol; hexane; dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(99)00207-5

Reference yield:

(2R,4S)-2-Methyl-4-triisopropylsilanyloxy-pentanal (224579-98-0) → (2S,3R,5S,8R,9S,10R,12S)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-8,9-dihydroxy-3-(4-methoxy-benzyloxy)-2,3,10-trimethyl-12-triisopropylsilanyloxy-tridecan-7-one (224580-00-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / LiCl, i-Pr₂NEt / acetonitrile / 36 h / Ambient temperature

2: 58 percent / AD-mix α, DHQ2PHAL, K2OsO4*H2O, NaHCO3 / 36 h / 5 °C

With potassium osmate(VI); AD-mix-α; sodium hydrogencarbonate; hydroquinidein 1,4-phthalazinediyl diether; N-ethyl-N,N-diisopropylamine; lithium chloride; In acetonitrile;

DOI:10.1016/S0040-4039(99)00207-5

upstream raw materials:

(E)-(2S,4R,9S,11R,12S)-9,13-Bis-(tert-butyl-dimethyl-silanyloxy)-11-(4-methoxy-benzyloxy)-4,11,12-trimethyl-2-triisopropylsilanyloxy-tridec-5-en-7-one

p-Anisaldehyde dimethyl acetal

(2R,4S)-2-Methyl-4-triisopropylsilanyloxy-pentanal

(2R,4S)-2-Methyl-4-triisopropylsilanyloxy-pentan-1-ol

Downstream raw materials:

(2S,3R,5S,8R,9S,10R,12S)-1,5,8,9-Tetrakis-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2,3,10-trimethyl-12-triisopropylsilanyloxy-tridecan-7-one

(2S,3R,5S,8R,9S,10R,12S)-5,8,9-Tris-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-3-(4-methoxy-benzyloxy)-2,3,10-trimethyl-12-triisopropylsilanyloxy-tridecan-7-one