(2R,3S,4S,5R,6S,7S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2,4,6-trimethyl-8-oxo-4-triethylsilanyloxy-nonanoic acid

Base Information

• Chemical Name: (2R,3S,4S,5R,6S,7S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2,4,6-trimethyl-8-oxo-4-triethylsilanyloxy-nonanoic acid
• CAS No.: 905732-44-7
• Molecular Formula: C₃₈H₇₂O₈Si₃
• Molecular Weight: 741.241

Synonyms:(2R,3S,4S,5R,6S,7S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2,4,6-trimethyl-8-oxo-4-triethylsilanyloxy-nonanoic acid

Chemical Property of (2R,3S,4S,5R,6S,7S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2,4,6-trimethyl-8-oxo-4-triethylsilanyloxy-nonanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of (2R,3S,4S,5R,6S,7S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2,4,6-trimethyl-8-oxo-4-triethylsilanyloxy-nonanoic acid

There total 15 articles about (2R,3S,4S,5R,6S,7S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2,4,6-trimethyl-8-oxo-4-triethylsilanyloxy-nonanoic acid 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: 86.0%

(2S,3S,4R,5R,6S,7S,8S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2,4,6-trimethyl-4-triethylsilanyloxy-nonane-1,8-diol (905732-43-6) → (2R,3S,4S,5R,6S,7S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2,4,6-trimethyl-8-oxo-4-triethylsilanyloxy-nonanoic acid (905732-44-7)

Guidance literature:

(2S,3S,4R,5R,6S,7S,8S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2,4,6-trimethyl-4-triethylsilanyloxy-nonane-1,8-diol; With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; In dichloromethane; for 0.166667h;

With sodium chlorite; sodium dihydrogenphosphate; at 20 ℃; for 0.5h;

DOI:10.1016/j.tetlet.2006.05.010

Reference yield:

(E)-(R)-5-Benzyloxy-2,4-dimethyl-pent-2-enal (373645-82-0) → (2R,3S,4S,5R,6S,7S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2,4,6-trimethyl-8-oxo-4-triethylsilanyloxy-nonanoic acid (905732-44-7)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 85 percent / i-Pr₂NEt / TiCl₄ / CH₂Cl₂ / 3 h / -78 °C

2.1: 2,6-lutidine / CH₂Cl₂ / 1 h / 0 - 20 °C

3.1: CSA / CH₂Cl₂; methanol / 8 h / 0 °C

4.1: 2,6-lutidine / CH₂Cl₂ / 0.08 h / 0 °C

5.1: DIBAL-H / CH₂Cl₂ / 0.25 h / -78 °C

6.1: CSA / CH₂Cl₂; methanol / 0.25 h / 0 °C

6.2: CSA / CH₂Cl₂ / 1 h / 0 - 20 °C

6.3: 80 percent / TBAF / tetrahydrofuran / 6 h / 0 - 20 °C

7.1: 84 percent / OsO₄ / acetone; H₂O / 12 h / 0 - 20 °C

8.1: 2,6-lutidine / CH₂Cl₂ / 2 h / 0 - 20 °C

8.2: 74 percent / H₂ / Pd/C / ethyl acetate / 5 h

9.1: 54 percent / NaCNBH₃; TMSCl; 4 Angstroem molecular sieves / acetonitrile / 0.17 h / 0 °C

10.1: 100 percent / Et₃N; DMAP / CH₂Cl₂ / 0.5 h / 0 °C

11.1: 2,6-lutidine / CH₂Cl₂ / 36 h / 0 - 20 °C

11.2: 75 percent / DIBAL-H / CH₂Cl₂ / 0.17 h / -78 °C

12.1: TPAP; 4 Angstroem molecular sieves; NMO / CH₂Cl₂ / 0.17 h

12.2: 86 percent / NaClO₂; NaH₂PO₄*H₂O / various solvent(s) / 0.5 h / 20 °C

With 2,6-dimethylpyridine; dmap; osmium(VIII) oxide; chloro-trimethyl-silane; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; camphor-10-sulfonic acid; diisobutylaluminium hydride; sodium cyanoborohydride; triethylamine; N-ethyl-N,N-diisopropylamine; titanium tetrachloride; In methanol; dichloromethane; water; acetone; acetonitrile;

DOI:10.1016/j.tetlet.2006.05.010

Reference yield:

(E)-5-Benzyloxy-2,3-dimethyl-2-pentensaeureethylester (143680-11-9) → (2R,3S,4S,5R,6S,7S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2,4,6-trimethyl-8-oxo-4-triethylsilanyloxy-nonanoic acid (905732-44-7)

Guidance literature:

Multi-step reaction with 14 steps

1.1: LAH / diethyl ether / 0.17 h / 0 °C

2.1: SO₃-Py; Et₃N / dimethylsulfoxide; CH₂Cl₂ / 0.5 h / 0 °C

3.1: 85 percent / i-Pr₂NEt / TiCl₄ / CH₂Cl₂ / 3 h / -78 °C

4.1: 2,6-lutidine / CH₂Cl₂ / 1 h / 0 - 20 °C

5.1: CSA / CH₂Cl₂; methanol / 8 h / 0 °C

6.1: 2,6-lutidine / CH₂Cl₂ / 0.08 h / 0 °C

7.1: DIBAL-H / CH₂Cl₂ / 0.25 h / -78 °C

8.1: CSA / CH₂Cl₂; methanol / 0.25 h / 0 °C

8.2: CSA / CH₂Cl₂ / 1 h / 0 - 20 °C

8.3: 80 percent / TBAF / tetrahydrofuran / 6 h / 0 - 20 °C

9.1: 84 percent / OsO₄ / acetone; H₂O / 12 h / 0 - 20 °C

10.1: 2,6-lutidine / CH₂Cl₂ / 2 h / 0 - 20 °C

10.2: 74 percent / H₂ / Pd/C / ethyl acetate / 5 h

11.1: 54 percent / NaCNBH₃; TMSCl; 4 Angstroem molecular sieves / acetonitrile / 0.17 h / 0 °C

12.1: 100 percent / Et₃N; DMAP / CH₂Cl₂ / 0.5 h / 0 °C

13.1: 2,6-lutidine / CH₂Cl₂ / 36 h / 0 - 20 °C

13.2: 75 percent / DIBAL-H / CH₂Cl₂ / 0.17 h / -78 °C

14.1: TPAP; 4 Angstroem molecular sieves; NMO / CH₂Cl₂ / 0.17 h

14.2: 86 percent / NaClO₂; NaH₂PO₄*H₂O / various solvent(s) / 0.5 h / 20 °C

With 2,6-dimethylpyridine; dmap; osmium(VIII) oxide; lithium aluminium tetrahydride; chloro-trimethyl-silane; N-methyl-2-indolinone; tetrapropylammonium perruthennate; pyridine-SO₃ complex; 4 A molecular sieve; camphor-10-sulfonic acid; diisobutylaluminium hydride; sodium cyanoborohydride; triethylamine; N-ethyl-N,N-diisopropylamine; titanium tetrachloride; In methanol; diethyl ether; dichloromethane; water; dimethyl sulfoxide; acetone; acetonitrile;

DOI:10.1016/j.tetlet.2006.05.010

upstream raw materials:

(2S,3S,4R,5R,6S,7S,8S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2,4,6-trimethyl-4-triethylsilanyloxy-nonane-1,8-diol

(E)-(R)-5-Benzyloxy-2,4-dimethyl-pent-2-enal

(E)-(2S,4R,5R,8R)-9-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-4,6,8-trimethyl-non-6-en-3-one

(E)-(2R,3R,6R)-7-Benzyloxy-2-[(4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxolan-4-yl]-4,6-dimethyl-hept-4-en-3-ol

Downstream raw materials:

(2R,3S,4S,5R,6S,7S,8S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-8-hydroxy-7-(4-methoxy-benzyloxy)-2,4,6-trimethyl-4-triethylsilanyloxy-nonanoic acid

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