Acetic acid (2S,3S,4R,5R,6S,7S,8S)-8-acetoxy-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-7-(4-methoxy-benzyloxy)-2,4,6-trimethyl-nonyl ester

Base Information

Chemical Name:Acetic acid (2S,3S,4R,5R,6S,7S,8S)-8-acetoxy-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-7-(4-methoxy-benzyloxy)-2,4,6-trimethyl-nonyl ester
CAS No.:905732-42-5
Molecular Formula:C₃₆H₆₆O₉Si₂
Molecular Weight:699.086
Hs Code.:

Synonyms:Acetic acid (2S,3S,4R,5R,6S,7S,8S)-8-acetoxy-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-7-(4-methoxy-benzyloxy)-2,4,6-trimethyl-nonyl ester

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Chemical Property of Acetic acid (2S,3S,4R,5R,6S,7S,8S)-8-acetoxy-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-7-(4-methoxy-benzyloxy)-2,4,6-trimethyl-nonyl ester

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Technology Process of Acetic acid (2S,3S,4R,5R,6S,7S,8S)-8-acetoxy-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-7-(4-methoxy-benzyloxy)-2,4,6-trimethyl-nonyl ester

There total 12 articles about Acetic acid (2S,3S,4R,5R,6S,7S,8S)-8-acetoxy-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-7-(4-methoxy-benzyloxy)-2,4,6-trimethyl-nonyl ester 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%

: 905732-40-3
(2S,3S,4R,5R,6S,7S,8S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-2,4,6-trimethyl-nonane-1,4,8-triol

: 108-24-7
acetic anhydride

: 905732-42-5
Acetic acid (2S,3S,4R,5R,6S,7S,8S)-8-acetoxy-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-7-(4-methoxy-benzyloxy)-2,4,6-trimethyl-nonyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1016/j.tetlet.2006.05.010

Reference yield:

: 373645-82-0
(E)-(R)-5-Benzyloxy-2,4-dimethyl-pent-2-enal

: 905732-42-5
Acetic acid (2S,3S,4R,5R,6S,7S,8S)-8-acetoxy-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-7-(4-methoxy-benzyloxy)-2,4,6-trimethyl-nonyl ester

Guidance literature:: Multi-step reaction with 10 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

With 2,6-dimethylpyridine; dmap; osmium(VIII) oxide; chloro-trimethyl-silane; 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:

: 143680-11-9
(E)-5-Benzyloxy-2,3-dimethyl-2-pentensaeureethylester

: 905732-42-5
Acetic acid (2S,3S,4R,5R,6S,7S,8S)-8-acetoxy-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-7-(4-methoxy-benzyloxy)-2,4,6-trimethyl-nonyl ester

Guidance literature:: Multi-step reaction with 12 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

With 2,6-dimethylpyridine; dmap; osmium(VIII) oxide; lithium aluminium tetrahydride; chloro-trimethyl-silane; 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