(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

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Chemical Name:(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
CAS No.:905732-40-3
Molecular Formula:C₃₂H₆₂O₇Si₂
Molecular Weight:615.011
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 11 articles about (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 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: 54.0%

: 905732-39-0
(2S,3S,4R,5R,6S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-[(4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxolan-4-yl]-2,4-dimethyl-heptane-1,4-diol

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

: 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

Guidance literature:: With chloro-trimethyl-silane; 4 A molecular sieve; sodium cyanoborohydride; In acetonitrile; at 0 ℃; for 0.166667h;
DOI:10.1016/j.tetlet.2006.05.010

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 9 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

With 2,6-dimethylpyridine; osmium(VIII) oxide; chloro-trimethyl-silane; 4 A molecular sieve; camphor-10-sulfonic acid; diisobutylaluminium hydride; sodium cyanoborohydride; N-ethyl-N,N-diisopropylamine; titanium tetrachloride; In methanol; dichloromethane; water; acetone; acetonitrile;
DOI:10.1016/j.tetlet.2006.05.010

Reference yield:

: 143680-12-0
(E)-5-Benzyloxy-2,4-dimethyl-2-penten-1-ol

: 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

Guidance literature:: Multi-step reaction with 10 steps

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

2.1: 85 percent / i-Pr₂NEt / TiCl₄ / CH₂Cl₂ / 3 h / -78 °C

3.1: 2,6-lutidine / CH₂Cl₂ / 1 h / 0 - 20 °C

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

5.1: 2,6-lutidine / CH₂Cl₂ / 0.08 h / 0 °C

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

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

7.2: CSA / CH₂Cl₂ / 1 h / 0 - 20 °C

7.3: 80 percent / TBAF / tetrahydrofuran / 6 h / 0 - 20 °C

8.1: 84 percent / OsO₄ / acetone; H₂O / 12 h / 0 - 20 °C

9.1: 2,6-lutidine / CH₂Cl₂ / 2 h / 0 - 20 °C

9.2: 74 percent / H₂ / Pd/C / ethyl acetate / 5 h

10.1: 54 percent / NaCNBH₃; TMSCl; 4 Angstroem molecular sieves / acetonitrile / 0.17 h / 0 °C

With 2,6-dimethylpyridine; osmium(VIII) oxide; 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; dichloromethane; water; dimethyl sulfoxide; acetone; acetonitrile;
DOI:10.1016/j.tetlet.2006.05.010