(2S,3S,4S,7S,9S,10S)-7,9-bis(tert-butyldimethylsilanyloxy)-3-(4-methoxybenzyloxy)-2,4,10-trimethyl-13-trityloxytrideca-5,11-dien-1-ol

Base Information

Chemical Name:(2S,3S,4S,7S,9S,10S)-7,9-bis(tert-butyldimethylsilanyloxy)-3-(4-methoxybenzyloxy)-2,4,10-trimethyl-13-trityloxytrideca-5,11-dien-1-ol
CAS No.:672296-38-7
Molecular Formula:C₅₅H₈₀O₆Si₂
Molecular Weight:893.408
Hs Code.:

Synonyms:(2S,3S,4S,7S,9S,10S)-7,9-bis(tert-butyldimethylsilanyloxy)-3-(4-methoxybenzyloxy)-2,4,10-trimethyl-13-trityloxytrideca-5,11-dien-1-ol

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Chemical Property of (2S,3S,4S,7S,9S,10S)-7,9-bis(tert-butyldimethylsilanyloxy)-3-(4-methoxybenzyloxy)-2,4,10-trimethyl-13-trityloxytrideca-5,11-dien-1-ol

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Technology Process of (2S,3S,4S,7S,9S,10S)-7,9-bis(tert-butyldimethylsilanyloxy)-3-(4-methoxybenzyloxy)-2,4,10-trimethyl-13-trityloxytrideca-5,11-dien-1-ol

There total 12 articles about (2S,3S,4S,7S,9S,10S)-7,9-bis(tert-butyldimethylsilanyloxy)-3-(4-methoxybenzyloxy)-2,4,10-trimethyl-13-trityloxytrideca-5,11-dien-1-ol 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: 74.0%

: 672296-37-6
4-[4 (S), 6 (S)-BIS-(TERT-BUTYL-DIMETHYL-SILANYLOXY)-1 ⁽⁵⁾, 7 (R)-dimethyl-10-trityloxy-deca-2,8-DIENYL]-2-(4-METHOXY-BENZYL)-5 S-METHYL-[1,3 (R)]dioxane

: 672296-38-7
(2S,3S,4S,7S,9S,10S)-7,9-bis(tert-butyldimethylsilanyloxy)-3-(4-methoxybenzyloxy)-2,4,10-trimethyl-13-trityloxytrideca-5,11-dien-1-ol

Guidance literature:: With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 - 0 ℃; for 1h;

Reference yield: 74.0%

: 951154-73-7
4(S)-[4(S),6(S)-bis(tert-butyldimethylsilanyloxy)-1(S),7(S)-dimethyl-10-trityloxydeca-2,8-dienyl]-2(R)-(4-methoxyphenyl)-5(S)-methyl[1,3]dioxane

: 672296-38-7
(2S,3S,4S,7S,9S,10S)-7,9-bis(tert-butyldimethylsilanyloxy)-3-(4-methoxybenzyloxy)-2,4,10-trimethyl-13-trityloxytrideca-5,11-dien-1-ol

Guidance literature:: With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 - 0 ℃;
DOI:10.1016/j.tet.2007.05.033

Reference yield:

: C₁₁H₂₀O₅

: 672296-38-7
(2S,3S,4S,7S,9S,10S)-7,9-bis(tert-butyldimethylsilanyloxy)-3-(4-methoxybenzyloxy)-2,4,10-trimethyl-13-trityloxytrideca-5,11-dien-1-ol

Guidance literature:: Multi-step reaction with 8 steps

1.1: 2.96 g / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

2.1: 65 percent / HF*pyridine complex; pyridine / tetrahydrofuran / 20 °C

3.1: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h

4.1: NaHMDS / tetrahydrofuran / -78 - 20 °C

4.2: 75 percent / tetrahydrofuran / -78 - 20 °C

5.1: aq. KOH / ethanol; tetrahydrofuran / 6 h / Heating

6.1: Et₃N / tetrahydrofuran / 0.25 h / -10 °C

6.2: 1.79 g / NaBH₄ / tetrahydrofuran; H₂O / 0 °C

7.1: 99 percent / 4-(dimethylamino)pyridine; pyridine / 18 h / Heating

8.1: 74 percent / diisobutylaluminum hydride / hexane; CH₂Cl₂ / -78 - 0 °C

With pyridine; 2,6-dimethylpyridine; dmap; potassium hydroxide; sodium hexamethyldisilazane; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; In tetrahydrofuran; ethanol; hexane; dichloromethane; 3.1: Dess-Martin oxidation / 4.2: Wittig coupling;
DOI:10.1016/j.tet.2007.05.033