(2R,3S,5S,6S,9R,10S)-9-(3,4-Dimethoxy-benzyloxymethoxy)-5-methoxy-10-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-2,6-dimethyl-undecane-1,3-diol

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Chemical Name:(2R,3S,5S,6S,9R,10S)-9-(3,4-Dimethoxy-benzyloxymethoxy)-5-methoxy-10-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-2,6-dimethyl-undecane-1,3-diol
CAS No.:740836-27-5
Molecular Formula:C₃₀H₅₂O₉
Molecular Weight:556.737
Hs Code.:

Synonyms:(2R,3S,5S,6S,9R,10S)-9-(3,4-Dimethoxy-benzyloxymethoxy)-5-methoxy-10-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-2,6-dimethyl-undecane-1,3-diol

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Chemical Property of (2R,3S,5S,6S,9R,10S)-9-(3,4-Dimethoxy-benzyloxymethoxy)-5-methoxy-10-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-2,6-dimethyl-undecane-1,3-diol

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Technology Process of (2R,3S,5S,6S,9R,10S)-9-(3,4-Dimethoxy-benzyloxymethoxy)-5-methoxy-10-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-2,6-dimethyl-undecane-1,3-diol

There total 23 articles about (2R,3S,5S,6S,9R,10S)-9-(3,4-Dimethoxy-benzyloxymethoxy)-5-methoxy-10-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-2,6-dimethyl-undecane-1,3-diol 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: 99.0%

: 740836-26-4
(2R,3R)-2-[(1S,2R,5S,6S,8S,9R)-8,10-Bis-(tert-butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-benzyloxymethoxy)-6-methoxy-1,5,9-trimethyl-decyl]-5-methoxy-3-methyl-tetrahydro-furan

: 740836-27-5
(2R,3S,5S,6S,9R,10S)-9-(3,4-Dimethoxy-benzyloxymethoxy)-5-methoxy-10-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-2,6-dimethyl-undecane-1,3-diol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h;
DOI:10.1016/j.tet.2006.06.046

Reference yield:

: 73814-98-9,73814-99-0,105560-79-0,143005-16-7
(2R,3S)-5-Benzyloxy-2-methyl-pentane-1,3-diol

: 740836-27-5
(2R,3S,5S,6S,9R,10S)-9-(3,4-Dimethoxy-benzyloxymethoxy)-5-methoxy-10-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-2,6-dimethyl-undecane-1,3-diol

Guidance literature:: Multi-step reaction with 14 steps

1.1: 8.15 g / imidazole / dimethylformamide / 11 h / 50 °C

2.1: 92 percent / H₂; NaHCO₃ / Pd/C / ethyl acetate / 11 h / 20 °C

3.1: 89 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 0 °C

4.1: dibutylboron triflate; Et₃N / CH₂Cl₂ / 0.67 h / 0 °C

4.2: 100 percent / CH₂Cl₂ / 2.33 h / -78 - 0 °C

5.1: 100 percent / LiBH₄; EtOH / 0.5 h / -10 °C

6.1: 99 percent / tributylphosphine / dimethylformamide / 11 h / 20 °C

7.1: 99 percent / m-chloroperoxybenzoic acid; NaHCO₃ / CH₂Cl₂ / 0.33 h / 0 - 20 °C

8.1: 95 percent / NaH / tetrahydrofuran / 16 h / 20 °C

9.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

9.2: 67 percent / tetrahydrofuran; hexane / -78 °C

10.1: 196 mg / sodium amalgam; Na₂HPO₄ / methanol / 2 h / 0 °C

11.1: 89 percent / Ca; iPrOH; liquid NH₃ / tetrahydrofuran / 1.5 h / -78 °C

12.1: 95 percent / H₂; NaHCO₃ / Pd/C / ethanol / 18 h / 20 °C

13.1: 84 percent / iPr₂NEt / CH₂Cl₂ / 3 h / 20 °C

14.1: 99 percent / Bu₄NF / tetrahydrofuran / 2 h / 20 °C

With 1H-imidazole; disodium hydrogenphosphate; sodium amalgam; lithium borohydride; n-butyllithium; oxalyl dichloride; ethanol; tributylphosphine; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; ammonia; hydrogen; sodium hydride; sodium hydrogencarbonate; calcium; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; isopropyl alcohol; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 9.2: Julia coupling;
DOI:10.1016/j.tet.2006.06.046

Reference yield:

: 179944-88-8
(2S,3R)-2-Benzyloxy-3-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-butyraldehyde

: 740836-27-5
(2R,3S,5S,6S,9R,10S)-9-(3,4-Dimethoxy-benzyloxymethoxy)-5-methoxy-10-((2R,3R)-5-methoxy-3-methyl-tetrahydro-furan-2-yl)-2,6-dimethyl-undecane-1,3-diol

Guidance literature:: Multi-step reaction with 6 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 67 percent / tetrahydrofuran; hexane / -78 °C

2.1: 196 mg / sodium amalgam; Na₂HPO₄ / methanol / 2 h / 0 °C

3.1: 89 percent / Ca; iPrOH; liquid NH₃ / tetrahydrofuran / 1.5 h / -78 °C

4.1: 95 percent / H₂; NaHCO₃ / Pd/C / ethanol / 18 h / 20 °C

5.1: 84 percent / iPr₂NEt / CH₂Cl₂ / 3 h / 20 °C

6.1: 99 percent / Bu₄NF / tetrahydrofuran / 2 h / 20 °C

With disodium hydrogenphosphate; sodium amalgam; n-butyllithium; tetrabutyl ammonium fluoride; ammonia; hydrogen; sodium hydrogencarbonate; calcium; N-ethyl-N,N-diisopropylamine; isopropyl alcohol; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; 1.2: Julia coupling;
DOI:10.1016/j.tet.2006.06.046