[(2S,3R,5S,7S,8R)-7-(4-Bromo-benzyloxy)-8-(4-bromo-benzyloxymethyl)-3-(4-methoxy-benzyloxy)-5-methyl-oxocan-2-yl]-acetaldehyde

Base Information

Chemical Name:[(2S,3R,5S,7S,8R)-7-(4-Bromo-benzyloxy)-8-(4-bromo-benzyloxymethyl)-3-(4-methoxy-benzyloxy)-5-methyl-oxocan-2-yl]-acetaldehyde
CAS No.:876288-67-4
Molecular Formula:C₃₃H₃₈Br₂O₆
Molecular Weight:690.469
Hs Code.:

Synonyms:[(2S,3R,5S,7S,8R)-7-(4-Bromo-benzyloxy)-8-(4-bromo-benzyloxymethyl)-3-(4-methoxy-benzyloxy)-5-methyl-oxocan-2-yl]-acetaldehyde

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Chemical Property of [(2S,3R,5S,7S,8R)-7-(4-Bromo-benzyloxy)-8-(4-bromo-benzyloxymethyl)-3-(4-methoxy-benzyloxy)-5-methyl-oxocan-2-yl]-acetaldehyde

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Technology Process of [(2S,3R,5S,7S,8R)-7-(4-Bromo-benzyloxy)-8-(4-bromo-benzyloxymethyl)-3-(4-methoxy-benzyloxy)-5-methyl-oxocan-2-yl]-acetaldehyde

There total 9 articles about [(2S,3R,5S,7S,8R)-7-(4-Bromo-benzyloxy)-8-(4-bromo-benzyloxymethyl)-3-(4-methoxy-benzyloxy)-5-methyl-oxocan-2-yl]-acetaldehyde 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: 95.0%

: 876288-74-3
(2R,3S,5S,7R,8S)-3-(4-Bromo-benzyloxy)-2-(4-bromo-benzyloxymethyl)-7-(4-methoxy-benzyloxy)-8-((E)-2-methoxy-vinyl)-5-methyl-oxocane

: 876288-67-4
[(2S,3R,5S,7S,8R)-7-(4-Bromo-benzyloxy)-8-(4-bromo-benzyloxymethyl)-3-(4-methoxy-benzyloxy)-5-methyl-oxocan-2-yl]-acetaldehyde

Guidance literature:: (2R,3S,5S,7R,8S)-3-(4-Bromo-benzyloxy)-2-(4-bromo-benzyloxymethyl)-7-(4-methoxy-benzyloxy)-8-((E)-2-methoxy-vinyl)-5-methyl-oxocane; mercury(II) diacetate; In tetrahydrofuran; water; at 23 ℃; for 1h;

With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; water; for 1.5h;
DOI:10.1016/j.tetlet.2005.11.085

Reference yield:

: 876288-70-9
(2'R,3'S,5'R,7'S,8'R)-2'-(tret-butyldimethylsilyloxymethyl)-7'-hydroxy-8'-hydroxymethyl-5'-methyl-oxocan-3'-yl 2,2-dimethylpropionate

: 876288-67-4
[(2S,3R,5S,7S,8R)-7-(4-Bromo-benzyloxy)-8-(4-bromo-benzyloxymethyl)-3-(4-methoxy-benzyloxy)-5-methyl-oxocan-2-yl]-acetaldehyde

Guidance literature:: Multi-step reaction with 6 steps

1.1: 100 percent / NaH; Bu₄NI / tetrahydrofuran / 14 h / 25 °C

2.1: 88 percent / DIBALH / CH₂Cl₂ / 1.5 h / -78 °C

3.1: NaH; Bu₄NI / tetrahydrofuran / 21 h / 26 °C

4.1: Bu₄NF / tetrahydrofuran / 1.5 h / 0 °C

5.1: Dess-Martin periodinane / CH₂Cl₂ / 0.83 h / 0 - 23 °C

5.2: NHMDS / CH₂Cl₂ / 0.5 h / 0 °C

5.3: 79 percent / aldehyde / CH₂Cl₂ / 17 h / -78 - 25 °C

6.1: Hg(OAc)2 / tetrahydrofuran; H₂O / 1 h / 23 °C

6.2: 95 percent / Bu₄NI / tetrahydrofuran; H₂O / 1.5 h

With tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; mercury(II) diacetate; In tetrahydrofuran; dichloromethane; water; 5.2: Wittig reaction;
DOI:10.1016/j.tetlet.2005.11.085

Reference yield:

: 876288-69-6
(1'R,3'S,4'R,6'R,8'S,10'R)-3'-(tret-butyldimethylsilyloxymethyl)-6'-methyl-10'-phenyl-2',9',11'-trioxabicyclo[6.4.0]dodecan-4'-yl 2,2-dimethylpropionate

: 876288-67-4
[(2S,3R,5S,7S,8R)-7-(4-Bromo-benzyloxy)-8-(4-bromo-benzyloxymethyl)-3-(4-methoxy-benzyloxy)-5-methyl-oxocan-2-yl]-acetaldehyde

Guidance literature:: Multi-step reaction with 7 steps

1.1: 88 percent / HS(CH₂)2SH; NaHCO₃ / Zn(OTf)2 / CH₂Cl₂ / 2 h / 0 - 25 °C

2.1: 100 percent / NaH; Bu₄NI / tetrahydrofuran / 14 h / 25 °C

3.1: 88 percent / DIBALH / CH₂Cl₂ / 1.5 h / -78 °C

4.1: NaH; Bu₄NI / tetrahydrofuran / 21 h / 26 °C

5.1: Bu₄NF / tetrahydrofuran / 1.5 h / 0 °C

6.1: Dess-Martin periodinane / CH₂Cl₂ / 0.83 h / 0 - 23 °C

6.2: NHMDS / CH₂Cl₂ / 0.5 h / 0 °C

6.3: 79 percent / aldehyde / CH₂Cl₂ / 17 h / -78 - 25 °C

7.1: Hg(OAc)2 / tetrahydrofuran; H₂O / 1 h / 23 °C

7.2: 95 percent / Bu₄NI / tetrahydrofuran; H₂O / 1.5 h

With tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; ethane-1,2-dithiol; mercury(II) diacetate; zinc trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; water; 6.2: Wittig reaction;
DOI:10.1016/j.tetlet.2005.11.085