(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

Base Information

Chemical Name:(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
CAS No.:876288-74-3
Molecular Formula:C₃₄H₄₀Br₂O₆
Molecular Weight:704.496
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 8 articles about (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 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: 79.0%

: 876288-73-2
[(2S,3R,5S,7S,8R)-7-(4-Bromo-benzyloxy)-8-(4-bromo-benzyloxymethyl)-3-(4-methoxy-benzyloxy)-5-methyl-oxocan-2-yl]-methanol

: 4009-98-7
(methoxymethyl)triphenylphosphonium chloride

: 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

Guidance literature:: [(2S,3R,5S,7S,8R)-7-(4-Bromo-benzyloxy)-8-(4-bromo-benzyloxymethyl)-3-(4-methoxy-benzyloxy)-5-methyl-oxocan-2-yl]-methanol; With Dess-Martin periodane; In dichloromethane; at 0 - 23 ℃; for 0.833333h;

(methoxymethyl)triphenylphosphonium chloride; With sodium hexamethyldisilazane; In dichloromethane; at 0 ℃; for 0.5h;

With aldehyde; In dichloromethane; at -78 - 25 ℃; for 17h;
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

: 876288-74-3
(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

Guidance literature:: Multi-step reaction with 6 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

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

Reference yield:

: 475641-60-2
(2R,4aR,6S,7R,9S,10aS)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-9-methyl-2-phenyl-octahydro-1,3,5-trioxa-benzocycloocten-7-ol

: 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

Guidance literature:: Multi-step reaction with 7 steps

1.1: 100 percent / pyridine / 14 h / 26 °C

2.1: 88 percent / HS(CH₂)2SH; NaHCO₃ / Zn(OTf)2 / CH₂Cl₂ / 2 h / 0 - 25 °C

3.1: 100 percent / NaH; Bu₄NI / tetrahydrofuran / 14 h / 25 °C

4.1: 88 percent / DIBALH / CH₂Cl₂ / 1.5 h / -78 °C

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

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

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

7.2: NHMDS / CH₂Cl₂ / 0.5 h / 0 °C

7.3: 79 percent / aldehyde / CH₂Cl₂ / 17 h / -78 - 25 °C

With pyridine; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; ethane-1,2-dithiol; zinc trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; 7.2: Wittig reaction;
DOI:10.1016/j.tetlet.2005.11.085