(1S,4R)-1-<(E)-2-<(3aR,5R,6R,6aR)-6-(benzyloxy)-5-<2-(tert-butyldimethylsilyloxy)ethyl>-tetrahydro-2,2-dimethylfuro<2,3-d>-1,3-dioxol-6-yl>vinyl>-7,7-dimethylbicyclo<2.2.1>-heptan-2-one

Base Information

Chemical Name:(1S,4R)-1-<(E)-2-<(3aR,5R,6R,6aR)-6-(benzyloxy)-5-<2-(tert-butyldimethylsilyloxy)ethyl>-tetrahydro-2,2-dimethylfuro<2,3-d>-1,3-dioxol-6-yl>vinyl>-7,7-dimethylbicyclo<2.2.1>-heptan-2-one
CAS No.:220325-42-8
Molecular Formula:C₃₃H₅₀O₆Si
Molecular Weight:570.842
Hs Code.:

(1S,4R)-1-<(E)-2-<(3aR,5R,6R,6aR)-6-(benzyloxy)-5-<2-(tert-butyldimethylsilyloxy)ethyl>-tetrahydro-2,2-dimethylfuro<2,3-d>-1,3-dioxol-6-yl>vinyl>-7,7-dimethylbicyclo<2.2.1>-heptan-2-one

Synonyms:(1S,4R)-1-<(E)-2-<(3aR,5R,6R,6aR)-6-(benzyloxy)-5-<2-(tert-butyldimethylsilyloxy)ethyl>-tetrahydro-2,2-dimethylfuro<2,3-d>-1,3-dioxol-6-yl>vinyl>-7,7-dimethylbicyclo<2.2.1>-heptan-2-one

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Chemical Property of (1S,4R)-1-<(E)-2-<(3aR,5R,6R,6aR)-6-(benzyloxy)-5-<2-(tert-butyldimethylsilyloxy)ethyl>-tetrahydro-2,2-dimethylfuro<2,3-d>-1,3-dioxol-6-yl>vinyl>-7,7-dimethylbicyclo<2.2.1>-heptan-2-one

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Technology Process of (1S,4R)-1-<(E)-2-<(3aR,5R,6R,6aR)-6-(benzyloxy)-5-<2-(tert-butyldimethylsilyloxy)ethyl>-tetrahydro-2,2-dimethylfuro<2,3-d>-1,3-dioxol-6-yl>vinyl>-7,7-dimethylbicyclo<2.2.1>-heptan-2-one

There total 13 articles about (1S,4R)-1-<(E)-2-<(3aR,5R,6R,6aR)-6-(benzyloxy)-5-<2-(tert-butyldimethylsilyloxy)ethyl>-tetrahydro-2,2-dimethylfuro<2,3-d>-1,3-dioxol-6-yl>vinyl>-7,7-dimethylbicyclo<2.2.1>-heptan-2-one 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: 89.0%

: 100-39-0
benzyl bromide

: 220325-41-7
(1S,4R)-1-<(E)-2-<(3aR,5R,6R,6aR)-5-<2-(tert-butyldimethylsilyloxy)ethyl>-tetrahydro-6-hydroxy-2,2-dimethylfuro<2,3-d>-1,3-dioxol-6-yl>vinyl>-7,7-dimethylbicyclo<2.2.1>-heptan-2-one

: 220325-42-8
(1S,4R)-1-<(E)-2-<(3aR,5R,6R,6aR)-6-(benzyloxy)-5-<2-(tert-butyldimethylsilyloxy)ethyl>-tetrahydro-2,2-dimethylfuro<2,3-d>-1,3-dioxol-6-yl>vinyl>-7,7-dimethylbicyclo<2.2.1>-heptan-2-one

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; for 4h; Ambient temperature;
DOI:10.1021/jo982002w

Reference yield:

: 24807-96-3
3-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose

: 220325-42-8
(1S,4R)-1-<(E)-2-<(3aR,5R,6R,6aR)-6-(benzyloxy)-5-<2-(tert-butyldimethylsilyloxy)ethyl>-tetrahydro-2,2-dimethylfuro<2,3-d>-1,3-dioxol-6-yl>vinyl>-7,7-dimethylbicyclo<2.2.1>-heptan-2-one

Guidance literature:: Multi-step reaction with 9 steps

1: 1) Ph₃P, imidazole, iodine, 2) aq. NaOH / 1) toluene, 80 deg C, 3 h, 2) methanol, RT, 30 min

2: 1) 2-methyl-2-butene, borane-THF, 2) aq. NaOH, H₂O₂ / 1) THF, 0 deg C, 1 h, 2) RT

3: 90 percent / imidazole / CH₂Cl₂ / 1 h / 0 °C

4: 92 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h

5: 50 percent / n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 °C

6: 98 percent / LiAlH₄ / tetrahydrofuran / 3 h / Heating

7: 92 percent / imidazole / CH₂Cl₂ / 1 h / 0 °C

8: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h

9: 89 percent / NaH, tetra-n-butylammonium iodide / dimethylformamide / 4 h / Ambient temperature

With 1H-imidazole; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; borane-THF; 2-methyl-but-2-ene; dihydrogen peroxide; iodine; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo982002w

Reference yield:

: 16713-80-7
3-O-acetyl-1,2:5,6-Di-O-isopropylidene-α-D-glucofuranose

: 220325-42-8
(1S,4R)-1-<(E)-2-<(3aR,5R,6R,6aR)-6-(benzyloxy)-5-<2-(tert-butyldimethylsilyloxy)ethyl>-tetrahydro-2,2-dimethylfuro<2,3-d>-1,3-dioxol-6-yl>vinyl>-7,7-dimethylbicyclo<2.2.1>-heptan-2-one

Guidance literature:: Multi-step reaction with 10 steps

1: 87 percent / aq. acetic acid / 24 h / 20 °C

2: 1) Ph₃P, imidazole, iodine, 2) aq. NaOH / 1) toluene, 80 deg C, 3 h, 2) methanol, RT, 30 min

3: 1) 2-methyl-2-butene, borane-THF, 2) aq. NaOH, H₂O₂ / 1) THF, 0 deg C, 1 h, 2) RT

4: 90 percent / imidazole / CH₂Cl₂ / 1 h / 0 °C

5: 92 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h

6: 50 percent / n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 °C

7: 98 percent / LiAlH₄ / tetrahydrofuran / 3 h / Heating

8: 92 percent / imidazole / CH₂Cl₂ / 1 h / 0 °C

9: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h

10: 89 percent / NaH, tetra-n-butylammonium iodide / dimethylformamide / 4 h / Ambient temperature

With 1H-imidazole; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; borane-THF; 2-methyl-but-2-ene; dihydrogen peroxide; iodine; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; acetic acid; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo982002w