(+)-(1S,4S,5S,6S)-6-exo-(Benzyloxy)-2,2-dimethoxy-1,5-endo-dimethyl-7-oxabicyclo<2.2.1>heptane

Base Information

Chemical Name:(+)-(1S,4S,5S,6S)-6-exo-(Benzyloxy)-2,2-dimethoxy-1,5-endo-dimethyl-7-oxabicyclo<2.2.1>heptane
CAS No.:161317-36-8
Molecular Formula:C₁₇H₂₄O₄
Molecular Weight:292.375
Hs Code.:

Synonyms:(+)-(1S,4S,5S,6S)-6-exo-(Benzyloxy)-2,2-dimethoxy-1,5-endo-dimethyl-7-oxabicyclo<2.2.1>heptane

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Chemical Property of (+)-(1S,4S,5S,6S)-6-exo-(Benzyloxy)-2,2-dimethoxy-1,5-endo-dimethyl-7-oxabicyclo<2.2.1>heptane

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Technology Process of (+)-(1S,4S,5S,6S)-6-exo-(Benzyloxy)-2,2-dimethoxy-1,5-endo-dimethyl-7-oxabicyclo<2.2.1>heptane

There total 5 articles about (+)-(1S,4S,5S,6S)-6-exo-(Benzyloxy)-2,2-dimethoxy-1,5-endo-dimethyl-7-oxabicyclo<2.2.1>heptane 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: 83.0%

: 100-39-0
benzyl bromide

: 161317-35-7
(+)-(1S,4S,5S,6S)-6-exo-Hydroxy-2,2-dimethoxy-1,5-endo-dimethyl-7-oxabicyclo<2.2.1>heptane

: 161317-36-8
(+)-(1S,4S,5S,6S)-6-exo-(Benzyloxy)-2,2-dimethoxy-1,5-endo-dimethyl-7-oxabicyclo<2.2.1>heptane

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran;
DOI:10.1021/jo00099a020

Reference yield:

: 3710-43-8
2,4-dimethylfuran

: 161317-36-8
(+)-(1S,4S,5S,6S)-6-exo-(Benzyloxy)-2,2-dimethoxy-1,5-endo-dimethyl-7-oxabicyclo<2.2.1>heptane

Guidance literature:: Multi-step reaction with 5 steps

1: 61 percent / ZnI₂ / 24 h / 55 °C

2: 1.) aq. KOH, 2.) 36percent aq. formaline / 1.) THF, 20 deg C, 2 h, 2.) 30 min

3: Montmorillonite / hexane / 2 h / 20 °C

4: 1.) BH₃*Me₂S, 2.) NaBO₃*4H₂O / 1.) Et₂O, 20 deg C, 2 h, 2.) H₂O, overnight

5: 83 percent / NaH, Bu₄NI / tetrahydrofuran

With sodium perborate; potassium hydroxide; Montmorillonite; formaldehyd; dimethylsulfide borane complex; tetra-(n-butyl)ammonium iodide; sodium hydride; zinc(II) iodide; In tetrahydrofuran; hexane;
DOI:10.1021/jo00099a020

Reference yield:

: 161441-92-5
(1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1S,2R,4S)-2-cyano-1,5-dimethyl-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl ester

: 161317-36-8
(+)-(1S,4S,5S,6S)-6-exo-(Benzyloxy)-2,2-dimethoxy-1,5-endo-dimethyl-7-oxabicyclo<2.2.1>heptane

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) aq. KOH, 2.) 36percent aq. formaline / 1.) THF, 20 deg C, 2 h, 2.) 30 min

2: Montmorillonite / hexane / 2 h / 20 °C

3: 1.) BH₃*Me₂S, 2.) NaBO₃*4H₂O / 1.) Et₂O, 20 deg C, 2 h, 2.) H₂O, overnight

4: 83 percent / NaH, Bu₄NI / tetrahydrofuran

With sodium perborate; potassium hydroxide; Montmorillonite; formaldehyd; dimethylsulfide borane complex; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; hexane;
DOI:10.1021/jo00099a020