(1R,2R,3S,4S,7R,8S)-7,8-Bis-benzyloxymethyl-1-methyl-bicyclo[2.2.2]oct-5-ene-2,3-diol

Base Information

Chemical Name:(1R,2R,3S,4S,7R,8S)-7,8-Bis-benzyloxymethyl-1-methyl-bicyclo[2.2.2]oct-5-ene-2,3-diol
CAS No.:176659-51-1
Molecular Formula:C₂₅H₃₀O₄
Molecular Weight:394.511
Hs Code.:

Synonyms:(1R,2R,3S,4S,7R,8S)-7,8-Bis-benzyloxymethyl-1-methyl-bicyclo[2.2.2]oct-5-ene-2,3-diol

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Chemical Property of (1R,2R,3S,4S,7R,8S)-7,8-Bis-benzyloxymethyl-1-methyl-bicyclo[2.2.2]oct-5-ene-2,3-diol

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Technology Process of (1R,2R,3S,4S,7R,8S)-7,8-Bis-benzyloxymethyl-1-methyl-bicyclo[2.2.2]oct-5-ene-2,3-diol

There total 4 articles about (1R,2R,3S,4S,7R,8S)-7,8-Bis-benzyloxymethyl-1-methyl-bicyclo[2.2.2]oct-5-ene-2,3-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: 100.0%

: 176659-50-0
(1R,2R,6S,7S,10R,11S)-10,11-Bis-benzyloxymethyl-1,4,4-trimethyl-3,5-dioxa-tricyclo[5.2.2.0^2,6]undec-8-ene

: 176659-51-1
(1R,2R,3S,4S,7R,8S)-7,8-Bis-benzyloxymethyl-1-methyl-bicyclo[2.2.2]oct-5-ene-2,3-diol

Guidance literature:: With acetic acid; at 80 ℃; for 16h;
DOI:10.1039/cc9960000869

Reference yield:

: 114763-30-3
(3aR,7aS)-2,2,4-trimethyl-3a,7a-dihydro-1,3-benzodioxole

: 176659-51-1
(1R,2R,3S,4S,7R,8S)-7,8-Bis-benzyloxymethyl-1-methyl-bicyclo[2.2.2]oct-5-ene-2,3-diol

Guidance literature:: Multi-step reaction with 4 steps

1: 68 percent / CH₂Cl₂ / 24 h / 0 - 18 °C

2: 88 percent / LiAlH₄ / tetrahydrofuran / 3 h / 66 °C

3: 99 percent / NaH, Bu₄NI / dimethylformamide / 18 h / 0 - 18 °C

4: 100 percent / aq. AcOH / 16 h / 80 °C

With lithium aluminium tetrahydride; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1039/cc9960000869

Reference yield:

: 176659-49-7
((1S,2S,6R,7R,8R,9S)-9-Hydroxymethyl-4,4,7-trimethyl-3,5-dioxa-tricyclo[5.2.2.0^2,6]undec-10-en-8-yl)-methanol

: 176659-51-1
(1R,2R,3S,4S,7R,8S)-7,8-Bis-benzyloxymethyl-1-methyl-bicyclo[2.2.2]oct-5-ene-2,3-diol

Guidance literature:: Multi-step reaction with 2 steps

1: 99 percent / NaH, Bu₄NI / dimethylformamide / 18 h / 0 - 18 °C

2: 100 percent / aq. AcOH / 16 h / 80 °C

With tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; In N,N-dimethyl-formamide;
DOI:10.1039/cc9960000869