(1S,2R,5S,6S)-2-(2,3-Dimethoxy-phenyl)-6-methoxymethoxy-bicyclo[3.2.1]oct-3-en-2-ol

Base Information

Chemical Name:(1S,2R,5S,6S)-2-(2,3-Dimethoxy-phenyl)-6-methoxymethoxy-bicyclo[3.2.1]oct-3-en-2-ol
CAS No.:358753-66-9
Molecular Formula:C₁₈H₂₄O₅
Molecular Weight:320.386
Hs Code.:

Synonyms:(1S,2R,5S,6S)-2-(2,3-Dimethoxy-phenyl)-6-methoxymethoxy-bicyclo[3.2.1]oct-3-en-2-ol

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Chemical Property of (1S,2R,5S,6S)-2-(2,3-Dimethoxy-phenyl)-6-methoxymethoxy-bicyclo[3.2.1]oct-3-en-2-ol

Chemical Property:

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Technology Process of (1S,2R,5S,6S)-2-(2,3-Dimethoxy-phenyl)-6-methoxymethoxy-bicyclo[3.2.1]oct-3-en-2-ol

There total 1 articles about (1S,2R,5S,6S)-2-(2,3-Dimethoxy-phenyl)-6-methoxymethoxy-bicyclo[3.2.1]oct-3-en-2-ol 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:

: 91-16-7
1,2-dimethoxybenzene

: 351033-77-7
(1S,5S,6S)-6-Methoxymethoxy-bicyclo[3.2.1]oct-3-en-2-one

: 358753-66-9
(1S,2R,5S,6S)-2-(2,3-Dimethoxy-phenyl)-6-methoxymethoxy-bicyclo[3.2.1]oct-3-en-2-ol

Guidance literature:: 1,2-dimethoxybenzene; With n-butyllithium; at -78 ℃;

(1S,5S,6S)-6-Methoxymethoxy-bicyclo[3.2.1]oct-3-en-2-one; In tetrahydrofuran; at -78 ℃;
DOI:10.1039/b101668g

Reference yield:

: 358753-66-9
(1S,2R,5S,6S)-2-(2,3-Dimethoxy-phenyl)-6-methoxymethoxy-bicyclo[3.2.1]oct-3-en-2-ol

: 358753-67-0
(1R,5S,7S)-4-(2,3-Dimethoxy-phenyl)-7-methoxymethoxy-bicyclo[3.2.1]oct-3-en-2-one

Guidance literature:: With pyridinium chlorochromate; In dichloromethane;
DOI:10.1039/b101668g

Reference yield:

: 358753-66-9
(1S,2R,5S,6S)-2-(2,3-Dimethoxy-phenyl)-6-methoxymethoxy-bicyclo[3.2.1]oct-3-en-2-ol

: 207731-95-1
1,2,3,3a(R),9a(R),9b(S)-hexahydro-5-methoxy-9b-[2-[N-methyl-N-(phenylsulfonyl)amino]ethyl]-3-(ethylenedioxy)phenanthro[4,4a,4b,5-bcd]furan

Guidance literature:: Multi-step reaction with 10 steps

1.1: PCC / CH₂Cl₂

2.1: 75 percent / CuBr*Me₂S / hexamethylphosphoric acid triamide; tetrahydrofuran

3.1: NBS / CH₂Cl₂ / 20 °C

4.1: 82 percent / dimethylformamide / 0.5 h / Heating

5.1: 71 percent / TfOTMS / CH₂Cl₂

6.1: BH₃-Me₂S

6.2: 72 percent / aq. H₂O₂; NaOH

7.1: 87 percent / pyridine

8.1: 50 percent / (CH₂OH)2; p-TsOH / benzene / 15 h / Heating

9.1: 100 percent / LiAlH₄ / tetrahydrofuran / 20 °C

10.1: 1,1'-(azodicarbonyl)dipiperidine; Bu₃P / tetrahydrofuran

With pyridine; N-Bromosuccinimide; lithium aluminium tetrahydride; copper(I) bromide dimethylsulfide complex; tributylphosphine; trimethylsilyl trifluoromethanesulfonate; dimethylsulfide borane complex; toluene-4-sulfonic acid; ethylene glycol; pyridinium chlorochromate; 1,1'-azodicarbonyl-dipiperidine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide; benzene; 10.1: Mitsunobu reaction;
DOI:10.1039/b101668g