(1S,2S,3R,4R,6S)-2-Allyl-6-benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-3-methyl-bicyclo[2.2.1]heptane-2-carbaldehyde

Base Information

Chemical Name:(1S,2S,3R,4R,6S)-2-Allyl-6-benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-3-methyl-bicyclo[2.2.1]heptane-2-carbaldehyde
CAS No.:434342-83-3
Molecular Formula:C₂₉H₃₆O₅
Molecular Weight:464.602
Hs Code.:

Synonyms:(1S,2S,3R,4R,6S)-2-Allyl-6-benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-3-methyl-bicyclo[2.2.1]heptane-2-carbaldehyde

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Chemical Property of (1S,2S,3R,4R,6S)-2-Allyl-6-benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-3-methyl-bicyclo[2.2.1]heptane-2-carbaldehyde

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Technology Process of (1S,2S,3R,4R,6S)-2-Allyl-6-benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-3-methyl-bicyclo[2.2.1]heptane-2-carbaldehyde

There total 13 articles about (1S,2S,3R,4R,6S)-2-Allyl-6-benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-3-methyl-bicyclo[2.2.1]heptane-2-carbaldehyde 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: 96.0%

: 434342-82-2
(1R,2R,4S,5S)-3-[1-Allyloxy-meth-(E)-ylidene]-5-benzyloxy-2-benzyloxymethyl-1-methoxymethoxy-2-methyl-bicyclo[2.2.1]heptane

: 434342-83-3
(1S,2S,3R,4R,6S)-2-Allyl-6-benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-3-methyl-bicyclo[2.2.1]heptane-2-carbaldehyde

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-benzene; at 160 ℃;
DOI:10.1055/s-2002-19778

Reference yield:

: 100-39-0
benzyl bromide

: 434342-83-3
(1S,2S,3R,4R,6S)-2-Allyl-6-benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-3-methyl-bicyclo[2.2.1]heptane-2-carbaldehyde

Guidance literature:: Multi-step reaction with 5 steps

1: 91 percent / aq. AcOH / 60 °C

2: 85 percent / aq. NaIO₄ / methanol / 20 °C

3: 47 percent / KH / 1,2-dimethoxy-ethane; tetrahydrofuran / -10 °C

4: 96 percent / i-Pr₂NEt / 1,2-dichloro-benzene / 160 °C

With sodium periodate; potassium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; 1,2-dichloro-benzene; 5: Claisen rearrangement;
DOI:10.1055/s-2002-19778

Reference yield:

: 213816-61-6
ethyl (1R,2S,3R,4S)-3-((S)-2,2-dimethyl[1,3]dioxolan-4-yl)-1-methoxymethoxy-2-methyl-5-oxobicyclo[2.2.1]heptane-2-carboxylate

: 434342-83-3
(1S,2S,3R,4R,6S)-2-Allyl-6-benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-3-methyl-bicyclo[2.2.1]heptane-2-carbaldehyde

Guidance literature:: Multi-step reaction with 6 steps

1: DIBALH / tetrahydrofuran / -78 °C

2: 91 percent / aq. AcOH / 60 °C

3: 85 percent / aq. NaIO₄ / methanol / 20 °C

4: 47 percent / KH / 1,2-dimethoxy-ethane; tetrahydrofuran / -10 °C

5: 96 percent / i-Pr₂NEt / 1,2-dichloro-benzene / 160 °C

With sodium periodate; potassium hydride; diisobutylaluminium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; 1,2-dichloro-benzene; 6: Claisen rearrangement;
DOI:10.1055/s-2002-19778