(1R,2R,3R,4S,5S)-5-Benzyloxy-2-benzyloxymethyl-1-methoxymethoxy-2,3-dimethyl-3-((E)-propenyl)-bicyclo[2.2.1]heptane

Base Information

Chemical Name:(1R,2R,3R,4S,5S)-5-Benzyloxy-2-benzyloxymethyl-1-methoxymethoxy-2,3-dimethyl-3-((E)-propenyl)-bicyclo[2.2.1]heptane
CAS No.:434342-93-5
Molecular Formula:C₂₉H₃₈O₄
Molecular Weight:450.618
Hs Code.:

Synonyms:(1R,2R,3R,4S,5S)-5-Benzyloxy-2-benzyloxymethyl-1-methoxymethoxy-2,3-dimethyl-3-((E)-propenyl)-bicyclo[2.2.1]heptane

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1R,2R,3R,4S,5S)-5-Benzyloxy-2-benzyloxymethyl-1-methoxymethoxy-2,3-dimethyl-3-((E)-propenyl)-bicyclo[2.2.1]heptane

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Technology Process of (1R,2R,3R,4S,5S)-5-Benzyloxy-2-benzyloxymethyl-1-methoxymethoxy-2,3-dimethyl-3-((E)-propenyl)-bicyclo[2.2.1]heptane

There total 15 articles about (1R,2R,3R,4S,5S)-5-Benzyloxy-2-benzyloxymethyl-1-methoxymethoxy-2,3-dimethyl-3-((E)-propenyl)-bicyclo[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: 67.0%

: 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

: 434342-93-5
(1R,2R,3R,4S,5S)-5-Benzyloxy-2-benzyloxymethyl-1-methoxymethoxy-2,3-dimethyl-3-((E)-propenyl)-bicyclo[2.2.1]heptane

Guidance literature:: (1S,2S,3R,4R,6S)-2-Allyl-6-benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-3-methyl-bicyclo[2.2.1]heptane-2-carbaldehyde; With potassium tert-butylate; hydrazine; In butan-1-ol; at 180 ℃;

With potassium salt of 1,3-diaminopropane; In tetrahydrofuran;
DOI:10.1055/s-2002-19778

Reference yield:

: 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

: 434342-93-5
(1R,2R,3R,4S,5S)-5-Benzyloxy-2-benzyloxymethyl-1-methoxymethoxy-2,3-dimethyl-3-((E)-propenyl)-bicyclo[2.2.1]heptane

: (1R,2R,3R,4S,5S)-3-Allyl-5-benzyloxy-2-benzyloxymethyl-1-methoxymethoxy-2,3-dimethyl-bicyclo[2.2.1]heptane

Guidance literature:: With potassium tert-butylate; hydrazine; In butan-1-ol; at 180 ℃; Title compound not separated from byproducts;
DOI:10.1055/s-2002-19778

Reference yield:

: 100-39-0
benzyl bromide

: 434342-93-5
(1R,2R,3R,4S,5S)-5-Benzyloxy-2-benzyloxymethyl-1-methoxymethoxy-2,3-dimethyl-3-((E)-propenyl)-bicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 6 steps

1.1: 91 percent / aq. AcOH / 60 °C

2.1: 85 percent / aq. NaIO₄ / methanol / 20 °C

3.1: 47 percent / KH / 1,2-dimethoxy-ethane; tetrahydrofuran / -10 °C

4.1: 96 percent / i-Pr₂NEt / 1,2-dichloro-benzene / 160 °C

5.1: NH₂NH₂; t-BuOK / butan-1-ol / 180 °C

5.2: 67 percent / potassium 3-aminopropylamide / tetrahydrofuran

With sodium periodate; potassium tert-butylate; potassium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; hydrazine; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; 1,2-dichloro-benzene; butan-1-ol; 5.1: Claisen rearrangement;
DOI:10.1055/s-2002-19778