(1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-hydroxy-3-methyl-bicyclo[2.2.1]heptane-2-carbaldehyde

Base Information

Chemical Name:(1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-hydroxy-3-methyl-bicyclo[2.2.1]heptane-2-carbaldehyde
CAS No.:434342-91-3
Molecular Formula:C₂₄H₂₈O₄
Molecular Weight:380.484
Hs Code.:

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

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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 (1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-hydroxy-3-methyl-bicyclo[2.2.1]heptane-2-carbaldehyde

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

There total 5 articles about (1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-hydroxy-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: 77.0%

: 434342-90-2
(S)-1-((1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-hydroxy-3-methyl-bicyclo[2.2.1]hept-2-yl)-2-methyl-propane-1,2-diol

: 434342-91-3
(1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-hydroxy-3-methyl-bicyclo[2.2.1]heptane-2-carbaldehyde

Guidance literature:: With sodium periodate; In methanol; at 20 ℃;
DOI:10.1055/s-2002-19778

Reference yield:

: 434342-74-2
(E)-2-Methyl-3-((S)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-acrylic acid ethyl ester

: 434342-91-3
(1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-hydroxy-3-methyl-bicyclo[2.2.1]heptane-2-carbaldehyde

Guidance literature:: Multi-step reaction with 5 steps

1: 62 percent / LDA / tetrahydrofuran / -78 °C

2: 99 percent / DIBALH / tetrahydrofuran / -78 °C

3: 84 percent / NaH / tetrahydrofuran; dimethylformamide / 20 °C

4: 92 percent / aq. AcOH / 60 °C

5: 77 percent / aq. NaIO₄ / methanol / 20 °C

With sodium periodate; sodium hydride; diisobutylaluminium hydride; acetic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 1: Michael reaction;
DOI:10.1055/s-2002-19778

Reference yield:

: 434342-89-9
(1S,2S,4R,5R,6R)-5-Hydroxymethyl-4-methoxymethoxy-5-methyl-6-((S)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-bicyclo[2.2.1]heptan-2-ol

: 434342-91-3
(1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-hydroxy-3-methyl-bicyclo[2.2.1]heptane-2-carbaldehyde

Guidance literature:: Multi-step reaction with 3 steps

1: 84 percent / NaH / tetrahydrofuran; dimethylformamide / 20 °C

2: 92 percent / aq. AcOH / 60 °C

3: 77 percent / aq. NaIO₄ / methanol / 20 °C

With sodium periodate; sodium hydride; acetic acid; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1055/s-2002-19778