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

Base Information

• Chemical Name: (1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-3-methyl-bicyclo[2.2.1]heptane-2-carbaldehyde
• CAS No.: 434342-77-5
• Molecular Formula: C₂₆H₃₂O₅
• Molecular Weight: 424.537
• Mol file: 434342-77-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about (1S,2R,3R,4R,6S)-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: 99.0%

chloromethyl methyl ether (107-30-2) + (1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-hydroxy-3-methyl-bicyclo[2.2.1]heptane-2-carbaldehyde (434342-91-3) → (1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-3-methyl-bicyclo[2.2.1]heptane-2-carbaldehyde (434342-77-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃;

DOI:10.1055/s-2002-19778

Reference yield: 85.0%

(S)-1-((1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-3-methyl-bicyclo[2.2.1]hept-2-yl)-ethane-1,2-diol → (1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-3-methyl-bicyclo[2.2.1]heptane-2-carbaldehyde (434342-77-5)

Guidance literature:

With sodium periodate; In methanol; at 20 ℃;

DOI:10.1055/s-2002-19778

Reference yield:

benzyl bromide (100-39-0) → (1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-3-methyl-bicyclo[2.2.1]heptane-2-carbaldehyde (434342-77-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / aq. AcOH / 60 °C

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

With sodium periodate; acetic acid; In methanol;

DOI:10.1055/s-2002-19778

upstream raw materials:

chloromethyl methyl ether

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

benzyl bromide

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

Downstream raw materials:

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

(1R,2R,3R,4S,5S)-3-Benzenesulfinylmethyl-5-benzyloxy-2-benzyloxymethyl-1-methoxymethoxy-2-methyl-bicyclo[2.2.1]heptane

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

(1R,2R,3R,4S,5S)-5-Benzyloxy-2-benzyloxymethyl-1-methoxymethoxy-2-methyl-3-phenylsulfanylmethyl-bicyclo[2.2.1]heptane