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

Base Information

• Chemical Name: (1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-2,3-dimethyl-bicyclo[2.2.1]heptane-2-carbaldehyde
• CAS No.: 434342-94-6
• Molecular Formula: C₂₇H₃₄O₅
• Molecular Weight: 438.564
• Mol file: 434342-94-6.mol

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

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

There total 15 articles about (1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-2,3-dimethyl-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: 85.0%

(1R,2R,3R,4S,5S)-5-Benzyloxy-2-benzyloxymethyl-1-methoxymethoxy-2,3-dimethyl-3-((E)-propenyl)-bicyclo[2.2.1]heptane (434342-93-5) → (1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-2,3-dimethyl-bicyclo[2.2.1]heptane-2-carbaldehyde (434342-94-6)

Guidance literature:

(1R,2R,3R,4S,5S)-5-Benzyloxy-2-benzyloxymethyl-1-methoxymethoxy-2,3-dimethyl-3-((E)-propenyl)-bicyclo[2.2.1]heptane; With pyridine; ozone; In methanol; dichloromethane; at -78 ℃;

With dimethylsulfide; In methanol; dichloromethane;

DOI:10.1055/s-2002-19778

Reference yield:

benzyl bromide (100-39-0) → (1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-2,3-dimethyl-bicyclo[2.2.1]heptane-2-carbaldehyde (434342-94-6)

Guidance literature:

Multi-step reaction with 7 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

6.1: O₃; pyridine / methanol; CH₂Cl₂ / -78 °C

6.2: 85 percent / Me₂S / methanol; CH₂Cl₂

With pyridine; sodium periodate; potassium tert-butylate; potassium hydride; ozone; acetic acid; N-ethyl-N,N-diisopropylamine; hydrazine; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; 1,2-dichloro-benzene; butan-1-ol; 5.1: Claisen rearrangement;

DOI:10.1055/s-2002-19778

Reference yield:

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 (213816-61-6) → (1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-2,3-dimethyl-bicyclo[2.2.1]heptane-2-carbaldehyde (434342-94-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: DIBALH / tetrahydrofuran / -78 °C

2.1: 91 percent / aq. AcOH / 60 °C

3.1: 85 percent / aq. NaIO₄ / methanol / 20 °C

4.1: 47 percent / KH / 1,2-dimethoxy-ethane; tetrahydrofuran / -10 °C

5.1: 96 percent / i-Pr₂NEt / 1,2-dichloro-benzene / 160 °C

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

6.2: 67 percent / potassium 3-aminopropylamide / tetrahydrofuran

7.1: O₃; pyridine / methanol; CH₂Cl₂ / -78 °C

7.2: 85 percent / Me₂S / methanol; CH₂Cl₂

With pyridine; sodium periodate; potassium tert-butylate; potassium hydride; diisobutylaluminium hydride; ozone; acetic acid; N-ethyl-N,N-diisopropylamine; hydrazine; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; 1,2-dichloro-benzene; butan-1-ol; 6.1: Claisen rearrangement;

DOI:10.1055/s-2002-19778

upstream raw materials:

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

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

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

Downstream raw materials:

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

((1S,2R,3R,4R,6S)-6-Benzyloxy-3-benzyloxymethyl-4-methoxymethoxy-2,3-dimethyl-bicyclo[2.2.1]hept-2-yl)-methanol