2-((2R,5S,6R)-6-((S)-2-methoxy-4-(4-methoxybenzyloxy)butyl)-5-methyl-5,6-dihydro-2H-pyran-2-yl)acetaldehyde

Base Information

• Chemical Name: 2-((2R,5S,6R)-6-((S)-2-methoxy-4-(4-methoxybenzyloxy)butyl)-5-methyl-5,6-dihydro-2H-pyran-2-yl)acetaldehyde
• CAS No.: 1275506-40-5
• Molecular Formula: C₂₁H₃₀O₅
• Molecular Weight: 362.466

Synonyms:2-((2R,5S,6R)-6-((S)-2-methoxy-4-(4-methoxybenzyloxy)butyl)-5-methyl-5,6-dihydro-2H-pyran-2-yl)acetaldehyde

Chemical Property of 2-((2R,5S,6R)-6-((S)-2-methoxy-4-(4-methoxybenzyloxy)butyl)-5-methyl-5,6-dihydro-2H-pyran-2-yl)acetaldehyde

Chemical Property:

Purity/Quality:

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Technology Process of 2-((2R,5S,6R)-6-((S)-2-methoxy-4-(4-methoxybenzyloxy)butyl)-5-methyl-5,6-dihydro-2H-pyran-2-yl)acetaldehyde

There total 10 articles about 2-((2R,5S,6R)-6-((S)-2-methoxy-4-(4-methoxybenzyloxy)butyl)-5-methyl-5,6-dihydro-2H-pyran-2-yl)acetaldehyde 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: 92.0%

(2R,3S,6R)-6-allyl-2-((S)-2-methoxy-4-(4-methoxybenzyloxy)butyl)-3-methyl-3,6-dihydro-2H-pyran (1219715-13-5) → 2-((2R,5S,6R)-6-((S)-2-methoxy-4-(4-methoxybenzyloxy)butyl)-5-methyl-5,6-dihydro-2H-pyran-2-yl)acetaldehyde (1275506-40-5)

Guidance literature:

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; In 1,4-dioxane; water; toluene; at 20 ℃; for 3h; Darkness;

DOI:10.1021/ol200223q

Reference yield:

(E)-ethyl 3-((2R,3R)-3-((S)-2-methoxy-4-(4-methoxybenzyloxy)butyl)oxiran-2-yl)acrylate (1275506-35-8) → 2-((2R,5S,6R)-6-((S)-2-methoxy-4-(4-methoxybenzyloxy)butyl)-5-methyl-5,6-dihydro-2H-pyran-2-yl)acetaldehyde (1275506-40-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: dichloromethane; toluene / 0.17 h / -40 °C / Inert atmosphere

1.2: 3 h / -40 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / dichloromethane / 0.58 h / -78 °C / Inert atmosphere

3.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

4.1: iodine / tetrahydrofuran / 0.75 h / 0 - 20 °C / Inert atmosphere

5.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water; toluene / 3 h / 20 °C / Darkness

With 2,6-dimethylpyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium periodate; osmium(VIII) oxide; [bis(acetoxy)iodo]benzene; iodine; diisobutylaluminium hydride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; toluene;

DOI:10.1021/ol200223q

Reference yield:

(R)-1-methoxy-4-((3-methoxyhex-5-enyloxy)methyl)benzene (1275506-31-4) → 2-((2R,5S,6R)-6-((S)-2-methoxy-4-(4-methoxybenzyloxy)butyl)-5-methyl-5,6-dihydro-2H-pyran-2-yl)acetaldehyde (1275506-40-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: Hoveyda-Grubbs catalyst / dichloromethane / 3 h / 20 °C / Inert atmosphere

2.1: α,α-diphenyl-2-pyrrolidinemethanol trimethylsilyl ether; dihydrogen peroxide / dichloromethane / 2 h / 20 °C

3.1: dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

4.1: dichloromethane; toluene / 0.17 h / -40 °C / Inert atmosphere

4.2: 3 h / -40 °C / Inert atmosphere

5.1: diisobutylaluminium hydride / dichloromethane / 0.58 h / -78 °C / Inert atmosphere

6.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

7.1: iodine / tetrahydrofuran / 0.75 h / 0 - 20 °C / Inert atmosphere

8.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water; toluene / 3 h / 20 °C / Darkness

With 2,6-dimethylpyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium periodate; osmium(VIII) oxide; [bis(acetoxy)iodo]benzene; α,α-diphenyl-2-pyrrolidinemethanol trimethylsilyl ether; dihydrogen peroxide; iodine; diisobutylaluminium hydride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; toluene;

DOI:10.1021/ol200223q

upstream raw materials:

(2R,3S,6R)-6-allyl-2-((S)-2-methoxy-4-(4-methoxybenzyloxy)butyl)-3-methyl-3,6-dihydro-2H-pyran

(R)-1-methoxy-4-((3-methoxyhex-5-enyloxy)methyl)benzene

(R,E)-5-methoxy-7-(4-methoxybenzyloxy)hept-2-enal

(E)-ethyl 3-((2R,3R)-3-((S)-2-methoxy-4-(4-methoxybenzyloxy)butyl)oxiran-2-yl)acrylate

Downstream raw materials:

2-((2R,5S,6R)-6-((S)-2-methoxy-4-(4-methoxybenzyloxy)butyl)-5-methyl-5,6-dihydro-2H-pyran-2-yl)acetic acid

methyl 2-((2S,5S,6R)-6-((S)-2-methoxy-4-(4-methoxybenzyloxy)butyl)-5-methyltetrahydro-2H-pyran-2-yl)acetate

dimethyl 3-((2S,5S,6R)-6-((S)-2-methoxy-4-(4-methoxybenzyloxy)butyl)-5-methyltetrahydro-2H-pyran-2-yl)-2-oxopropylphosphonate

(E)-1-((2S,5S,6R)-6-((S)-2-methoxy-4-(4-methoxybenzyloxy)butyl)-5-methyltetrahydro-2H-pyran-2-yl)-6-methylhept-3-en-2-one

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