2,2-Dimethyl-4-((2R,4aR,6S,8aS)-7-methyl-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-butyraldehyde

Base Information

• Chemical Name: 2,2-Dimethyl-4-((2R,4aR,6S,8aS)-7-methyl-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-butyraldehyde
• CAS No.: 138723-33-8
• Molecular Formula: C₂₀H₂₆O₄
• Molecular Weight: 330.424

Synonyms:

Chemical Property of 2,2-Dimethyl-4-((2R,4aR,6S,8aS)-7-methyl-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-butyraldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-4-((2R,4aR,6S,8aS)-7-methyl-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-butyraldehyde

There total 11 articles about 2,2-Dimethyl-4-((2R,4aR,6S,8aS)-7-methyl-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-butyraldehyde 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:

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (13096-62-3) → 2,2-Dimethyl-4-((2R,4aR,6S,8aS)-7-methyl-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-butyraldehyde (138723-33-8)

Guidance literature:

Multi-step reaction with 10 steps

2: Et₃SiH, BF₃*Et₂O / CH₂Cl₂

3: H₂, HClO₄ / Pd/C / methanol

4: pyridine

5: pyridine / DMAP / CH₂Cl₂

6: 1) nBu₂SnO, 2) Br₂ / 1) PhCH₃, 2) CCl₄

7: 82 percent / tetrahydrofuran

8: NaH, nBu₄NI, CH₃I

9: 63 percent / trimethyl phosphite

10: PCC

With pyridine; triethylsilane; perchloric acid; boron trifluoride diethyl etherate; hydrogen; bromine; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; pyridinium chlorochromate; phosphorous acid trimethyl ester; methyl iodide; dmap; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo00030a005

Reference yield:

(2S,3R,4R,5S,6R)-2-(4-Hydroxy-3,3-dimethyl-butyl)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (138723-42-9) → 2,2-Dimethyl-4-((2R,4aR,6S,8aS)-7-methyl-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-butyraldehyde (138723-33-8)

Guidance literature:

Multi-step reaction with 7 steps

1: pyridine

2: pyridine / DMAP / CH₂Cl₂

3: 1) nBu₂SnO, 2) Br₂ / 1) PhCH₃, 2) CCl₄

4: 82 percent / tetrahydrofuran

5: NaH, nBu₄NI, CH₃I

6: 63 percent / trimethyl phosphite

7: PCC

With pyridine; bromine; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; pyridinium chlorochromate; phosphorous acid trimethyl ester; methyl iodide; dmap; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00030a005

Reference yield:

C19H21LiOSi (138723-27-0) → 2,2-Dimethyl-4-((2R,4aR,6S,8aS)-7-methyl-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-butyraldehyde (138723-33-8)

Guidance literature:

Multi-step reaction with 10 steps

2: Et₃SiH, BF₃*Et₂O / CH₂Cl₂

3: H₂, HClO₄ / Pd/C / methanol

4: pyridine

5: pyridine / DMAP / CH₂Cl₂

6: 1) nBu₂SnO, 2) Br₂ / 1) PhCH₃, 2) CCl₄

7: 82 percent / tetrahydrofuran

8: NaH, nBu₄NI, CH₃I

9: 63 percent / trimethyl phosphite

10: PCC

With pyridine; triethylsilane; perchloric acid; boron trifluoride diethyl etherate; hydrogen; bromine; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; pyridinium chlorochromate; phosphorous acid trimethyl ester; methyl iodide; dmap; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo00030a005

upstream raw materials:

tert-Butyl-[2,2-dimethyl-4-((2R,4aR,6S,8aS)-7-methyl-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-butoxy]-dimethyl-silane

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

(2S,3R,4R,5S,6R)-2-(4-Hydroxy-3,3-dimethyl-butyl)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

C₁₉H₂₁LiOSi

Downstream raw materials:

(2R,4aR,6S,8aS)-6-((Z)-3,3-Dimethyl-hepta-4,6-dienyl)-7-methyl-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxine

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