[(4R,4aS,8αR)-2,2-dimethyl-6-oxo-4,4α,6,8α-tetrahydropyron(3,2δ)(1,3)-dioxin-4-yl]methyl benzoate

Base Information

• Chemical Name: [(4R,4aS,8αR)-2,2-dimethyl-6-oxo-4,4α,6,8α-tetrahydropyron(3,2δ)(1,3)-dioxin-4-yl]methyl benzoate
• CAS No.: 1239353-06-0
• Molecular Formula: C₁₇H₁₈O₆
• Molecular Weight: 318.326
• Mol file: 1239353-06-0.mol

Synonyms:[(4R,4aS,8αR)-2,2-dimethyl-6-oxo-4,4α,6,8α-tetrahydropyron(3,2δ)(1,3)-dioxin-4-yl]methyl benzoate

Chemical Property of [(4R,4aS,8αR)-2,2-dimethyl-6-oxo-4,4α,6,8α-tetrahydropyron(3,2δ)(1,3)-dioxin-4-yl]methyl benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(4R,4aS,8αR)-2,2-dimethyl-6-oxo-4,4α,6,8α-tetrahydropyron(3,2δ)(1,3)-dioxin-4-yl]methyl benzoate

There total 4 articles about [(4R,4aS,8αR)-2,2-dimethyl-6-oxo-4,4α,6,8α-tetrahydropyron(3,2δ)(1,3)-dioxin-4-yl]methyl benzoate 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%

{(4R,5S,6R)-5-(benzyloxy)-6-[(Z)-3-methoxy-3-oxoprop-1-enyl]-2,2-dimethyl-1,3-dioxan-4-yl}methyl benzoate (1456695-47-8) → [(4R,4aS,8αR)-2,2-dimethyl-6-oxo-4,4α,6,8α-tetrahydropyron(3,2δ)(1,3)-dioxin-4-yl]methyl benzoate (1239353-06-0)

Guidance literature:

With ammonia; sodium; In tetrahydrofuran; at -30 ℃; for 0.5h;

DOI:10.1016/j.tetlet.2013.07.164

Reference yield:

[(4R,5S,6R)-5-(benzyloxy)-6-(hydroxylmethyl)-2,2-dimethyl-1,3-dioxan-4-yl]methyl benzoate (1456695-46-7) → [(4R,4aS,8αR)-2,2-dimethyl-6-oxo-4,4α,6,8α-tetrahydropyron(3,2δ)(1,3)-dioxin-4-yl]methyl benzoate (1239353-06-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 2 h / -78 °C

2: sodium hydride / tetrahydrofuran / 1 h / -78 °C

3: sodium; ammonia / tetrahydrofuran / 0.5 h / -30 °C

With ammonia; sodium; sodium hydride; In tetrahydrofuran; 1: |Swern Oxidation / 2: |Still-Gennary Z-Olefination;

DOI:10.1016/j.tetlet.2013.07.164

Reference yield:

C22H24O6 → [(4R,4aS,8αR)-2,2-dimethyl-6-oxo-4,4α,6,8α-tetrahydropyron(3,2δ)(1,3)-dioxin-4-yl]methyl benzoate (1239353-06-0)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydride / tetrahydrofuran / 1 h / -78 °C

2: sodium; ammonia / tetrahydrofuran / 0.5 h / -30 °C

With ammonia; sodium; sodium hydride; In tetrahydrofuran; 1: |Still-Gennary Z-Olefination;

DOI:10.1016/j.tetlet.2013.07.164

upstream raw materials:

benzoic acid anhydride

[(4R,5S,6R)-5-(benzyloxy)-6-(hydroxylmethyl)-2,2-dimethyl-1,3-dioxan-4-yl]methyl benzoate

{(4R,5S,6R)-5-(benzyloxy)-6-[(Z)-3-methoxy-3-oxoprop-1-enyl]-2,2-dimethyl-1,3-dioxan-4-yl}methyl benzoate

Downstream raw materials:

C₁₄H₁₄O₆

2,3-dideoxy-D-arabino-hept-2-enoic acid δ-lactone 4,6-diacetate 7-benzoate