dimethyl <3α,4α-bis(benzyloxy)-5β-hydroxytetrahydro-2H-pyran-2β-yl>malonate

Base Information

• Chemical Name: dimethyl <3α,4α-bis(benzyloxy)-5β-hydroxytetrahydro-2H-pyran-2β-yl>malonate
• CAS No.: 115479-61-3
• Molecular Formula: C₂₄H₂₈O₈
• Molecular Weight: 444.482
• Mol file: 115479-61-3.mol

Synonyms:dimethyl <3α,4α-bis(benzyloxy)-5β-hydroxytetrahydro-2H-pyran-2β-yl>malonate

Chemical Property of dimethyl <3α,4α-bis(benzyloxy)-5β-hydroxytetrahydro-2H-pyran-2β-yl>malonate

Chemical Property:

Purity/Quality:

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Technology Process of dimethyl <3α,4α-bis(benzyloxy)-5β-hydroxytetrahydro-2H-pyran-2β-yl>malonate

There total 4 articles about dimethyl <3α,4α-bis(benzyloxy)-5β-hydroxytetrahydro-2H-pyran-2β-yl>malonate 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: 90.0%

dimethyl 3-exo-acetoxy-5,6-endo-bis(benzyloxy)-7-oxabicyclo<2.2.1>heptane-2,2-dicarboxylate (115479-57-7) → dimethyl <3α,4α-bis(benzyloxy)-5β-hydroxytetrahydro-2H-pyran-2β-yl>malonate (115479-61-3)

Guidance literature:

With sodium tetrahydroborate; potassium carbonate; In methanol; 1.) 0 deg C, 30 min, 2.) RT, 4 h;

DOI:10.1021/jo00258a013

Reference yield: 4.0%

dimethyl 3-exo-acetoxy-5,6-endo-bis(benzyloxy)-7-oxabicyclo<2.2.1>heptane-2,2-dicarboxylate (115479-57-7) → dimethyl <3α,4α-bis(benzyloxy)-5β-hydroxytetrahydro-2H-pyran-2β-yl>malonate (115479-61-3) + 2-((2S,3S,4R,5S)-3,4-Bis-benzyloxy-5-hydroxy-tetrahydro-pyran-2-yl)-3-hydroxy-propionic acid methyl ester (115479-62-4,115511-69-8)

Guidance literature:

With sodium tetrahydroborate; potassium carbonate; In methanol;

DOI:10.1246/cl.1987.2257

Reference yield:

3,4-bis(benzoloxy)furan (53996-40-0) → dimethyl <3α,4α-bis(benzyloxy)-5β-hydroxytetrahydro-2H-pyran-2β-yl>malonate (115479-61-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 57 percent / neat (no solvent) / 40 °C

2: 10percentPd-C / methanol

3: 90 percent / K₂CO₃/NaBH₄ / methanol

With sodium tetrahydroborate; potassium carbonate; 10% palladium on active carbon; In methanol;

DOI:10.1246/cl.1987.2257

upstream raw materials:

dimethyl 3-exo-acetoxy-5,6-endo-bis(benzyloxy)-7-oxabicyclo<2.2.1>heptane-2,2-dicarboxylate

3,4-bis(benzoloxy)furan

dimethyl 6-exo-acetoxy-2,3-bis(benzyloxy)-7-oxabicyclo<2.2.1>hept-2-ene-5,5-dicarboxylate

Downstream raw materials:

dimethyl <5β-acetoxy-3α,4α-bis(benzyloxy)tetrahydro-2H-pyran-2β-yl>malonate