dimethyl ((methyl 4-O-benzyl-2,3-di-O-methyl-α-D-glucopyranuronyl)methyl)phosphonate

Base Information

• Chemical Name: dimethyl ((methyl 4-O-benzyl-2,3-di-O-methyl-α-D-glucopyranuronyl)methyl)phosphonate
• CAS No.: 150591-91-6
• Molecular Formula: C₁₉H₂₉O₉P
• Molecular Weight: 432.408

Synonyms:dimethyl ((methyl 4-O-benzyl-2,3-di-O-methyl-α-D-glucopyranuronyl)methyl)phosphonate

Chemical Property of dimethyl ((methyl 4-O-benzyl-2,3-di-O-methyl-α-D-glucopyranuronyl)methyl)phosphonate

Chemical Property:

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Technology Process of dimethyl ((methyl 4-O-benzyl-2,3-di-O-methyl-α-D-glucopyranuronyl)methyl)phosphonate

There total 2 articles about dimethyl ((methyl 4-O-benzyl-2,3-di-O-methyl-α-D-glucopyranuronyl)methyl)phosphonate 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: 100.0%

methyl (methyl 4-O-benzyl-2,3-di-O-methyl-α-D-glucopyranosid)uronate (51433-20-6) + dimethyl lithiomethylphosphonate (34939-91-8,58648-56-9) → dimethyl ((methyl 4-O-benzyl-2,3-di-O-methyl-α-D-glucopyranuronyl)methyl)phosphonate (150591-91-6)

Guidance literature:

In tetrahydrofuran; at -78 - 20 ℃;

Reference yield:

methyl (methyl 4-O-benzyl-2,3-di-O-methyl-α-D-glucopyranosid)uronate (51433-20-6) + dimethyl methane phosphonate (756-79-6) → dimethyl ((methyl 4-O-benzyl-2,3-di-O-methyl-α-D-glucopyranuronyl)methyl)phosphonate (150591-91-6)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; Yield given; 1.) -78 deg C, 15 min., 2.) -78 deg C --> room temp., 2 h;

DOI:10.1021/jo00100a047

Reference yield: 90.0%

benzaldehyde (100-52-7) + dimethyl ((methyl 4-O-benzyl-2,3-di-O-methyl-α-D-glucopyranuronyl)methyl)phosphonate (150591-91-6) → (E)-3-Phenyl-1-((4S,5R,6S)-4,5,6-trimethoxy-5,6-dihydro-4H-pyran-2-yl)-propenone

Guidance literature:

With caesium carbonate; In isopropyl alcohol; for 8h; Ambient temperature;

DOI:10.1021/jo00100a047

upstream raw materials:

methyl (methyl 4-O-benzyl-2,3-di-O-methyl-α-D-glucopyranosid)uronate

dimethyl lithiomethylphosphonate

dimethyl methane phosphonate

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