(2S,3S,4S,5R)-methyl 6-(4-formyl-2-methoxyphenoxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylate

Base Information

• Chemical Name: (2S,3S,4S,5R)-methyl 6-(4-formyl-2-methoxyphenoxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylate
• CAS No.: 1301740-26-0
• Molecular Formula: C₁₄H₁₆O₉
• Molecular Weight: 328.276
• Mol file: 1301740-26-0.mol

Synonyms:(2S,3S,4S,5R)-methyl 6-(4-formyl-2-methoxyphenoxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylate

Chemical Property of (2S,3S,4S,5R)-methyl 6-(4-formyl-2-methoxyphenoxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of (2S,3S,4S,5R)-methyl 6-(4-formyl-2-methoxyphenoxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylate

There total 2 articles about (2S,3S,4S,5R)-methyl 6-(4-formyl-2-methoxyphenoxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylate 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: 64.0%

(3R,4S,5S,6S)-2-(4-formyl-2-methoxyphenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (1301740-25-9) → (2S,3S,4S,5R)-methyl 6-(4-formyl-2-methoxyphenoxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylate (1301740-26-0,96107-45-8)

Guidance literature:

With methanol; water; sodium hydroxide; In N,N-dimethyl-formamide; at 20 ℃; for 5h;

DOI:10.1021/jf200272m

Reference yield:

O-(methyl 2,3,4-tri-O-acetyl-D-glucuronopyranosyl)-N-phenyl-2,2,2-trifluoroacetimidate (869996-05-4) → (2S,3S,4S,5R)-methyl 6-(4-formyl-2-methoxyphenoxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylate (1301740-26-0,96107-45-8)

Guidance literature:

Multi-step reaction with 2 steps

1: boron trifluoride diethyl etherate / dichloromethane / 12 h / 20 °C

2: methanol; water; sodium hydroxide / N,N-dimethyl-formamide / 5 h / 20 °C

With methanol; boron trifluoride diethyl etherate; water; sodium hydroxide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jf200272m

Reference yield: 9.0%

C10H14O9 + (2S,3S,4S,5R)-methyl 6-(4-formyl-2-methoxyphenoxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylate (1301740-26-0,96107-45-8) → 5-feruloylquinic acid 4'-O-glucuronide (1301740-23-7)

Guidance literature:

With piperidine; dmap; In N,N-dimethyl-formamide; at 20 ℃; for 168h;

DOI:10.1021/jf200272m

upstream raw materials:

O-(methyl 2,3,4-tri-O-acetyl-D-glucuronopyranosyl)-N-phenyl-2,2,2-trifluoroacetimidate

(3R,4S,5S,6S)-2-(4-formyl-2-methoxyphenoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Downstream raw materials:

5-feruloylquinic acid 4'-O-glucuronide