(2R,3S,4R,5R,6R)-2-Hydroxymethyl-6-(2,4,6-trimethoxy-phenyl)-tetrahydro-pyran-3,4,5-triol

Base Information

• Chemical Name: (2R,3S,4R,5R,6R)-2-Hydroxymethyl-6-(2,4,6-trimethoxy-phenyl)-tetrahydro-pyran-3,4,5-triol
• CAS No.: 73244-62-9
• Molecular Formula: C₁₅H₂₂O₈
• Molecular Weight: 330.335

Synonyms:(2R,3S,4R,5R,6R)-2-Hydroxymethyl-6-(2,4,6-trimethoxy-phenyl)-tetrahydro-pyran-3,4,5-triol

Chemical Property of (2R,3S,4R,5R,6R)-2-Hydroxymethyl-6-(2,4,6-trimethoxy-phenyl)-tetrahydro-pyran-3,4,5-triol

Chemical Property:

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Technology Process of (2R,3S,4R,5R,6R)-2-Hydroxymethyl-6-(2,4,6-trimethoxy-phenyl)-tetrahydro-pyran-3,4,5-triol

There total 4 articles about (2R,3S,4R,5R,6R)-2-Hydroxymethyl-6-(2,4,6-trimethoxy-phenyl)-tetrahydro-pyran-3,4,5-triol 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: 70.0%

1-deoxy-1-(C-2',4',6'-trimethoxyphenyl)-2,3,4,6-tetra-O-benzyl-D-glucopyranose (93414-74-5) → (2R,3S,4R,5R,6R)-2-Hydroxymethyl-6-(2,4,6-trimethoxy-phenyl)-tetrahydro-pyran-3,4,5-triol (73244-62-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; at 25 ℃; for 12h;

DOI:10.1021/ja00300a036

Reference yield:

1,2,3-trimethoxybenzene (621-23-8) → (2R,3S,4R,5R,6R)-2-Hydroxymethyl-6-(2,4,6-trimethoxy-phenyl)-tetrahydro-pyran-3,4,5-triol (73244-62-9)

Guidance literature:

Multi-step reaction with 2 steps

1: silver(I)triflate / diethyl ether / 3 h / 0 °C

2: H₂ / Pd/C

With hydrogen; silver trifluoromethanesulfonate; palladium on activated charcoal; In diethyl ether;

DOI:10.1016/S0040-4039(00)88003-X

Reference yield:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) → (2R,3S,4R,5R,6R)-2-Hydroxymethyl-6-(2,4,6-trimethoxy-phenyl)-tetrahydro-pyran-3,4,5-triol (73244-62-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 69 percent / tri-n-butyl phosphine / CH₂Cl₂ / 3 h / 25 °C

2: silver(I)triflate / diethyl ether / 3 h / 0 °C

3: H₂ / Pd/C

With tributylphosphine; hydrogen; silver trifluoromethanesulfonate; palladium on activated charcoal; In diethyl ether; dichloromethane;

DOI:10.1016/S0040-4039(00)88003-X

upstream raw materials:

1-deoxy-1-(C-2',4',6'-trimethoxyphenyl)-2,3,4,6-tetra-O-benzyl-D-glucopyranose

1,2,3-trimethoxybenzene

2,3,4,6-Tetra-O-benzyl-D-glucopyranose

2-Pyridyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside

Downstream raw materials:

α-1-deoxy-1-(2',4',6'-trimethoxyphenyl)-2,3,4,6-tetra-O-acetyl-D-glucopyranose

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