(3aR,5R,6S,7S,7aR)-5-Hydroxymethyl-2-(4-methoxy-phenyl)-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol

Base Information

• Chemical Name: (3aR,5R,6S,7S,7aR)-5-Hydroxymethyl-2-(4-methoxy-phenyl)-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol
• CAS No.: 790672-73-0
• Molecular Formula: C₁₄H₁₈O₇
• Molecular Weight: 298.293

Synonyms:(3aR,5R,6S,7S,7aR)-5-Hydroxymethyl-2-(4-methoxy-phenyl)-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol

Chemical Property of (3aR,5R,6S,7S,7aR)-5-Hydroxymethyl-2-(4-methoxy-phenyl)-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol

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Technology Process of (3aR,5R,6S,7S,7aR)-5-Hydroxymethyl-2-(4-methoxy-phenyl)-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol

There total 2 articles about (3aR,5R,6S,7S,7aR)-5-Hydroxymethyl-2-(4-methoxy-phenyl)-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol 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%

3,4,6-tri-O-p-methoxybenzoyl-1,2-O-p-methoxybenzylidene-α-D-glucopyranose (790672-71-8) → (3aR,5R,6S,7S,7aR)-5-Hydroxymethyl-2-(4-methoxy-phenyl)-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol (790672-73-0)

Guidance literature:

With sodium methylate; In methanol;

DOI:10.1081/CAR-200030087

Reference yield:

C38H35BrO13 → (3aR,5R,6S,7S,7aR)-5-Hydroxymethyl-2-(4-methoxy-phenyl)-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol (790672-73-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / sodium borohydride; potassium iodide / acetonitrile

2: 100 percent / sodium methoxide / methanol

With sodium tetrahydroborate; sodium methylate; potassium iodide; In methanol; acetonitrile;

DOI:10.1081/CAR-200030087

Reference yield: 69.0%

benzyl bromide (100-39-0) + (3aR,5R,6S,7S,7aR)-5-Hydroxymethyl-2-(4-methoxy-phenyl)-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol (790672-73-0) → 3,4,6-tri-O-benzyl-1,2-O-(S)-p-methoxybenzylidene-α-D-glucopyranose (790672-77-4) + 3,4,6-tri-O-benzyl-1,2-O-(R)-p-methoxybenzylidene-α-D-glucopyranose (790672-74-1)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1081/CAR-200030087

upstream raw materials:

3,4,6-tri-O-p-methoxybenzoyl-1,2-O-p-methoxybenzylidene-α-D-glucopyranose

Downstream raw materials:

3,4,6-tri-O-benzyl-1,2-O-(S)-p-methoxybenzylidene-α-D-glucopyranose

3,4,6-tri-O-benzyl-1,2-O-(R)-p-methoxybenzylidene-α-D-glucopyranose

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