(2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-(3,4-dimethoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-(3,4-dimethoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS No.: 50621-74-4
• Molecular Formula: C₂₂H₂₈O₁₂
• Molecular Weight: 484.457

Synonyms:(2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-(3,4-dimethoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property of (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-(3,4-dimethoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property:

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Technology Process of (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-(3,4-dimethoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 2 articles about (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-(3,4-dimethoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 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: 60.0%

(3,4-dimethoxyphenyl)methanol (93-03-8) + 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester (21085-72-3) → (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-(3,4-dimethoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (50621-74-4)

Guidance literature:

With silver carbonate; In benzene; for 72h; Ambient temperature;

DOI:10.1016/S0040-4039(01)80651-1

Reference yield:

→ (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-(3,4-dimethoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (50621-74-4)

Guidance literature:

entspr. 1-Bromo-Derivat, 3,4-Dimethoxybenzylalkohol/Ag2CO3;

Reference yield: 74.0%

(2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-(3,4-dimethoxy-benzyloxy)-tetrahydro-pyran-2-carboxylic acid methyl ester (50621-74-4) → (2S,3S,4S,5R,6R)-6-(3,4-Dimethoxy-benzyloxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester (126380-61-8) + (2R,3R,4S,5S,6S)-2-(3,4-Dimethoxy-benzyloxy)-6-trimethoxymethyl-tetrahydro-pyran-3,4,5-triol

Guidance literature:

With sodium methylate; In methanol; for 3h; Ambient temperature;

DOI:10.1016/S0040-4039(01)80651-1

upstream raw materials:

(3,4-dimethoxyphenyl)methanol

1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester

Downstream raw materials:

(2S,3S,4S,5R,6R)-6-(3,4-Dimethoxy-benzyloxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

(2S,3S,4S,5R,6S)-6-(5-Benzoyl-6-hydroxy-indane-1-carbonyloxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid

(2S,3S,4S,5R)-3,4,5-Tris-allyloxycarbonyloxy-6-hydroxy-tetrahydro-pyran-2-carboxylic acid benzyl ester

(2S,3S,4S,5R,6S)-6-(5-Benzoyl-6-hydroxy-indane-1-carbonyloxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid benzyl ester

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