Acetic acid (2R,3R,4R,5R,6S)-4,5-diacetoxy-2-(5-bromomethyl-2-methoxy-phenyl)-6-methyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4R,5R,6S)-4,5-diacetoxy-2-(5-bromomethyl-2-methoxy-phenyl)-6-methyl-tetrahydro-pyran-3-yl ester
• CAS No.: 263148-79-4
• Molecular Formula: C₂₀H₂₅BrO₈
• Molecular Weight: 473.318

Synonyms:Acetic acid (2R,3R,4R,5R,6S)-4,5-diacetoxy-2-(5-bromomethyl-2-methoxy-phenyl)-6-methyl-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2R,3R,4R,5R,6S)-4,5-diacetoxy-2-(5-bromomethyl-2-methoxy-phenyl)-6-methyl-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2R,3R,4R,5R,6S)-4,5-diacetoxy-2-(5-bromomethyl-2-methoxy-phenyl)-6-methyl-tetrahydro-pyran-3-yl ester

There total 3 articles about Acetic acid (2R,3R,4R,5R,6S)-4,5-diacetoxy-2-(5-bromomethyl-2-methoxy-phenyl)-6-methyl-tetrahydro-pyran-3-yl 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: 65.0%

4-methoxy-3-(2,3,4-tri-O-acetyl-β-L-fucopyranosyl)toluene (189135-52-2) → Acetic acid (2R,3R,4R,5R,6S)-4,5-diacetoxy-2-(5-bromomethyl-2-methoxy-phenyl)-6-methyl-tetrahydro-pyran-3-yl ester (263148-79-4)

Guidance literature:

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane;

DOI:10.1055/s-1999-2738

Reference yield:

p-methylanizole (104-93-8) → Acetic acid (2R,3R,4R,5R,6S)-4,5-diacetoxy-2-(5-bromomethyl-2-methoxy-phenyl)-6-methyl-tetrahydro-pyran-3-yl ester (263148-79-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / SnCl₄, silver trifluoroacetate / CH₂Cl₂

2: 65 percent / NBS, AIBN / CCl₄

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); silver trifluoroacetate; tin(IV) chloride; In tetrachloromethane; dichloromethane;

DOI:10.1055/s-1999-2738

Reference yield:

1,2,3,4-tetra-O-acetyl-β-L-fucopyranose (7404-35-5,17081-04-8,20853-37-6,24332-95-4,27821-10-9,27821-11-0,30021-94-4,33947-15-8,34371-40-9,34371-41-0,35521-79-0,36807-81-5,36807-82-6,50615-78-6,51921-33-6,62182-03-0,64913-16-2,70004-81-8,84622-47-9,87303-56-8,108942-32-1,108942-33-2,109430-94-6,143394-72-3) → Acetic acid (2R,3R,4R,5R,6S)-4,5-diacetoxy-2-(5-bromomethyl-2-methoxy-phenyl)-6-methyl-tetrahydro-pyran-3-yl ester (263148-79-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / SnCl₄, silver trifluoroacetate / CH₂Cl₂

2: 65 percent / NBS, AIBN / CCl₄

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); silver trifluoroacetate; tin(IV) chloride; In tetrachloromethane; dichloromethane;

DOI:10.1055/s-1999-2738

upstream raw materials:

4-methoxy-3-(2,3,4-tri-O-acetyl-β-L-fucopyranosyl)toluene

p-methylanizole

1,2,3,4-tetra-O-acetyl-β-L-fucopyranose

Downstream raw materials:

(2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-{2,4-dimethoxy-5-[4-methoxy-3-((2R,3R,4R,5R,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yl)-benzyl]-phenyl}-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

(2S,4S,5R,6R)-5-Acetylamino-2-{2,4-dimethoxy-5-[4-methoxy-3-((2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yl)-benzyl]-phenyl}-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

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