Acetic acid (2R,3R,4S,5R)-3-acetoxy-6-bromo-5-(toluene-4-sulfonyloxy)-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5R)-3-acetoxy-6-bromo-5-(toluene-4-sulfonyloxy)-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-4-yl ester
• CAS No.: 103725-99-1
• Molecular Formula: C₂₄H₂₇BrO₁₁S₂
• Molecular Weight: 635.508

Synonyms:Acetic acid (2R,3R,4S,5R)-3-acetoxy-6-bromo-5-(toluene-4-sulfonyloxy)-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-4-yl ester

Chemical Property of Acetic acid (2R,3R,4S,5R)-3-acetoxy-6-bromo-5-(toluene-4-sulfonyloxy)-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-4-yl ester

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Technology Process of Acetic acid (2R,3R,4S,5R)-3-acetoxy-6-bromo-5-(toluene-4-sulfonyloxy)-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-4-yl ester

There total 4 articles about Acetic acid (2R,3R,4S,5R)-3-acetoxy-6-bromo-5-(toluene-4-sulfonyloxy)-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-4-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:

1,2,3,4-tetra-O-acetyl-6-O-p-tolylsulfonyl-α,β-D-glucopyranose (95118-61-9) + 3,4-di-O-acetyl-2,6-di-O-tosyl-α/β-D-glucopyranose (103042-48-4) → Acetic acid (2R,3R,4S,5R)-4,5-diacetoxy-6-bromo-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester (59202-80-1) + Acetic acid (2R,3R,4S,5R)-3-acetoxy-6-bromo-5-(toluene-4-sulfonyloxy)-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-4-yl ester (103725-99-1)

Guidance literature:

With hydrogen bromide; In acetic acid; for 24h; Yield given. Title compound not separated from byproducts; Ambient temperature;

DOI:10.1016/0008-6215(89)85126-2

Reference yield:

→ 3,4-di-O-acetyl-2,6-di-O-tosyl-α-D-glucopyranosyl bromide (103725-99-1)

Guidance literature:

With hydrogen bromide; acetic acid;

DOI:10.1002/hlca.19480310652

Reference yield:

1,3,4-tri-O-acetyl-2,6-di-O-p-tolylsulfonyl-α-D-glucopyranose (128947-68-2) → 3,4-di-O-acetyl-2,6-di-O-tosyl-α-D-glucopyranosyl bromide (103725-99-1)

Guidance literature:

With hydrogen bromide; acetic acid;

DOI:10.1002/hlca.19480310652

upstream raw materials:

1,3,4-tri-O-acetyl-2,6-di-O-p-tolylsulfonyl-α-D-glucopyranose

p-toluenesulfonyl chloride

1,2,3,4-tetra-O-acetyl-6-O-p-tolylsulfonyl-α,β-D-glucopyranose

3,4-di-O-acetyl-2,6-di-O-tosyl-α/β-D-glucopyranose

Downstream raw materials:

3,4-di-O-acetyl-2,6-di-O-tosyl-β-D-glucopyranose 1-(dibenzyl phosphate)

6-O-p-tolylsulfonyl-3,4-di-O-acetyl-D-glucal

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