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

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5R)-4,5-diacetoxy-6-bromo-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester
• CAS No.: 59202-80-1
• Molecular Formula: C₁₉H₂₃BrO₁₀S
• Molecular Weight: 523.356
• Mol file: 59202-80-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about Acetic acid (2R,3R,4S,5R)-4,5-diacetoxy-6-bromo-2-(toluene-4-sulfonyloxymethyl)-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: 99.0%

1,2,3,4-tetra-O-acetyl-6-O-deoxy-6-tosyl-α/β-D-mannopyranose (78478-66-7) → 2,3,4-tri-O-acetyl-6-O-(p-toluenesulfonyl)-α-D-mannopyranosyl bromide (13046-90-7,55500-08-8,59202-80-1,139757-70-3,136846-18-9)

Guidance literature:

With hydrogen bromide; In acetic acid; at 0 ℃; for 2h;

DOI:10.1016/j.tetlet.2007.01.128

Reference yield:

D-Mannose (530-26-7) → 2,3,4-tri-O-acetyl-6-O-(p-toluenesulfonyl)-α-D-mannopyranosyl bromide (13046-90-7,55500-08-8,59202-80-1,139757-70-3,136846-18-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / pyridine / 5 h / -5 °C

2: pyridine / 0 °C

3: 99 percent / HBr / acetic acid / 2 h / 0 °C

With pyridine; hydrogen bromide; In acetic acid;

DOI:10.1016/j.tetlet.2007.01.128

Reference yield:

6-O-p-toluenesulfonyl-D-mannopyranose (6619-07-4,26391-80-0,121363-57-3,121363-64-2,121363-65-3,121363-70-0) → 2,3,4-tri-O-acetyl-6-O-(p-toluenesulfonyl)-α-D-mannopyranosyl bromide (13046-90-7,55500-08-8,59202-80-1,139757-70-3,136846-18-9)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 0 °C

2: 99 percent / HBr / acetic acid / 2 h / 0 °C

With pyridine; hydrogen bromide; In acetic acid;

DOI:10.1016/j.tetlet.2007.01.128

upstream raw materials:

1,2,3,4-tetra-O-acetyl-6-O-deoxy-6-tosyl-α/β-D-mannopyranose

D-Mannose

6-O-p-toluenesulfonyl-D-mannopyranose

p-toluenesulfonyl chloride

Downstream raw materials:

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

2,3,4-tri-O-acetyl-1-S-methylsulfonyl-6-O-(4-methylphenylsulfonyl)-1-thio-β-D-glucose

2,3,4-tri-O-acetyl-1,5-anhydro-6-O-(4-methylphenylsulfonyl)-D-arabino-hex-1-enitol

(2,3,4-tri-O-acetyl-6-azido-α-D-mannopyranosyl)-(1->2)-carboxymethyl-3,4-di-O-benzoyl-6-azido-α-D-mannopyranose