1,2,4,6-tetra-O-benzoyl-3-O-(bromoacetyl)-β-D-glucopyranose

Base Information

• Chemical Name: 1,2,4,6-tetra-O-benzoyl-3-O-(bromoacetyl)-β-D-glucopyranose
• CAS No.: 146530-54-3
• Molecular Formula: C₃₆H₂₉BrO₁₁
• Molecular Weight: 717.524
• Mol file: 146530-54-3.mol

Synonyms:1,2,4,6-tetra-O-benzoyl-3-O-(bromoacetyl)-β-D-glucopyranose

Chemical Property of 1,2,4,6-tetra-O-benzoyl-3-O-(bromoacetyl)-β-D-glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2,4,6-tetra-O-benzoyl-3-O-(bromoacetyl)-β-D-glucopyranose

There total 1 articles about 1,2,4,6-tetra-O-benzoyl-3-O-(bromoacetyl)-β-D-glucopyranose 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: 80.0%

1,2,4,6-tetra-O-benzoyl-β-D-glucopyranoside (72076-17-6) + 2-Bromoacetyl bromide (598-21-0) → 1,2,4,6-tetra-O-benzoyl-3-O-(bromoacetyl)-β-D-glucopyranose (146530-54-3)

Guidance literature:

With 2,4,6-trimethyl-pyridine; In dichloromethane; for 3h; Ambient temperature;

DOI:10.1021/jo00057a021

Reference yield: 81.0%

1,2,4,6-tetra-O-benzoyl-3-O-(bromoacetyl)-β-D-glucopyranose (146530-54-3) → 2,4,6-tri-O-benzoyl-3-O-(bromoacetyl)-β-D-glucopyranosyl bromide

Guidance literature:

With hydrogen bromide; acetic acid; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1021/jo00057a021

Reference yield:

1,2,4,6-tetra-O-benzoyl-3-O-(bromoacetyl)-β-D-glucopyranose (146530-54-3) → (2S,4aR,6S,7R,8R,8aR)-6-[(2R,3R,4S,5R,6R)-2-(5-Benzyloxycarbonylamino-pentyloxy)-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-7-hydroxy-8-methoxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester (1054630-28-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 81 percent / 30 percent HBr/ acetic acid / CH₂Cl₂ / 1 h / Ambient temperature

2: 83 percent / 2,4,6-trimethylpyridine, AgOTf, 3-Angstroem molecular sieves / CH₂Cl₂ / 0.17 h / 0 °C

3: 1) TMSOTf, 2) pyridine / 1) CH₂Cl₂, -20 deg C, 1 h, 2) RT, 16 h

4: NaOMe / methanol / 24 h / Ambient temperature

With pyridine; 2,4,6-trimethyl-pyridine; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; hydrogen bromide; sodium methylate; silver trifluoromethanesulfonate; acetic acid; In methanol; dichloromethane;

DOI:10.1021/jo00057a021

upstream raw materials:

1,2,4,6-tetra-O-benzoyl-β-D-glucopyranoside

2-Bromoacetyl bromide

Downstream raw materials:

(2S,4aR,6S,7R,8R,8aR)-6-[(2R,3R,4S,5R,6R)-2-(5-Benzyloxycarbonylamino-pentyloxy)-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-7-hydroxy-8-methoxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid

(2S,4aR,6S,7R,8R,8aR)-6-[(2R,3R,4S,5R,6R)-2-(5-Benzyloxycarbonylamino-pentyloxy)-3,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy]-7-hydroxy-8-methoxy-2-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester

5-<(benzyloxycarbonyl)amino>pentyl 2,4,6-tri-O-benzoyl-3-O-(bromoacetyl)-β-D-glucopyranoside