3-bromopropanyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-[2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)]-6-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Base Information

• Chemical Name: 3-bromopropanyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-[2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)]-6-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• CAS No.: 1352746-00-9
• Molecular Formula: C₅₀H₅₈BrNO₂₄
• Molecular Weight: 1136.91
• Mol file: 1352746-00-9.mol

Synonyms:3-bromopropanyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-[2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)]-6-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Chemical Property of 3-bromopropanyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-[2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)]-6-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-bromopropanyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-[2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)]-6-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

There total 13 articles about 3-bromopropanyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-[2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)]-6-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 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: 92.0%

phenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl)-(1->3)-6-O-benzoyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (492440-48-9) + 1-bromo-3-propanol (627-18-9) → 3-bromopropanyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-[2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)]-6-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (1352746-00-9)

Guidance literature:

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -40 ℃; for 3h; Molecular sieve; Inert atmosphere;

DOI:10.1002/anie.201101055

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose (10022-13-6,31505-44-9,81704-02-1,116347-84-3,131234-07-6,144300-04-9,79733-86-1) → 3-bromopropanyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-[2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)]-6-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (1352746-00-9)

Guidance literature:

Multi-step reaction with 8 steps

1: boron trifluoride diethyl etherate / dichloromethane / Inert atmosphere

2: guanidine nitrate; guanidine nitrate / methanol; dichloromethane / Inert atmosphere

3: toluene-4-sulfonic acid / acetonitrile / Inert atmosphere

4: 2,6-di-tert-butyl-pyridine; 1-(Trimethylsilyl)imidazole / dichloromethane / Inert atmosphere

5: trifluoroacetic acid / dichloromethane; water / Inert atmosphere

6: triethylamine / acetonitrile / Inert atmosphere

7: trimethylsilyl trifluoromethanesulfonate / diethyl ether; dichloromethane / 0 °C / Inert atmosphere

8: N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 3 h / -40 °C / Molecular sieve; Inert atmosphere

With N-iodo-succinimide; 2,6-di-tert-butyl-pyridine; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; guanidine nitrate; toluene-4-sulfonic acid; guanidine nitrate; triethylamine; 1-(Trimethylsilyl)imidazole; trifluoroacetic acid; In methanol; diethyl ether; dichloromethane; water; acetonitrile;

DOI:10.1002/anie.201101055

Reference yield:

6-deoxy-L-galactose (73-34-7,87-96-7,488-79-9,551-63-3,609-01-8,643-17-4,643-18-5,4164-09-4,6014-42-2,6155-36-8,6189-71-5,6696-41-9,6736-43-2,13224-93-6,22611-09-2,28161-49-1,28161-50-4,28161-52-6,45864-36-6,63814-64-2,71116-59-1,71116-61-5,72598-05-1,87936-88-7,87936-89-8,97466-79-0,116908-82-8,120442-60-6,123484-22-0,133576-32-6) → 3-bromopropanyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-[2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)]-6-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (1352746-00-9)

Guidance literature:

Multi-step reaction with 6 steps

1: triethylamine / N,N-dimethyl-formamide / Inert atmosphere

2: 2,6-di-tert-butyl-pyridine; 1-(Trimethylsilyl)imidazole / dichloromethane / Inert atmosphere

3: trifluoroacetic acid / dichloromethane; water / Inert atmosphere

4: triethylamine / acetonitrile / Inert atmosphere

5: trimethylsilyl trifluoromethanesulfonate / diethyl ether; dichloromethane / 0 °C / Inert atmosphere

6: N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 3 h / -40 °C / Molecular sieve; Inert atmosphere

With N-iodo-succinimide; 2,6-di-tert-butyl-pyridine; trimethylsilyl trifluoromethanesulfonate; triethylamine; 1-(Trimethylsilyl)imidazole; trifluoroacetic acid; In diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/anie.201101055

upstream raw materials:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose

2,3,4,6-tetra-O-acetyl-α/β-D-galactopyranose

6-deoxy-L-galactose

D-galactose pentaacetate

Downstream raw materials:

3-thioacetylpropanyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-[2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)]-6-O-benzoyl-2-deoxy-2-phthalimido-β-D-glucopyranoside