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

Base Information

• Chemical Name: 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
• CAS No.: 492440-48-9
• Molecular Formula: C₅₃H₅₇NO₂₃S
• Molecular Weight: 1108.09
• Mol file: 492440-48-9.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 18 articles about 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 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%

2,3,4,6-tetra-O-acetyl-D-galactopyranosyl trichloroacetimidate (74808-10-9,86520-63-0,87119-53-7,92052-29-4,121238-27-5,142831-80-9,127061-80-7) + phenyl 2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)-6-O-benzoyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (492440-47-8) → 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)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In diethyl ether; dichloromethane; at 0 ℃;

DOI:10.1016/S0957-4166(02)00480-9

Reference yield: 42.0%

2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate (86520-63-0) + phenyl 2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)-6-O-benzoyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (492440-47-8) → 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)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In diethyl ether; dichloromethane; at 0 ℃; Inert atmosphere;

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) → 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)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 90 percent / Et₃N / dimethylformamide / 0 - 20 °C

2.1: Me₃SiI / CH₂Cl₂ / 0.33 h / 20 °C

2.2: 2,6-di-tert-butylpyridine / CH₂Cl₂ / 20 °C

2.3: MeOH / CH₂Cl₂ / 0.5 h / 20 °C

3.1: 0.32 g / pyridine / 20 °C

4.1: 83 percent / EtSH; BF₃*Et₂O / CH₂Cl₂ / 20 °C

5.1: 95 percent / Et₃N / acetonitrile / -40 °C

6.1: 80 percent / TMSOTf / diethyl ether; CH₂Cl₂ / 0 °C

With pyridine; trimethylsilyl iodide; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; triethylamine; ethanethiol; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0957-4166(02)00480-9

upstream raw materials:

2,3,4,6-tetra-O-acetyl-D-galactopyranosyl trichloroacetimidate

phenyl 2,3,4-tri-O-acetyl-α-L-fucopyranosyl-(1->3)-6-O-benzoyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

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

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

Downstream raw materials:

11-bromo-undecyl 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

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

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

11-acetylsulfanyl-undecyl 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