phenyl 6-O-benzoyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl 6-O-benzoyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
• CAS No.: 181023-17-6
• Molecular Formula: C₂₇H₂₃NO₇S
• Molecular Weight: 505.548
• Mol file: 181023-17-6.mol

Synonyms:phenyl 6-O-benzoyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Chemical Property of phenyl 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 6-O-benzoyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

There total 2 articles about phenyl 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: 86.0%

benzoyl chloride (98-88-4) + 2-((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione (136882-36-5,79528-50-0) → phenyl 6-O-benzoyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (181023-17-6)

Guidance literature:

With dimethyltin dichloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 2.5h;

DOI:10.1002/asia.201801486

Reference yield:

phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (79528-49-7) → phenyl 6-O-benzoyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (181023-17-6)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOMe, MeOH / 2 h / Ambient temperature

2: 1.) (Bu₃Sn)2O / 1.) toluene, reflux, 15 h, 2.) toluene, RT, 5 h

With methanol; sodium methylate; bis(tri-n-butyltin)oxide;

DOI:10.1016/S0957-4166(98)00246-8

Reference yield: 70.0%

phenyl 6-O-benzoyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (181023-17-6) + 2,3,4,6-tetra-O-acetyl-β-galactopyranosyl fluoride (4163-45-5) → phenyl 6-O-benzoyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside (181023-18-7)

Guidance literature:

With 4 A molecular sieve; silver trifluoromethanesulfonate; tin(ll) chloride; In dichloromethane; toluene; at -15 - 20 ℃; for 2h;

DOI:10.1016/S0957-4166(98)00246-8

upstream raw materials:

benzoyl chloride

2-((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione

phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Downstream raw materials:

phenyl 6-O-benzoyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside

N-[(2R,3R,4R,5S,6R)-6-Hydroxymethyl-2-methoxy-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-4-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide

methyl 6-O-benzoyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside

methyl 6-O-benzoyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-3-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside