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

Base Information

• Chemical Name: phenyl 3,6-di-O-benzyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
• CAS No.: 254444-23-0
• Molecular Formula: C₄₈H₄₉NO₁₅S
• Molecular Weight: 911.981
• Mol file: 254444-23-0.mol

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

Chemical Property of phenyl 3,6-di-O-benzyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-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 3,6-di-O-benzyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

There total 2 articles about phenyl 3,6-di-O-benzyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-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: 71.0%

2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate (86520-63-0) + phenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (159734-70-0) → phenyl 3,6-di-O-benzyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (254444-23-0) + C48H49NO14S

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -20 ℃; for 2h; Temperature; stereoselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1002/asia.201801486

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) + benzyl bromide (100-39-0) + 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 3,6-di-O-benzyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (254444-23-0) + C48H49NO14S

Guidance literature:

Multi-step reaction with 2 steps

1.1: toluene-4-sulfonic acid / 20 °C / Inert atmosphere

1.2: 0 - 20 °C

2.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / -20 °C / Molecular sieve; Inert atmosphere

With trimethylsilyl trifluoromethanesulfonate; toluene-4-sulfonic acid; In dichloromethane;

DOI:10.1002/asia.201801486

Reference yield: 62.0%

phenyl 3,6-di-O-benzyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (254444-23-0) → C32H39NO9S

Guidance literature:

With hydrazine hydrate; In methanol; at 70 ℃; for 2h;

DOI:10.1002/cbic.201300537

upstream raw materials:

benzaldehyde dimethyl acetal

benzyl bromide

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

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