Phenyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3,6-bis-O-(phenylmethyl)-1-thio-beta-D-glucopyranoside

Base Information

• Chemical Name: Phenyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3,6-bis-O-(phenylmethyl)-1-thio-beta-D-glucopyranoside
• CAS No.: 159734-70-0
• Molecular Formula: C34H31NO6S
• Molecular Weight: 581.689
• Mol file: 159734-70-0.mol

Synonyms:Phenyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3,6-bis-O-(phenylmethyl)-1-thio-beta-D-glucopyranoside

Chemical Property of Phenyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3,6-bis-O-(phenylmethyl)-1-thio-beta-D-glucopyranoside

Chemical Property:

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Phenyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3,6-bis-O-(phenylmethyl)-1-thio-beta-D-glucopyranoside

There total 8 articles about Phenyl 2-deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3,6-bis-O-(phenylmethyl)-1-thio-beta-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: 100.0%

phenyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (208644-70-6) → phenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (159734-70-0)

Guidance literature:

With 4 Angstroem MS; sodium cyanoborohydride; In tetrahydrofuran; Ambient temperature;

DOI:10.1080/07328309808002904

Reference yield: 53.0%

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-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (159734-70-0)

Guidance literature:

benzaldehyde dimethyl acetal; 2-((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione; With toluene-4-sulfonic acid; at 20 ℃; Inert atmosphere;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; Further stages;

DOI:10.1002/asia.201801486

Reference yield: 10.0%

triethylsilane (617-86-7) + phenyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (208644-70-6) → C40H45NO6SSi + phenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (159734-70-0)

Guidance literature:

With hafnium tetrakis(trifluoromethanesulfonate); In acetonitrile; at 4 ℃; for 0.5h; regioselective reaction;

DOI:10.1016/j.tetlet.2013.10.011

upstream raw materials:

phenyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

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

thiophenol

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

Downstream raw materials:

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

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

phenyl 3,6-di-O-benzyl-2-deoxy-4-O-methanesulfonyl-2-phthalimido-1-thio-β-D-glucopyranoside

phenyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranoside