phenyl 6-O-(2-amino-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-2-azido-4-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside

Base Information

• Chemical Name: phenyl 6-O-(2-amino-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-2-azido-4-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside
• CAS No.: 548486-23-3
• Molecular Formula: C₃₂H₃₆N₄O₈S
• Molecular Weight: 636.726
• Mol file: 548486-23-3.mol

Synonyms:phenyl 6-O-(2-amino-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-2-azido-4-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside

Chemical Property of phenyl 6-O-(2-amino-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-2-azido-4-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 6-O-(2-amino-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-2-azido-4-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside

There total 8 articles about phenyl 6-O-(2-amino-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-2-azido-4-O-benzyl-2-deoxy-1-thio-α-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: 95.0%

phenyl 3-O-acetyl-6-O-(3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-phtalimido-β-D-glucopyranosyl)-2-azido-4-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside (548486-13-1) → phenyl 6-O-(2-amino-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-2-azido-4-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside (548486-23-3)

Guidance literature:

With hydrazine hydrate; In ethanol; at 90 ℃; for 20h;

DOI:10.1021/ol048746f

Reference yield: 91.0%

phenyl 3-O-acetyl-6-O-(4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-2-azido-4-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside → phenyl 6-O-(2-amino-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-2-azido-4-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside (548486-23-3)

Guidance literature:

With ethylenediamine; In butan-1-ol; Heating;

DOI:10.1016/j.bmc.2007.05.012

Reference yield:

phenylthiotrimethylsilane (4551-15-9) → phenyl 6-O-(2-amino-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-2-azido-4-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside (548486-23-3)

Guidance literature:

Multi-step reaction with 4 steps

1: ZnI₂ / 1,2-dichloro-ethane / 16 h

2: 1.15 g / aq. TFA / CH₂Cl₂ / 0.17 h / 20 °C

3: 83 percent / AgOTf; K₂CO₃; MS 4 Angstroem / CH₂Cl₂ / 2 h

4: 91 percent / ethylenediamine / butan-1-ol / 20 h / 90 °C

With MS 4 Angstroem; silver trifluoromethanesulfonate; potassium carbonate; ethylenediamine; trifluoroacetic acid; zinc(II) iodide; In dichloromethane; 1,2-dichloro-ethane; butan-1-ol;

DOI:10.1021/ja029316s

upstream raw materials:

phenyl 3-O-acetyl-6-O-(3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-phtalimido-β-D-glucopyranosyl)-2-azido-4-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside

phenylthiotrimethylsilane

phenyl 3-O-acetyl-2-azido-4-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside

phenyl 3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-1-seleno-β-D-glucopyranoside

Downstream raw materials:

phenyl 2-amino-4-O-benzyl-6-O-{4,6-O-benzylidene-2-deoxy-2-[(R)-3-octacosanoyloxy-hexadecan]amido-β-D-glucopyranosyl}-2-deoxy-1-thio-α-D-glucopyranoside

4-oxo-pentanoic acid 1-({6-[3-benzyloxy-5-(3-benzyloxy-hexadecanoylamino)-4-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethoxy]-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ylcarbamoyl}-methyl)-tetradecyl ester

phenyl 2-amino-4-O-benzyl-6-O-{4,6-O-benzylidene-2-deoxy-2-[(R)-3-levulinoyloxyhexadecanoylamino]-β-D-glucopyranosyl}-2-deoxy-1-thio-α-D-glucopyranoside

phenyl 2-azido-4-O-benzyl-6-O-{4,6-O-benzylidene-2-deoxy-2-[(R)-3-levulinoyloxyhexadecanoylamino]-β-D-glucopyranosyl}-2-deoxy-1-thio-α-D-glucopyranoside