phenyl 4,6-O-benzylidene-1-thio-β-D-glucosaminopyranoside

Base Information

• Chemical Name: phenyl 4,6-O-benzylidene-1-thio-β-D-glucosaminopyranoside
• CAS No.: 1394857-30-7
• Molecular Formula: C₁₉H₂₁NO₄S
• Molecular Weight: 359.446
• Mol file: 1394857-30-7.mol

Synonyms:phenyl 4,6-O-benzylidene-1-thio-β-D-glucosaminopyranoside

Chemical Property of phenyl 4,6-O-benzylidene-1-thio-β-D-glucosaminopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 4,6-O-benzylidene-1-thio-β-D-glucosaminopyranoside

There total 6 articles about phenyl 4,6-O-benzylidene-1-thio-β-D-glucosaminopyranoside 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: 99.0%

C21H20Cl3NSO5 → phenyl 4,6-O-benzylidene-1-thio-β-D-glucosaminopyranoside (1394857-30-7)

Guidance literature:

With water; potassium hydroxide; In tetrahydrofuran; methanol; for 2h;

DOI:10.1021/jo300722y

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroacetamido)-β-D-glucopyranose (56644-75-8,10353-00-1) → phenyl 4,6-O-benzylidene-1-thio-β-D-glucosaminopyranoside (1394857-30-7)

Guidance literature:

Multi-step reaction with 4 steps

1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 18 h / 20 °C / Inert atmosphere

2: methanol; sodium / Inert atmosphere

3: camphorsulfonic acid / tetrahydrofuran / 2 h / Dean-Stark; Reflux

4: potassium hydroxide; water / tetrahydrofuran; methanol / 2 h

With methanol; trimethylsilyl trifluoromethanesulfonate; camphorsulfonic acid; water; sodium; potassium hydroxide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo300722y

Reference yield:

phenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-trichloroacetamido-β-D-glucopyranoside (169557-87-3) → phenyl 4,6-O-benzylidene-1-thio-β-D-glucosaminopyranoside (1394857-30-7)

Guidance literature:

Multi-step reaction with 3 steps

1: methanol; sodium / Inert atmosphere

2: camphorsulfonic acid / tetrahydrofuran / 2 h / Dean-Stark; Reflux

3: potassium hydroxide; water / tetrahydrofuran; methanol / 2 h

With methanol; camphorsulfonic acid; water; sodium; potassium hydroxide; In tetrahydrofuran; methanol;

DOI:10.1021/jo300722y

upstream raw materials:

thiophenol

(+)-D-glucosamine hydrochloride

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

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroacetamido)-β-D-glucopyranose

Downstream raw materials:

methyl [phenyl 4-O-(2-azido-3,6-O-dibenzyl-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-1-thio-β-L-ido-pyranoside]uronate

methyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-trichloroacetyl-α-D-glucopyranosyl-(1→4)-(phenyl-2-O-benzoyl-3-O-benzyl-1-thio-β-L-idopyranoside)uronate

methyl [phenyl 4-O-(2-azido-3,6-O-dibenzyl-2-deoxy-4-O-trichloroacetyl-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-1-thio-L-idopyranoside]uronate

methyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl-(1→4)-(phenyl 3-O-benzyl-2-O-benzoyl-1-thio-β-L-idopyranoside)uronate