phenylthio 2,3,4,6-terta hydroxy-α-D-glucopyranosyl-(1→4)-2,3,6-triylhydroxy-β-D-glucopyranoside

Base Information

• Chemical Name: phenylthio 2,3,4,6-terta hydroxy-α-D-glucopyranosyl-(1→4)-2,3,6-triylhydroxy-β-D-glucopyranoside
• CAS No.: 27891-73-2
• Molecular Formula: C₁₈H₂₆O₁₀S
• Molecular Weight: 434.464
• Mol file: 27891-73-2.mol

Synonyms:phenylthio 2,3,4,6-terta hydroxy-α-D-glucopyranosyl-(1→4)-2,3,6-triylhydroxy-β-D-glucopyranoside

Chemical Property of phenylthio 2,3,4,6-terta hydroxy-α-D-glucopyranosyl-(1→4)-2,3,6-triylhydroxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenylthio 2,3,4,6-terta hydroxy-α-D-glucopyranosyl-(1→4)-2,3,6-triylhydroxy-β-D-glucopyranoside

There total 18 articles about phenylthio 2,3,4,6-terta hydroxy-α-D-glucopyranosyl-(1→4)-2,3,6-triylhydroxy-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: 100.0%

phenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside (5346-81-6,28022-13-1,28022-14-2) → phenylthio 2,3,4,6-terta hydroxy-α-D-glucopyranosyl-(1→4)-2,3,6-triylhydroxy-β-D-glucopyranoside (27891-73-2)

Guidance literature:

With methanol; sodium methylate;

DOI:10.1055/s-2000-7601

Reference yield:

1,2,3,6,2',3',4',6'-octa-O-acetylmaltose (3616-19-1,5328-50-7,5346-90-7,6291-42-5,6920-00-9,20764-63-0,20880-65-3,22352-19-8,23973-20-8,32447-69-1,34213-32-6,52554-32-2,53956-64-2,56907-29-0,56994-12-8,56994-13-9,57128-38-8,67650-36-6,68036-17-9,68036-19-1,78215-50-6,78215-51-7,79549-48-7,80446-82-8,85249-04-3,93221-83-1,93779-27-2,111407-83-1,111407-84-2,111407-85-3,120328-65-6,123809-59-6,132341-46-9,132341-47-0,132341-49-2,145307-94-4,20880-60-8) → phenylthio 2,3,4,6-terta hydroxy-α-D-glucopyranosyl-(1→4)-2,3,6-triylhydroxy-β-D-glucopyranoside (27891-73-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / ZnI₂ / 1,2-dichloro-ethane / 20 °C

2: MeONa / methanol / 4 h / 20 °C

With sodium methylate; zinc(II) iodide; In methanol; 1,2-dichloro-ethane;

DOI:10.1021/jo025887r

Reference yield:

α-hepta-O-acetylmaltosyl bromide (4753-07-5,5160-10-1,14206-57-6,14227-66-8,14257-35-3,67650-37-7,68682-05-3,69308-57-2,69349-74-2,70223-96-0,70223-97-1,71276-38-5,85248-99-3,118493-15-5,120575-76-0,42385-75-1) → phenylthio 2,3,4,6-terta hydroxy-α-D-glucopyranosyl-(1→4)-2,3,6-triylhydroxy-β-D-glucopyranoside (27891-73-2)

Guidance literature:

Multi-step reaction with 2 steps

1: Bu₄NHSO₄; aq. Na₂CO₃ / ethyl acetate / 0.25 h / 20 °C

2: NaOMe / methanol / 2 h

With sodium methylate; tetra(n-butyl)ammonium hydrogensulfate; sodium carbonate; In methanol; ethyl acetate;

DOI:10.1016/S0008-6215(02)00408-1

upstream raw materials:

phenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside

α-hepta-O-acetylmaltosyl bromide

thiophenol

phenylthiotrimethylsilane

Downstream raw materials:

phenyl 4-O-(4,6-O-benzylidene-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside

phenyl 6,6'-di-O-tert-butyldimethylsilyl-1-thio-β-D-maltoside

Phenyl 2,3,6-tri-O-acetyl-4-O-(2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glycopyranosyl)-1-thio-β-D-glucopyranoside

phenyl 2,3-di-O-benzyl-6-deoxy-4-O-(2,3,4-tri-O-benzyl-6-deoxy-α-D-xylo-hex-5-enopyranosyl)-1-thio-β-D-xylo-hex-5-enopyranoside