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

Base Information

• Chemical Name: phenyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1→4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside
• CAS No.: 130130-52-8
• Molecular Formula: C₃₀H₃₈O₁₆S
• Molecular Weight: 686.688
• Mol file: 130130-52-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about phenyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1→4)-2,3,6-tri-O-acetyl-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:

C24H34O17 + thiophenol (108-98-5) → phenyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1→4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside (130130-52-8)

Guidance literature:

With boron trifluoride diethyl etherate; at 0 - 20 ℃;

DOI:10.1039/c6ra23198e

Reference yield:

2,3-di-O-acetyl-1,6-anhydro-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glycopyranose (28868-67-9) + phenylthiotrimethylsilane (4551-15-9) → phenyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1→4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside (130130-52-8)

Guidance literature:

With tetrabutyl ammonium fluoride; zinc(II) iodide; Yield given. Multistep reaction; 1.) CH₂Cl₂, RT, 21 h, 2.) THF, RT, 20 min;

DOI:10.1016/0008-6215(94)90006-X

Reference yield: 85.0%

phenyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl-(1→4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside (130130-52-8) + tert-butylchlorodiphenylsilane (58479-61-1) → Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-phenylsulfanyl-5-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 3h; Ambient temperature;

upstream raw materials:

2,3-di-O-acetyl-1,6-anhydro-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glycopyranose

phenylthiotrimethylsilane

thiophenol

Downstream raw materials:

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

2L-2,4/3-3,4-diacetyloxy-2-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyloxy)-cyclohex-5-enone

phenyl 2,3-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-6-deoxy-1-thio-β-D-xylo-hexo-5-enopyranoside

Acetic acid (2S,3R,4S,5S,6S)-3-acetoxy-6-iodomethyl-2-phenylsulfanyl-5-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester