.beta.-D-Glucopyranose, 1,1-dithiobis1-deoxy-, octaacetate

Base Information

• Chemical Name: .beta.-D-Glucopyranose, 1,1-dithiobis1-deoxy-, octaacetate
• CAS No.: 5207-08-9
• Molecular Formula: C28H38O18S2
• Molecular Weight: 726.731
• Mol file: 5207-08-9.mol

Synonyms:.beta.-D-Glucopyranose, 1,1-dithiobis1-deoxy-, octaacetate

Chemical Property of .beta.-D-Glucopyranose, 1,1-dithiobis1-deoxy-, octaacetate

Chemical Property:

• PSA: 279.46000
• LogP: 0.53400

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of .beta.-D-Glucopyranose, 1,1-dithiobis1-deoxy-, octaacetate

There total 6 articles about .beta.-D-Glucopyranose, 1,1-dithiobis1-deoxy-, octaacetate 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: 56.0%

tetraacetyl thioglucose (19879-84-6) + [(4,5-bis(diphenylphosphino)-9,9-dimethylxanthene)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate → (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((2'-amino-[1,1'-biphenyl]-2-yl)thio)tetrahydro-2H-pyran-3,4,5-triyltriacetate + 9H-carbazole (86-74-8,105184-46-1,97960-57-1) + bis(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)disulfide (5207-08-9)

Guidance literature:

With triethylamine; In tetrahydrofuran; water; at 25 ℃; for 1h; Sealed tube; Schlenk technique; Inert atmosphere;

DOI:10.1002/asia.201701415

Reference yield:

tetraacetyl thioglucose (19879-84-6) + 3,4,6-tri-O-acetyl-D-glucal (52485-06-0) + acetic anhydride (108-24-7) → 3,4,6-tri-O-acetyl-1,5-anhydro-2-thio-2-S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-D-altritol (1356155-30-0) + bis(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)disulfide (5207-08-9) + O2,O3,O4,O6,S-Pentaacetyl-1-thio-β-D-glucopyranose (6806-56-0,13639-50-4,51898-27-2,62860-10-0,63783-77-7,92217-67-9,92217-68-0,130796-15-5)

Guidance literature:

tetraacetyl thioglucose; 3,4,6-tri-O-acetyl-D-glucal; With 2,2-dimethoxy-2-phenylacetophenone; In ethanol; dichloromethane; at 20 ℃; for 1h; UV-irradiation;

acetic anhydride; With pyridine; at 20 ℃; for 2h; optical yield given as %de; regioselective reaction;

DOI:10.1016/j.tetlet.2011.11.140

Reference yield:

tetraacetyl thioglucose (19879-84-6) + 3,4,6-tri-O-acetyl-D-galactal (6586-65-8) + acetic anhydride (108-24-7) → C26H36O16S (1356155-31-1) + bis(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)disulfide (5207-08-9) + O2,O3,O4,O6,S-Pentaacetyl-1-thio-β-D-glucopyranose (6806-56-0,13639-50-4,51898-27-2,62860-10-0,63783-77-7,92217-67-9,92217-68-0,130796-15-5)

Guidance literature:

tetraacetyl thioglucose; 3,4,6-tri-O-acetyl-D-galactal; With 2,2-dimethoxy-2-phenylacetophenone; In ethanol; dichloromethane; at 20 ℃; for 1h; UV-irradiation;

acetic anhydride; With pyridine; at 20 ℃; for 2h; optical yield given as %de; regioselective reaction;

DOI:10.1016/j.tetlet.2011.11.140

upstream raw materials:

tetraacetyl thioglucose

3,4,6-tri-O-acetyl-D-glucal

acetic anhydride

3,4,6-tri-O-acetyl-D-galactal

Downstream raw materials:

O²,O³,O⁴,O⁶,S-Pentaacetyl-1-thio-β-D-glucopyranose

O²,O³,O⁴,O⁶-Tetraacetyl-1-thio-D-glucose

O²,O³,O⁴,O⁶-Tetraacetyl-O¹-benzoyl-β-D-glucopyranose

N-phenyl-S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)sulfenamide

Refernces

• 1、 Staderini, Samuele,Chambery, Angela,Marra, Alberto,Dondoni, Alessandro. "Free-radical hydrothiolation of glycals: A thiol-ene-based synthesis of S-disaccharides". supporting information; experimental part. p. 702 - 704. Retrieved 2012/02/15.