.beta.-D-Glucopyranoside, 2,3,4,6-tetra-O-acetyl-.beta.-D-glucopyranosyl 1-thio-, tetraacetate

Base Information

• Chemical Name: .beta.-D-Glucopyranoside, 2,3,4,6-tetra-O-acetyl-.beta.-D-glucopyranosyl 1-thio-, tetraacetate
• CAS No.: 5505-45-3
• Molecular Formula: C₂₈H₃₈O₁₈S
• Molecular Weight: 694.665
• Mol file: 5505-45-3.mol

Synonyms:.beta.-D-Glucopyranoside, 2,3,4,6-tetra-O-acetyl-.beta.-D-glucopyranosyl 1-thio-, tetraacetate

Chemical Property of .beta.-D-Glucopyranoside, 2,3,4,6-tetra-O-acetyl-.beta.-D-glucopyranosyl 1-thio-, tetraacetate

Chemical Property:

• PSA: 254.16000
• LogP: -0.11420

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of .beta.-D-Glucopyranoside, 2,3,4,6-tetra-O-acetyl-.beta.-D-glucopyranosyl 1-thio-, tetraacetate

There total 19 articles about .beta.-D-Glucopyranoside, 2,3,4,6-tetra-O-acetyl-.beta.-D-glucopyranosyl 1-thio-, tetraacetate 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%

1-thio-α,α-trehalose (17317-98-5,18977-84-9,68667-06-1,68778-86-9,68778-87-0,68778-88-1,108392-13-8,62853-32-1,80441-61-8) + acetic anhydride (108-24-7) → 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-glucopyranoside (5505-45-3,18968-43-9,18968-44-0,62853-33-2,65058-34-6,68736-77-6,68736-78-7,68736-79-8,68736-80-1,103189-12-4,120331-62-6)

Guidance literature:

With pyridine; at 20 ℃;

DOI:10.1016/j.tetlet.2012.05.159

Reference yield: 93.0%

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside (5505-45-3)

Guidance literature:

With sodium sulfide; sodium hydrogen sulfate; tetrabutylammomium bromide; In water; benzene; for 0.25h; Heating;

DOI:10.1016/S0008-6215(00)90766-3

Reference yield: 86.0%

tetraacetyl thioglucose (19879-84-6) + β-D-glucose pentaacetate (604-69-3) → (2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside (65058-34-6) + 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside (5505-45-3)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 18h; optical yield given as %de; Inert atmosphere;

DOI:10.1016/j.carres.2009.03.017

upstream raw materials:

2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl thiocyanate

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

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

thiourea

Downstream raw materials:

1-thio-α,α-trehalose

D-glycopyranosyl β-D-thioglucopyranoside