2,3,4,6-Tetra-O-acetyl-1-S-acetyl-1-thio-a-D-galactopyranoside

Base Information

• Chemical Name: 2,3,4,6-Tetra-O-acetyl-1-S-acetyl-1-thio-a-D-galactopyranoside
• CAS No.: 130796-15-5
• Molecular Formula: C16H22O10S
• Molecular Weight: 406.411
• Mol file: 130796-15-5.mol

Synonyms:1,2,3,4,6-Penta-O-acetyl-a-D-thiogalactopyranose;2,3,4,6-Tetra-O-acetyl-1-S-acetyl-1-thio-α-D-galactopyranoside

Chemical Property of 2,3,4,6-Tetra-O-acetyl-1-S-acetyl-1-thio-a-D-galactopyranoside

Chemical Property:

• Melting Point: 95°C
• Refractive Index: 1.509
• Boiling Point: 468.1±45.0 °C(Predicted)
• PSA: 156.80000
• Density: 1.32±0.1 g/cm3(Predicted)
• LogP: 0.34920
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

95% ^*data from raw suppliers

1,2,3,4,6-Penta-O-acetyl-a-D-thiogalactopyranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2,3,4,6-Tetra-O-acetyl-1-S-acetyl-1-thio-a-D-galactopyranoside is used in the synthesis and evaluation for iNKT stimulation of α-S-galactosylceramide. Used in the synthesis and evaluation for iNKT stimulation of α-S-galactosylceramide.

Technology Process of 2,3,4,6-Tetra-O-acetyl-1-S-acetyl-1-thio-a-D-galactopyranoside

There total 42 articles about 2,3,4,6-Tetra-O-acetyl-1-S-acetyl-1-thio-a-D-galactopyranoside 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: 98.0%

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) + potassium thioacetate (10387-40-3) → 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:

for 2h; Neat (no solvent); Ball milling;

DOI:10.1039/b904454j

Reference yield: 97.0%

tiolacetic acid (507-09-5) + β-D-glucose pentaacetate (604-69-3) → 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:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 30 ℃; for 3.5h; stereoselective reaction; Inert atmosphere;

DOI:10.1039/d0ob01956a

Reference yield: 95.0%

potassium thioacetate (10387-40-3) + β-D-glucose pentaacetate (604-69-3) → 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:

With boron trifluoride diethyl etherate; In ethyl acetate; at 50 ℃; for 4h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; Schlenk technique;

DOI:10.1002/ejoc.202100357

upstream raw materials:

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

acetic anhydride

bis(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)disulfide

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

Downstream raw materials:

Sodium; (2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-thiolate

1-thio-β-D-glucopyranose

sodium salt of 1-thio-α-D-glucopyranose

N-(2,4-dimethoxybenzyl)-1-S-(2,3,4,6-tetra-O-acetyl)-D-glucopyranosylsulfenamide

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