1-Thio-beta-D-glucose pentaacetate

Base Information

• Chemical Name: 1-Thio-beta-D-glucose pentaacetate
• CAS No.: 13639-50-4
• Molecular Formula: C₁₆H₂₂O₁₀S
• Molecular Weight: 406.411
• Hs Code.: 2938909090
• European Community (EC) Number: 237-128-3
• Nikkaji Number: J277.966H
• Mol file: 13639-50-4.mol

Synonyms:1-Thio-beta-D-glucose pentaacetate;13639-50-4;EINECS 237-128-3;[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-acetylsulfanyloxan-2-yl]methyl acetate;2,3,4,6-tetra-O-acetyl-1-S-acetyl-1-thiohexopyranose;C16H22O10S;C16-H22-O10-S;.beta.-D-Glucopyranose, 1-thio-, pentaacetate;SCHEMBL5799586;NSC 409737;1-Thio-beta-D-glucopyranose pentaacetate;CS-0113409;E81413;(2R,3R,4S,5R,6S)-2-(Acetoxymethyl)-6-(acetylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Chemical Property of 1-Thio-beta-D-glucose pentaacetate

Chemical Property:

• Boiling Point: 468.1°Cat760mmHg
• Flash Point: 222.3°C
• PSA: 156.80000
• Density: 1.32g/cm³
• LogP: 0.34920
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 11
• Exact Mass: 406.09336807
• Heavy Atom Count: 27
• Complexity: 604

Purity/Quality:

98%min ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)SC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)SC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C

Technology Process of 1-Thio-beta-D-glucose pentaacetate

There total 34 articles about 1-Thio-beta-D-glucose pentaacetate 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

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

C₂₁H₂₈N₂O₁₁S₂

C₂₂H₃₀N₂O₁₁S₂