1,2,3,4,6-Penta-O-acetyl-1-thio-beta-D-galactopyranose

Base Information

• Chemical Name: 1,2,3,4,6-Penta-O-acetyl-1-thio-beta-D-galactopyranose
• CAS No.: 6806-56-0
• Molecular Formula: C16H22 O10 S
• Molecular Weight: 406.411
• NSC Number: 409737,89877
• DSSTox Substance ID: DTXSID70929370
• Mol file: 6806-56-0.mol

Synonyms:6806-56-0;1,2,3,4,6-Penta-O-acetyl-1-thio-beta-D-galactopyranose;2,3,4,6-tetra-O-acetyl-1-S-acetyl-1-thiohexopyranose;NSC89877;Glucopyranose deriv.;Oprea1_802175;DTXSID70929370;NSC-89877;NSC409737;STK669717;AKOS005591985;NSC-409737;FT-0674883;.alpha.-D-Glucopyranose, 1-thio-, pentaacetate;2,3,4,6-Tetra-O-acetyl-1-S-acetyl-1-thio-.alpha.-D-glucopyranose;(3,4,5-triacetoxy-6-acetylsulfanyl-tetrahydropyran-2-yl)methyl acetate;3,5-BIS(ACETYLOXY)-2-[(ACETYLOXY)METHYL]-6-(ACETYLSULFANYL)TETRAHYDRO-2H-PYRAN-4-YL ACETATE

Chemical Property of 1,2,3,4,6-Penta-O-acetyl-1-thio-beta-D-galactopyranose

Chemical Property:

• 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:

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

Technology Process of 1,2,3,4,6-Penta-O-acetyl-1-thio-beta-D-galactopyranose

There total 37 articles about 1,2,3,4,6-Penta-O-acetyl-1-thio-beta-D-galactopyranose 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

methyl 2,3,6-tri-O-benzyl-4-deoxy-α-L-threo-hex-4-enopyranoside

methyl 2,3,6-tri-O-benzyl-4-S-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-4-thio-β-D-glucopyranoside