2-Propynyl-2,3,4,6-tetra-O-acetyl-b-D-glucopyranoside

Base Information

• Chemical Name: 2-Propynyl-2,3,4,6-tetra-O-acetyl-b-D-glucopyranoside
• CAS No.: 34272-02-1
• Molecular Formula: C17H22 O10
• Molecular Weight: 386.356
• Hs Code.: 29400090
• DSSTox Substance ID: DTXSID50455607
• Nikkaji Number: J946.424G
• Wikidata: Q82277691
• Mol file: 34272-02-1.mol

Synonyms:34272-02-1;2-Propynyl-2,3,4,6-tetra-O-acetyl-b-D-glucopyranoside;[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-prop-2-ynoxyoxan-2-yl]methyl acetate;2-Propynyl-tetra-O-acetyl-beta-D-glucopyranoside;SCHEMBL5050806;DTXSID50455607;AKOS015896875;1-O-Propargyl-beta-D-glucopyranose tetraacetate;2-Propynyl-tetra-O-acetyl- beta -D-glucopyranoside;W-202401;2-Propynyl-tetra-O-acetyl-beta-D-glucopyranoside, 97%;2-Propynyl-2,3,4,6-tetra-o-acetyl-beta-d-glucopyranoside

Chemical Property of 2-Propynyl-2,3,4,6-tetra-O-acetyl-b-D-glucopyranoside

Chemical Property:

• Melting Point: 114-117 °C(lit.)
• PSA: 123.66000
• LogP: -0.28070
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 11
• Exact Mass: 386.12129689
• Heavy Atom Count: 27
• Complexity: 618

Purity/Quality:

98% ^*data from raw suppliers

2-Propynyl-2,3,4,6-tetra-O-acetyl-b-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)OCC#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)OCC#C)OC(=O)C)OC(=O)C)OC(=O)C

Technology Process of 2-Propynyl-2,3,4,6-tetra-O-acetyl-b-D-glucopyranoside

There total 19 articles about 2-Propynyl-2,3,4,6-tetra-O-acetyl-b-D-glucopyranoside 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: 97.0%

O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate (74808-10-9) + propargyl alcohol (107-19-7) → 1-O-propargyl 2,3,4,6-tetra-O-acetyl-β-D-glucose (34272-02-1)

Guidance literature:

With polyvinyl bound trisulfonate ethylaminechloride; In neat (no solvent); at 60 ℃; for 3.5h; Green chemistry;

DOI:10.1039/c5ra20300g

Reference yield: 94.0%

propargyl alcohol (107-19-7) + β-D-glucose pentaacetate (604-69-3) → 1-O-propargyl 2,3,4,6-tetra-O-acetyl-β-D-glucose (34272-02-1)

Guidance literature:

With boron trifluoride diethyl ether complex; In dichloromethane; at 0 - 20 ℃; for 24.1667h; Inert atmosphere;

DOI:10.1002/chem.201800683

Reference yield: 92.0%

propargyl alcohol (107-19-7) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 1-O-propargyl 2,3,4,6-tetra-O-acetyl-β-D-glucose (34272-02-1)

Guidance literature:

With bismuth subcarbonate; In neat (no solvent); for 1h; Molecular sieve; Milling;

DOI:10.1016/j.carres.2016.09.004

upstream raw materials:

propargyl β-D-glucopyranoside

acetic anhydride

propargyl alcohol

β-D-glucose pentaacetate

Downstream raw materials:

Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[2,5-bis-((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxymethyl)-benzyloxy]-tetrahydro-pyran-4-yl ester

Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-allyloxy-tetrahydro-pyran-4-yl ester

propargyl β-D-glucopyranoside

4-(4-{(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)oxymethyl}-1-H-1,2,3-triazol-1-yl)benzenesulfonamide