Benzyl2-acetamido-2-deoxy-3,4,6-tri-o-acetyl-beta-D-glucopyranoside

Base Information

• Chemical Name: Benzyl2-acetamido-2-deoxy-3,4,6-tri-o-acetyl-beta-D-glucopyranoside
• CAS No.: 13343-66-3
• Molecular Formula: C₂₁H₂₇NO₉
• Molecular Weight: 437.447
• Hs Code.: 2938909090
• DSSTox Substance ID: DTXSID60451099
• Nikkaji Number: J702.817B
• Mol file: 13343-66-3.mol

Synonyms:13343-66-3;Benzyl2-acetamido-2-deoxy-3,4,6-tri-o-acetyl-beta-D-glucopyranoside;BENZYL 2-ACETAMIDO-2-DEOXY-3,4,6-TRI-O-ACETYL-BETA-D-GLUCOPYRANOSIDE;[(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-phenylmethoxyoxan-2-yl]methyl acetate;Benzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-glucopyranoside;(2R,3S,4R,5R,6R)-5-Acetamido-2-(acetoxymethyl)-6-(benzyloxy)tetrahydro-2H-pyran-3,4-diyl diacetate;SCHEMBL8931470;DTXSID60451099;IDEBBPWXWFHKBU-PFAUGDHASA-N;AKOS022180727;CS-T-48774;W-201100;1-O-Benzyl-N,3-O,4-O,6-O-tetraacetyl-beta-D-glucosamine;Benzyl 2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl-?-D-glucopyranoside;Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-a-D-glucopyranoside;b-D-Glucopyranoside,phenylmethyl2-(acetylamino)-2-deoxy-,3,4,6-triacetate;Benzyl 2-acetamido-2-deoxy-3,4,6-tri-o-acetyl-beta-D-glucopyranosid;Benzyl 2-acetamido-2-deoxy-3,4,6-tri-o-acetyl-betA1-D-glucopyranoside;Benzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranoside

Chemical Property of Benzyl2-acetamido-2-deoxy-3,4,6-tri-o-acetyl-beta-D-glucopyranoside

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.532
• Boiling Point: 586.955 °C at 760 mmHg
• Flash Point: 308.779 °C
• PSA: 126.46000
• Density: 1.267 g/cm³
• LogP: 1.25020
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 11
• Exact Mass: 437.16858144
• Heavy Atom Count: 31
• Complexity: 647

Purity/Quality:

98%min ^*data from raw suppliers

Benzyl2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-b-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC1C(C(C(OC1OCC2=CC=CC=C2)COC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1OCC2=CC=CC=C2)COC(=O)C)OC(=O)C)OC(=O)C

Technology Process of Benzyl2-acetamido-2-deoxy-3,4,6-tri-o-acetyl-beta-D-glucopyranoside

There total 57 articles about Benzyl2-acetamido-2-deoxy-3,4,6-tri-o-acetyl-beta-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: 95.0%

2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl acetate (3006-60-8,4539-83-7,6730-10-5,7772-79-4,7784-54-5,10385-50-9,26151-16-6,76375-60-5,76375-61-6,95341-98-3,95341-99-4,134451-91-5,134451-96-0,136982-81-5,145375-11-7,148347-15-3,14086-90-9) + benzyl alcohol (100-51-6,185532-71-2) → benzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside (10375-65-2,13318-46-2,13343-66-3,19374-72-2,33423-34-6,34029-78-2,41355-94-6,110911-57-4,141019-71-8)

Guidance literature:

With ytterbium(III) triflate; In dichloromethane; at 60 ℃; stereoselective reaction;

DOI:10.1021/acs.joc.6b02929

Reference yield: 93.0%

benzyl alcohol (100-51-6,185532-71-2) + 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose (3006-60-8,4539-83-7,6730-10-5,7772-79-4,7784-54-5,10385-50-9,14086-90-9,26151-16-6,76375-60-5,76375-61-6,95341-98-3,95341-99-4,134451-91-5,134451-96-0,136982-81-5,145375-11-7,148347-15-3) → benzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside (10375-65-2,13318-46-2,13343-66-3,19374-72-2,33423-34-6,34029-78-2,41355-94-6,110911-57-4,141019-71-8)

Guidance literature:

With iron(III) trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1039/c7ob01201b

Reference yield: 90.0%

acetic anhydride (108-24-7) + benzyl 2-acetamido-2-deoxy-β-D-glucopyranoside (3055-51-4,3554-93-6,10380-86-6,13343-62-9,13343-67-4,19374-70-0,33423-30-2,33501-36-9,41355-95-7,86834-14-2,111003-11-3,347411-88-5) → benzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside (10375-65-2,13318-46-2,13343-66-3,19374-72-2,33423-34-6,34029-78-2,41355-94-6,110911-57-4,141019-71-8)

Guidance literature:

With ammonium cerium (IV) nitrate; at 50 ℃; for 1h;

DOI:10.1080/00397911.2016.1230219

upstream raw materials:

acetic anhydride

benzyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-β-D-glucopyranoside

benzyl alcohol

2-acetylamino-3,4,6-triacetyl-2-deoxy-α-D-glucopyranosyl bromide

Downstream raw materials:

3,4,6-tri-O-acetyl-2-acetamido-1-O-[bis(benzyloxy)phophoryl]-2-deoxy-α-D-glucopyranose

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphanyloxy)-tetrahydro-pyran-4-yl ester

benzyl 3,4,6-tri-O-acetyl-2-acetylamino-2-deoxy-α-D-glucopyranoside

2-deoxy-2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranose

Refernces

• 1、 DiFrancesco, Benjamin R.,Morrison, Zachary A.,Nitz, Mark. "Monosaccharide inhibitors targeting carbohydrate esterase family 4 de-N-acetylases". . p. 5631 - 5643. Retrieved 2018/10/24.
• 2、 Schultz, Victor L.,Zhang, Xing,Linkens, Kathryn,Rimel, Jenna,Green, Dixy E.,Deangelis, Paul L.,Linhardt, Robert J.. "Chemoenzymatic Synthesis of 4-Fluoro-N-Acetylhexosamine Uridine Diphosphate Donors: Chain Terminators in Glycosaminoglycan Synthesis". . p. 2243 - 2248. Retrieved 2017/02/26.