Benzyl 2-Acetamido-2-deoxy-beta-D-glucopyranoside

Base Information

• Chemical Name: Benzyl 2-Acetamido-2-deoxy-beta-D-glucopyranoside
• CAS No.: 13343-67-4
• Molecular Formula: C₁₅H₂₁NO₆
• Molecular Weight: 311.335
• Hs Code.: 29389090
• DSSTox Substance ID: DTXSID201236521
• Nikkaji Number: J1.238.489K
• ChEMBL ID: CHEMBL1818656
• Mol file: 13343-67-4.mol

Synonyms:13343-67-4;Benzyl 2-Acetamido-2-deoxy-beta-D-glucopyranoside;Benzyl 2-acetamido-2-deoxy-b-D-glucopyranoside;CHEMBL1818656;N-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-phenylmethoxyoxan-3-yl]acetamide;N-((2R,3R,4R,5S,6R)-2-(Benzyloxy)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)acetamide;SCHEMBL542635;N-Acetylglucosamine-beta-benzyl;DTXSID201236521;BDBM50466400;MFCD00070372;AKOS015910500;Benzyl 2-Acetamido-2-deoxy-?-D-glucopyranoside;Benzyl 2-Acetamido-2-deoxy- beta -D-glucopyranoside;b-D-Glucopyranoside,phenylmethyl2-(acetylamino)-2-deoxy-;Phenylmethyl 2-(acetylamino)-2-deoxy-beta-D-glucopyranoside;N-[(2R,3R,4R,5S,6R)-2-(BENZYLOXY)-4,5-DIHYDROXY-6-(HYDROXYMETHYL)OXAN-3-YL]ACETAMIDE

Chemical Property of Benzyl 2-Acetamido-2-deoxy-beta-D-glucopyranoside

Chemical Property:

• Appearance/Colour: White solid
• Melting Point: 183-198 °C
• Refractive Index: 1.59
• Boiling Point: 594.855 °C at 760 mmHg
• Flash Point: 313.557 °C
• PSA: 108.25000
• LogP: -0.46220
• Storage Temp.: −20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly, Heated)
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 311.13688739
• Heavy Atom Count: 22
• Complexity: 360

Purity/Quality:

98%Min ^*data from raw suppliers

Benzyl2-Acetamido-2-deoxy-β-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)CO)O)O
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1OCC2=CC=CC=C2)CO)O)O

Technology Process of Benzyl 2-Acetamido-2-deoxy-beta-D-glucopyranoside

There total 39 articles about Benzyl 2-Acetamido-2-deoxy-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: 100.0%

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) → 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)

Guidance literature:

With methanol; sodium methylate; at 20 ℃;

DOI:10.1021/ja020627c

Reference yield: 81.6%

N-Acetyl-D-glucosamine (7512-17-6,72-87-7,1136-42-1,1136-44-3,6082-29-7,6730-06-9,7772-94-3,10036-64-3,14131-60-3,14131-64-7,14131-68-1,14215-68-0,62057-49-2,62057-50-5,62057-51-6,62057-52-7,62057-53-8,62057-54-9,62057-55-0,62057-56-1,62075-50-7,62137-54-6,134451-97-1,134522-12-6,148347-16-4) + benzyl alcohol (100-51-6,185532-71-2) → benzyl 2-deoxy-2-(N-acetylamino)-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)

Guidance literature:

With acetyl chloride; In methanol; at 20 - 25 ℃; for 24h; Cooling with ice;

Reference yield: 76.0%

N-Acetyl-D-glucosamine (7512-17-6,72-87-7,1136-42-1,1136-44-3,6082-29-7,6730-06-9,7772-94-3,10036-64-3,14131-60-3,14131-64-7,14131-68-1,14215-68-0,62057-49-2,62057-50-5,62057-51-6,62057-52-7,62057-53-8,62057-54-9,62057-55-0,62057-56-1,62075-50-7,62137-54-6,134451-97-1,134522-12-6,148347-16-4) + benzyl alcohol (100-51-6,185532-71-2) → 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-2-deoxy-α-D-glucopyranoside (13343-62-9,347411-88-5)

Guidance literature:

With hydrogenchloride; at 85 ℃; for 2h; Title compound not separated from byproducts;

DOI:10.1002/jlac.198619860104

upstream raw materials:

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

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

N-Acetyl-D-glucosamine

benzyl alcohol

Downstream raw materials:

benzyl 2-acetamido-6-bromo-2,6-dideoxy-α-D-glucopyranoside

benzyl 2-acetamido-3-O-acetyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

Acetic acid (2S,3S,4R,5R,6S)-4,5-diacetoxy-2-((2R,3S,4R,5R,6R)-3-acetylamino-2-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-ylsulfanyl)-6-methyl-tetrahydro-pyran-3-yl ester

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". supporting information. p. 2243 - 2248. Retrieved 2017/02/26.