Benzyl 4,6-O-benzylidene-2-deoxy-2-[(1-hydroxyethylidene)amino]hexopyranoside

Base Information

• Chemical Name: Benzyl 4,6-O-benzylidene-2-deoxy-2-[(1-hydroxyethylidene)amino]hexopyranoside
• CAS No.: 13343-63-0
• Molecular Formula: C22H25 N O6
• Molecular Weight: 399.444
• Hs Code.: 29329990
• DSSTox Substance ID: DTXSID40928118
• Wikidata: Q82902851
• Mol file: 13343-63-0.mol

Synonyms:DTXSID40928118;AKOS015895909;Benzyl 4,6-O-benzylidene-2-deoxy-2-[(1-hydroxyethylidene)amino]hexopyranoside

Chemical Property of Benzyl 4,6-O-benzylidene-2-deoxy-2-[(1-hydroxyethylidene)amino]hexopyranoside

Chemical Property:

• Appearance/Colour: White Solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 256-261 °C (dec.)
• Boiling Point: 650.552oC at 760 mmHg
• PKA: 12.71±0.70(Predicted)
• Flash Point: 347.242oC
• PSA: 86.25000
• Density: 1.306g/cm3
• LogP: 2.29880
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 399.16818752
• Heavy Atom Count: 29
• Complexity: 533

Purity/Quality:

99% ^*data from raw suppliers

Benzyl 2-Acetamido-4,6-O-benzylidene-2-deoxy-a-D-glucopyranoside| ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)NC1C(C2C(COC(O2)C3=CC=CC=C3)OC1OCC4=CC=CC=C4)O
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H]([C@H]2[C@@H](CO[C@@H](O2)C3=CC=CC=C3)O[C@@H]1OCC4=CC=CC=C4)O
• Uses: Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside is a useful synthetic intermediate for carbohydrate and oligosaccharide synthesis.

Technology Process of Benzyl 4,6-O-benzylidene-2-deoxy-2-[(1-hydroxyethylidene)amino]hexopyranoside

There total 39 articles about Benzyl 4,6-O-benzylidene-2-deoxy-2-[(1-hydroxyethylidene)amino]hexopyranoside 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%

benzaldehyde dimethyl acetal (1125-88-8) + benzyl 2-acetamido-2-deoxy-α-D-glucopyranoside (13343-62-9,347411-88-5) → benzyl 4,6-O-benzylidene-2-acetylamino-2-deoxy-α-D-glucopyranoside (13343-63-0)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

DOI:10.1080/07328303.2013.815196

Reference yield: 88.2%

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) + benzaldehyde (100-52-7) → benzyl 4,6-O-benzylidene-2-acetylamino-2-deoxy-α-D-glucopyranoside (13343-63-0)

Guidance literature:

With zinc(II) chloride; at 20 - 25 ℃;

Reference yield: 87.0%

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) + benzaldehyde (100-52-7) → 1-O-benzyl-N-acetyl-4,6-O-benzylidene-D-glucosamine (101223-84-1,3554-91-4,13343-61-8,13343-63-0,19374-64-2,27539-62-4,38191-73-0,78246-81-8,78247-23-1,81655-20-1,117182-56-6,134308-75-1)

Guidance literature:

With toluene-4-sulfonic acid; orthoformic acid triethyl ester; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1691/ph.2008.7675

upstream raw materials:

phenylmethyl 2-acetylamino-2-deoxy-α-D-mannopyranoside

benzaldehyde dimethyl acetal

benzyl 4,6-O-benzylidene-2-amino-2-deoxy-α-D-glucopyranoside

acetic anhydride

Downstream raw materials:

N-acetyl-1-O-benzyl-4,6-O-benzylidenemuramic acid

benzyl 4,6-O-benzylidene-2-amino-2-deoxy-α-D-glucopyranoside

benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-methyl-α-D-glucopyranoside

benzyl 2-acetamido-3-O-(2,3,4-tri-O-acetyl-β-D-xylopyranosyl)-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

Refernces

• 1、 Wasonga, Gilbert,Tatara, Yota,Kakizaki, Ikuko,Huang, Xuefei. "Synthesis of N -acetyl glucosamine analogs as inhibitors for hyaluronan biosynthesis". . p. 392 - 409. Retrieved 2013/10/08.
• 2、 -. "Phosphoramidates of monosaccharides". Page/Page column 29. . Retrieved 2012/07/14.