2-Acetamido-3,4,6-tri-O-benzyl-2-deoxy-beta-D-glucopyranosyl Azide

Base Information

• Chemical Name: 2-Acetamido-3,4,6-tri-O-benzyl-2-deoxy-beta-D-glucopyranosyl Azide
• CAS No.: 214467-60-4
• Molecular Formula: C29H32 N4 O5
• Molecular Weight: 516.597
• Hs Code.: 29329990
• DSSTox Substance ID: DTXSID30572189
• Nikkaji Number: J1.136.232J
• Wikidata: Q82460473
• Mol file: 214467-60-4.mol

Synonyms:214467-60-4;2-Acetamido-3,4,6-tri-O-benzyl-2-deoxy-beta-D-glucopyranosyl Azide;N-[(2R,3R,4R,5S,6R)-2-azido-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]acetamide;SCHEMBL23161900;DTXSID30572189;XOOBJDMHDWWHLZ-HWVUQVAQSA-N;MFCD06797049;T70564;J-014076;2-Acetamido-3,4,6-tri-O-benzyl-2-deoxy-b-D-glucopyranosyl azide;2-Acetamido-3,4,6-tri-O-benzyl-2-deoxy- beta -D-glucopyranosyl azide;2-Acetamido-3,4,6-tri-O-benzyl-2-deoxy-beta-D-glucopyranosyl azide, >=98.0% (HPLC)

Chemical Property of 2-Acetamido-3,4,6-tri-O-benzyl-2-deoxy-beta-D-glucopyranosyl Azide

Chemical Property:

• Melting Point: 105 °C
• Refractive Index: 6 ° (C=1, CHCl3)
• PSA: 115.77000
• LogP: 4.75756
• Storage Temp.: Freezer
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 12
• Exact Mass: 516.23727013
• Heavy Atom Count: 38
• Complexity: 745

Purity/Quality:

98%,99%, ^*data from raw suppliers

2-Acetamido-3,4,6-tri-O-benzyl-2-deoxy-b-D-glucopyranosyl azide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)NC1C(C(C(OC1N=[N+]=[N-])COCC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1N=[N+]=[N-])COCC2=CC=CC=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4
• Uses: 2-Acetamido-3,4,6-tri-O-benzyl-2-deoxy-beta-D-glucopyranosyl Azide (CAS# 214467-60-4) is a glycosyl azide used in the preparation of nonglycosylated androgenic gland hormone (AGH) and glycosylated AGH with N-linked glycan using expressed protein ligation.

Technology Process of 2-Acetamido-3,4,6-tri-O-benzyl-2-deoxy-beta-D-glucopyranosyl Azide

There total 7 articles about 2-Acetamido-3,4,6-tri-O-benzyl-2-deoxy-beta-D-glucopyranosyl Azide 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: 71.0%

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) + N-Trimethylsilylacetamide (13435-12-6) → azido 3,4,6-tri-O-benzyl-2-N-acetylamino-2-deoxy-β-D-glucopyranoside (214467-60-4) + azido 3,4,6-tri-O-benzyl-2-N-acetylamino-2-deoxy-α-D-mannopyranoside

Guidance literature:

3,4,6-tri-O-benzyl-D-glucal; With thianthrene-5-oxide; trifluoromethanesulfonic acid anhydride; In dichloromethane; chloroform; at -78 ℃; for 0.2h;

N-Trimethylsilylacetamide; With N,N-diethylaniline; In dichloromethane; chloroform; at 23 ℃; for 1h;

With sodium azide; copper(II) bis(trifluoromethanesulfonate); In N,N-dimethyl-formamide; for 48h; Further stages.;

DOI:10.1021/ja026281n

Reference yield: 52.0%

2-N-acetylamido-2-deoxy-β-D-glucopyranosyl azide (29847-23-2) + benzyl bromide (100-39-0) → azido 3,4,6-tri-O-benzyl-2-N-acetylamino-2-deoxy-β-D-glucopyranoside (214467-60-4)

Guidance literature:

2-N-acetylamido-2-deoxy-β-D-glucopyranosyl azide; benzyl bromide; With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃;

With barium dihydroxide; barium(II) oxide; In dichloromethane; N,N-dimethyl-formamide; Heating;

DOI:10.1081/CAR-120016847

Reference yield:

acetic anhydride (108-24-7) + (2R,3R,4R,5S,6R)-2-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-ylamine → azido 3,4,6-tri-O-benzyl-2-N-acetylamino-2-deoxy-β-D-glucopyranoside (214467-60-4)

Guidance literature:

With pyridine; at 20 ℃;

DOI:10.1021/jm801577r

upstream raw materials:

3,4,6-tri-O-benzyl-D-glucal

N-Trimethylsilylacetamide

2-N-acetylamido-2-deoxy-β-D-glucopyranosyl azide

benzyl bromide

Downstream raw materials:

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

N-{2-acetamido-4-O-[3-[[(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)amino]carbonyl]propanoyl]-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl}-3-(benzyloxycarbonylamino)propanoic acid amide

2-acetamido-4-O-[3-[[(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)amino]carbonyl]propanoyl]-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl azide

2-acetamido-4-O-[3-[[(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)amino]carbonyl]propanoyl]-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosylamine

Refernces

• 1、 Liu, Jing,Gin, David Y.. "C2-amidoglycosylation. Scope and mechanism of nitrogen transfer". . p. 9789 - 9797. Retrieved 2007/10/03.
• 2、 Kerekgyarto, Janos,Agoston, Karoly,Batta, Gyula,Kamerling, Johannis P.,Vliegenthart, Johannes F. G.. "Synthesis of fully and partially benzylated glycosyl azides via thioalkyl glycosides as precursors for the preparation of N-glycopeptides". . p. 7189 - 7192. Retrieved 2007/10/03.