3,4,6-Tri-O-acetyl-2-azido-1-O-[tert-butyl(dimethyl)silyl]-2-deoxy-beta-D-glucopyranose

Base Information

• Chemical Name: 3,4,6-Tri-O-acetyl-2-azido-1-O-[tert-butyl(dimethyl)silyl]-2-deoxy-beta-D-glucopyranose
• CAS No.: 99049-65-7
• Molecular Formula: C₁₈H₃₁N₃O₈Si
• Molecular Weight: 445.545
• Hs Code.: 29389090
• DSSTox Substance ID: DTXSID40584091
• Nikkaji Number: J2.177.280A
• Wikidata: Q82475721
• Mol file: 99049-65-7.mol

Synonyms:99049-65-7;3,4,6-Tri-O-acetyl-2-azido-1-O-[tert-butyl(dimethyl)silyl]-2-deoxy-beta-D-glucopyranose;1-O-tert-Butyldimethylsilyl 2-azido-2-deoxy-beta-D-glucopyranoside 3,4,6-triacetate;[(2R,3S,4R,5R,6S)-3,4-diacetyloxy-5-azido-6-[tert-butyl(dimethyl)silyl]oxyoxan-2-yl]methyl acetate;DTXSID40584091;IFAXCGVPFHELQE-HHARLNAUSA-N;1-O-tert-Butyldimethylsilyl 2-azido-2-deoxy- beta -D-glucopyranoside 3,4,6-triacetate;tert-Butyldimethylsilyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-beta-D-glucopyranoside;tert-Butyldimethylsilyl-3,4,6-tri-O-acetyl-2-azido-2-deoxy-ss-D-glucopyranoside

Chemical Property of 3,4,6-Tri-O-acetyl-2-azido-1-O-[tert-butyl(dimethyl)silyl]-2-deoxy-beta-D-glucopyranose

Chemical Property:

• Melting Point: 66-70 °C(lit.)
• PSA: 128.90000
• LogP: 0.57886
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 11
• Exact Mass: 445.18804149
• Heavy Atom Count: 30
• Complexity: 702

Purity/Quality:

98%Min ^*data from raw suppliers

1-O-tert-Butyldimethylsilyl-2-azido-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)OCC1C(C(C(C(O1)O[Si](C)(C)C(C)(C)C)N=[N+]=[N-])OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[Si](C)(C)C(C)(C)C)N=[N+]=[N-])OC(=O)C)OC(=O)C

Technology Process of 3,4,6-Tri-O-acetyl-2-azido-1-O-[tert-butyl(dimethyl)silyl]-2-deoxy-beta-D-glucopyranose

There total 7 articles about 3,4,6-Tri-O-acetyl-2-azido-1-O-[tert-butyl(dimethyl)silyl]-2-deoxy-beta-D-glucopyranose 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: 12.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-arabino-hexopyranose → tert-Butyldimethylsilyl-3,4,6-tri-O-acetyl-2-azido-2-desoxy-β-D-glucopyranosid (99049-65-7) + tert-Butyldimethylsilyl-3,4,6-tri-O-acetyl-2-azido-2-desoxy-α-D-mannopyranosid (99049-66-8)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 6h; Ambient temperature;

Reference yield:

1H-imidazole (288-32-4) + 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose (171032-74-9) + tert-butyldimethylsilyl chloride (18162-48-6) → tert-Butyldimethylsilyl-3,4,6-tri-O-acetyl-2-azido-2-desoxy-β-D-glucopyranosid (99049-65-7)

Guidance literature:

With nitrogen; ammonia; In tetrahydrofuran; methanol; dichloromethane;

Reference yield:

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose (171032-74-9) → tert-Butyldimethylsilyl-3,4,6-tri-O-acetyl-2-azido-2-desoxy-β-D-glucopyranosid (99049-65-7)

Guidance literature:

Multi-step reaction with 2 steps

1: NH₃ / tetrahydrofuran; methanol / 0.25 h

2: 29.8 g / imidazole / CH₂Cl₂ / 2 h

With 1H-imidazole; ammonia; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1002/chem.200390009

upstream raw materials:

tert-butyldimethylsilyl chloride

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose

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

D-glucal triacetate

Downstream raw materials:

O-<2-Azido-3-O-(2-azido-3,4,6-tri-O-benzyl-2-desoxy-β-D-glucopyranosyl)-2-desoxy-4,6-O-isopropyliden-α-D-glucopyranosyl>-trichloracetimidat

tert-Butyldimethylsilyl-2-azido-3-O-<2-azido-3-O-(2-azido-3,4,6-tri-O-benzyl-2-desoxy-β-D-glucopyranosyl)-4,6-O-isopropyliden-2-desoxy-β-D-glucopyranosyl>-4,6-O-isopropyliden-2-desoxy-β-D-glucopyranosid

tert-Butyldimethylsilyl-2-azido-3-O-(2-azido-3,4,6-tri-O-benzyl-2-desoxy-β-D-glucopyranosyl)-4,6-O-isopropyliden-2-desoxy-β-D-glucopyranosid

6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-2-O-levulinoyl-β-D-glucopyranosyl-(1->4)-(3,6-di-O-acetyl-2-azido-2-deoxy-α/β-D-glucopyranosyl trichloroacetimidate