O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α,β-D-glucopyranosyl) trichloroacetimidate

Base Information

• Chemical Name: O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α,β-D-glucopyranosyl) trichloroacetimidate
• CAS No.: 135415-92-8
• Molecular Formula: C₂₄H₂₅Cl₃N₄O₆
• Molecular Weight: 571.845
• Mol file: 135415-92-8.mol

Synonyms:O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α,β-D-glucopyranosyl) trichloroacetimidate

Chemical Property of O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α,β-D-glucopyranosyl) trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α,β-D-glucopyranosyl) trichloroacetimidate

There total 11 articles about O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α,β-D-glucopyranosyl) trichloroacetimidate 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: 98.0%

trichloroacetonitrile (545-06-2) + 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α/β-D-glucopyranose → O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α,β-D-glucopyranosyl) trichloroacetimidate (135415-92-8)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.3987/COM-11-S(P)69

Reference yield:

1,6-anhydro-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose (55682-48-9) → O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α,β-D-glucopyranosyl) trichloroacetimidate (135415-92-8)

Guidance literature:

Multi-step reaction with 3 steps

1: t-butyldimethylsiyl triflate / 0.33 h / 0 °C

2: ammonia / methanol; tetrahydrofuran / 0 °C

3: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 3 h / 20 °C

With t-butyldimethylsiyl triflate; ammonia; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1002/cmdc.201400019

Reference yield:

3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-glucopyranose → O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α,β-D-glucopyranosyl) trichloroacetimidate (135415-92-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 29.8 g / imidazole / CH₂Cl₂ / 2 h

2: NaOMe; MeOH / 0.25 h

3: 933 mg / 2,4,6-collidine / 5 h / -40 - 20 °C

4: 80 percent / molecular sieves 4 Angstroem; Ag₂O / CH₂Cl₂ / 48 h

5: glacial AcOH; TBAF / tetrahydrofuran / 0.5 h

6: 708 mg / DBU / CH₂Cl₂ / 0.75 h

With 1H-imidazole; 2,4,6-trimethyl-pyridine; methanol; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium methylate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; silver(l) oxide; In tetrahydrofuran; dichloromethane;

DOI:10.1002/chem.200390009

upstream raw materials:

trichloroacetonitrile

tert-Butyldimethylsilyl-2-azido-2-desoxy-β-D-glucopyranosid

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

tert-Butyldimethylsilyl-3,4,6-tri-O-acetyl-2-azido-2-desoxy-β-D-glucopyranosid

Downstream raw materials:

6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-1,2-O-isopropylidene-α-D-glucopyranosyluronate

6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1->4)-methyl 3-O-benzyl-1,2-O-cyclopentylidene-α-D-glucopyranosyluronate

methyl [dimethylthexylsilyl 4-O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-β-L-idopyranoside]uronate

n-penten-4-yl-6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside