3,4,6-Tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl bromide

Base Information

• Chemical Name: 3,4,6-Tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl bromide
• CAS No.: 67124-60-1
• Molecular Formula: C₁₅H₁₉BrCl₃NO₉
• Molecular Weight: 543.58
• Mol file: 67124-60-1.mol

Synonyms:3,4,6-Tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl bromide

Chemical Property of 3,4,6-Tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl bromide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4,6-Tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl bromide

There total 1 articles about 3,4,6-Tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl bromide 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: 3.0%

benzyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside (133940-44-0,133940-45-1) → 3,4,6-Tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl bromide (67124-60-1) + benzyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside (133940-44-0)

Guidance literature:

With trimethylsilyl bromide; zinc dibromide; In dichloromethane; for 5h; Yields of byproduct given. Title compound not separated from byproducts; Ambient temperature;

DOI:10.1248/cpb.39.2502

Reference yield: 90.0%

3,4,6-Tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl bromide (67124-60-1) + Boc-Hcy-Ala-OBn (613244-82-9) → N-tert-butoxycarbonyl-S-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-L-homocysteinyl-L-alanine benzyl ester (613244-60-3)

Guidance literature:

With tetra(n-butyl)ammonium hydrogensulfate; sodium carbonate; In ethyl acetate; at 20 ℃; for 8h;

DOI:10.1055/s-2003-39405

Reference yield: 90.0%

3,4,6-Tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl bromide (67124-60-1) + 1,6-anhydro-2-azido-4-O-benzyl-2-deoxy-β-D-glucopyranose (55682-47-8) → 1,6-anhydro-2-azido-4-O-benzyl-3-O-(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl)-2-deoxy-β-D-glucopyranose (848850-43-1)

Guidance literature:

With silver trifluoromethanesulfonate; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/j.tetasy.2004.11.053

upstream raw materials:

benzyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

Downstream raw materials:

allyl O-<3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl>-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside

allyl 2-acetamido-6-O-<3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl>-3-O-benzoyl-4-O-benzyl-2-deoxy-β-D-glucopyranoside

Allyl-O-<3,4,6-tri-O-acetyl-2-desoxy-2-(2,2,2-trichlorethoxycarbonylamino)-β-D-glucopyranosyl)-(1->2)-O-<<3,4,6-tri-O-acetyl-2-desoxy-2-(2,2,2-trichlorethoxycarbonylamino)-β-D-glucopyranosyl>-(1->4)>-3,6-di-O-benzyl-α-D-mannopyranosid

Benzyl-6-O-<3,4,6-tri-O-acetyl-2-desoxy-2-(2,2,2-trichlorethoxycarbonylamino)-β-D-glucopyranosyl>-3-O-benzyl-2-<(R)-3-benzyloxytetradecanoylamino>-2-desoxy-α-D-glucopyranosid