methyl 3,4,6-tri-O-benzyl-2-bromo-2-deoxy-α-D-mannopyranoside

Base Information

• Chemical Name: methyl 3,4,6-tri-O-benzyl-2-bromo-2-deoxy-α-D-mannopyranoside
• CAS No.: 77770-58-2
• Molecular Formula: C₂₈H₃₁BrO₅
• Molecular Weight: 527.455
• Mol file: 77770-58-2.mol

Synonyms:methyl 3,4,6-tri-O-benzyl-2-bromo-2-deoxy-α-D-mannopyranoside

Chemical Property of methyl 3,4,6-tri-O-benzyl-2-bromo-2-deoxy-α-D-mannopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3,4,6-tri-O-benzyl-2-bromo-2-deoxy-α-D-mannopyranoside

There total 4 articles about methyl 3,4,6-tri-O-benzyl-2-bromo-2-deoxy-α-D-mannopyranoside 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: 89.0%

(2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-ol (20672-67-7,40246-25-1,40246-30-8,73415-91-5,73445-27-9,81086-90-0,148888-64-6) → methyl 3,4,6-tri-O-benzyl-2-bromo-2-deoxy-α-D-mannopyranoside (77770-58-2)

Guidance literature:

With 1H-imidazole; triphenylphosphine; 2,3,5-tribromoimidazole; In toluene; Heating; 120 deg C, 6 h;

Reference yield: 70.0%

methyl 3,4,6-tri-O-acetyl-2-bromo-2-deoxy-α-D-mannopyranoside (63069-63-6) + 2,4,6-tris(benzyloxy)-1,3,5-triazine (7285-83-8) → methyl 3,4,6-tri-O-benzyl-2-bromo-2-deoxy-α-D-mannopyranoside (77770-58-2)

Guidance literature:

methyl 3,4,6-tri-O-acetyl-2-bromo-2-deoxy-α-D-mannopyranoside; In methanol; at 20 ℃; for 8h;

2,4,6-tris(benzyloxy)-1,3,5-triazine; In 1,4-dioxane; at 20 ℃; for 0.5h; Molecular sieve;

With trifluorormethanesulfonic acid; In 1,4-dioxane; at 0 - 20 ℃; for 1h; Molecular sieve;

DOI:10.1002/anie.202006115

Reference yield:

methanol (67-56-1) + 3,4,6-tri-O-benzyl-D-glucal (55628-54-1) → methyl 3,4,6-tri-O-benzyl-2-bromo-2-deoxy-α-D-mannopyranoside (77770-58-2) + (2R,3R,4S,5R,6R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-bromo-6-methoxy-tetrahydro-pyran (188439-90-9)

Guidance literature:

With bromine; Product distribution; other reagent;

DOI:10.1016/S0040-4020(97)00064-1

upstream raw materials:

(2S,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-ol

methanol

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

methyl 3,4,6-tri-O-acetyl-2-bromo-2-deoxy-α-D-mannopyranoside