methyl O-(2-azido-4,6-O-benzylidene-3-O-bromoacetyl-2-deoxy-α-D-glucopyranosyl)-(1<*>3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1<*>3)-2,4-di-O-benzyl-α-L-rhamnopyranoside

Base Information

• Chemical Name: methyl O-(2-azido-4,6-O-benzylidene-3-O-bromoacetyl-2-deoxy-α-D-glucopyranosyl)-(1<*>3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1<*>3)-2,4-di-O-benzyl-α-L-rhamnopyranoside
• CAS No.: 160529-52-2
• Molecular Formula: C₅₆H₆₀BrN₃O₁₅
• Molecular Weight: 1095.01
• Mol file: 160529-52-2.mol

Synonyms:methyl O-(2-azido-4,6-O-benzylidene-3-O-bromoacetyl-2-deoxy-α-D-glucopyranosyl)-(1<*>3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1<*>3)-2,4-di-O-benzyl-α-L-rhamnopyranoside

Chemical Property of methyl O-(2-azido-4,6-O-benzylidene-3-O-bromoacetyl-2-deoxy-α-D-glucopyranosyl)-(1<*>3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1<*>3)-2,4-di-O-benzyl-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl O-(2-azido-4,6-O-benzylidene-3-O-bromoacetyl-2-deoxy-α-D-glucopyranosyl)-(1<*>3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1<*>3)-2,4-di-O-benzyl-α-L-rhamnopyranoside

There total 8 articles about methyl O-(2-azido-4,6-O-benzylidene-3-O-bromoacetyl-2-deoxy-α-D-glucopyranosyl)-(1<*>3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1<*>3)-2,4-di-O-benzyl-α-L-rhamnopyranoside 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: 53.0%

2-azido-4,6-O-benzylidene-3-O-bromoacetyl-2-deoxy-β-D-glucopyranosyl chloride (149827-66-7) + methyl O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1<*>3)-2,4-di-O-benzyl-α-L-rhamnopyranoside (160529-51-1) → methyl O-(2-azido-4,6-O-benzylidene-3-O-bromoacetyl-2-deoxy-α-D-glucopyranosyl)-(1<*>3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1<*>3)-2,4-di-O-benzyl-α-L-rhamnopyranoside (160529-52-2)

Guidance literature:

With 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; for 1h;

DOI:10.1016/0008-6215(94)80035-9

Reference yield:

(2R,3R,4R,5R,6S)-3,5-Bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-ol (69850-47-1) → methyl O-(2-azido-4,6-O-benzylidene-3-O-bromoacetyl-2-deoxy-α-D-glucopyranosyl)-(1<*>3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1<*>3)-2,4-di-O-benzyl-α-L-rhamnopyranoside (160529-52-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 21 percent / MeSiOTf, 4A molecular sieves / CH₂Cl₂ / 5 h / 25 °C

2: 86 percent / HBF₄ / methanol; diethyl ether / 24 h / 25 °C

3: 53 percent / 2,6-di-tert-butyl-4-methylpyridine, 4A molecular sieves, AgOTf / CH₂Cl₂ / 1 h

With tetrafluoroboric acid; 2,6-di-tert-butyl-4-methylpyridine; MeSiOTf; 4 A molecular sieve; silver trifluoromethanesulfonate; In methanol; diethyl ether; dichloromethane;

DOI:10.1016/0008-6215(94)80035-9

Reference yield:

methyl 2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside (90164-72-0) → methyl O-(2-azido-4,6-O-benzylidene-3-O-bromoacetyl-2-deoxy-α-D-glucopyranosyl)-(1<*>3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1<*>3)-2,4-di-O-benzyl-α-L-rhamnopyranoside (160529-52-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 96 percent / pyridine / 2 h / 25 °C

2: 30 percent / conc. H₂SO₄ / 0.5 h

3: 21 percent / MeSiOTf, 4A molecular sieves / CH₂Cl₂ / 5 h / 25 °C

4: 86 percent / HBF₄ / methanol; diethyl ether / 24 h / 25 °C

5: 53 percent / 2,6-di-tert-butyl-4-methylpyridine, 4A molecular sieves, AgOTf / CH₂Cl₂ / 1 h

With pyridine; tetrafluoroboric acid; 2,6-di-tert-butyl-4-methylpyridine; MeSiOTf; 4 A molecular sieve; sulfuric acid; silver trifluoromethanesulfonate; In methanol; diethyl ether; dichloromethane;

DOI:10.1016/0008-6215(94)80035-9

upstream raw materials:

2-azido-4,6-O-benzylidene-3-O-bromoacetyl-2-deoxy-β-D-glucopyranosyl chloride

methyl O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1<*>3)-2,4-di-O-benzyl-α-L-rhamnopyranoside

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

methyl 2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

Downstream raw materials:

methyl O-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl)-(1<*>3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1<*>3)-2,4-di-O-benzyl-α-L-rhamnopyranoside

methyl O-(2-amino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl)-(1<*>3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1<*>3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside

methyl O-(2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl)-(1<*>3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1<*>3)-2,4-di-O-benzyl-α-L-rhamnopyranoside