4-O-(4-O-acetyl-3,6-di-O-allyl-2-O-benzyl-β-D-mannopyranosyl)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose

Base Information

• Chemical Name: 4-O-(4-O-acetyl-3,6-di-O-allyl-2-O-benzyl-β-D-mannopyranosyl)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose
• CAS No.: 102728-53-0
• Molecular Formula: C₃₄H₄₁N₃O₁₀
• Molecular Weight: 651.714
• Mol file: 102728-53-0.mol

Synonyms:4-O-(4-O-acetyl-3,6-di-O-allyl-2-O-benzyl-β-D-mannopyranosyl)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose

Chemical Property of 4-O-(4-O-acetyl-3,6-di-O-allyl-2-O-benzyl-β-D-mannopyranosyl)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-O-(4-O-acetyl-3,6-di-O-allyl-2-O-benzyl-β-D-mannopyranosyl)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose

There total 5 articles about 4-O-(4-O-acetyl-3,6-di-O-allyl-2-O-benzyl-β-D-mannopyranosyl)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-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: 65.0%

1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose (55682-57-0) + 4-O-acetyl-3,6-di-O-allyl-2-O-benzyl-α-D-mannopyranosyl bromide (102728-52-9) → 4-O-(4-O-acetyl-3,6-di-O-allyl-2-O-benzyl-β-D-mannopyranosyl)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose (102728-53-0) + Acetic acid (2R,3R,4S,5S,6R)-4-allyloxy-2-allyloxymethyl-6-((1R,2S,3R,4R,5R)-4-azido-3-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-5-benzyloxy-tetrahydro-pyran-3-yl ester

Guidance literature:

With 4 A molecular sieve; silver silicate; In dichloromethane; for 7h; Yields of byproduct given; Ambient temperature;

DOI:10.1016/0008-6215(85)85006-0

Reference yield:

methyl 3,6-di-O-allyl-α-D-mannopyranoside (67381-26-4) → 4-O-(4-O-acetyl-3,6-di-O-allyl-2-O-benzyl-β-D-mannopyranosyl)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose (102728-53-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 48 percent / NaOH, tetrabutylammonium bromide / CH₂Cl₂ / 96 h / Ambient temperature

2: pyridine / 12 h / Ambient temperature

3: H₂SO₄, sodium acetate / acetic acid / 0.58 h / 0 °C

4: HBr / CH₂Cl₂ / 0.17 h / Ambient temperature

5: 65 percent / molecular sieve 4A / silver silicate / CH₂Cl₂ / 7 h / Ambient temperature

With sodium hydroxide; 4 A molecular sieve; sulfuric acid; tetrabutylammomium bromide; hydrogen bromide; sodium acetate; silver silicate; In pyridine; dichloromethane; acetic acid;

DOI:10.1016/0008-6215(85)85006-0

Reference yield:

benzyl bromide (100-39-0) → 4-O-(4-O-acetyl-3,6-di-O-allyl-2-O-benzyl-β-D-mannopyranosyl)-1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose (102728-53-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 48 percent / NaOH, tetrabutylammonium bromide / CH₂Cl₂ / 96 h / Ambient temperature

2: pyridine / 12 h / Ambient temperature

3: H₂SO₄, sodium acetate / acetic acid / 0.58 h / 0 °C

4: HBr / CH₂Cl₂ / 0.17 h / Ambient temperature

5: 65 percent / molecular sieve 4A / silver silicate / CH₂Cl₂ / 7 h / Ambient temperature

With sodium hydroxide; 4 A molecular sieve; sulfuric acid; tetrabutylammomium bromide; hydrogen bromide; sodium acetate; silver silicate; In pyridine; dichloromethane; acetic acid;

DOI:10.1016/0008-6215(85)85006-0

upstream raw materials:

1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose

4-O-acetyl-3,6-di-O-allyl-2-O-benzyl-α-D-mannopyranosyl bromide

methyl 3,6-di-O-allyl-α-D-mannopyranoside

benzyl bromide