[benzyl (2,3,4-tri-O-benzyl-β-D-glucopyranosyl)uronate]-(1→ 2)-1,6-anhydro-4-O-benzyl-3-O-(2-naphthalenylmethyl)-β-D-mannopyranose

Base Information

• Chemical Name: [benzyl (2,3,4-tri-O-benzyl-β-D-glucopyranosyl)uronate]-(1→ 2)-1,6-anhydro-4-O-benzyl-3-O-(2-naphthalenylmethyl)-β-D-mannopyranose
• CAS No.: 1607444-93-8
• Molecular Formula: C₅₈H₅₆O₁₁
• Molecular Weight: 929.076
• Mol file: 1607444-93-8.mol

Synonyms:[benzyl (2,3,4-tri-O-benzyl-β-D-glucopyranosyl)uronate]-(1→ 2)-1,6-anhydro-4-O-benzyl-3-O-(2-naphthalenylmethyl)-β-D-mannopyranose

Chemical Property of [benzyl (2,3,4-tri-O-benzyl-β-D-glucopyranosyl)uronate]-(1→ 2)-1,6-anhydro-4-O-benzyl-3-O-(2-naphthalenylmethyl)-β-D-mannopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [benzyl (2,3,4-tri-O-benzyl-β-D-glucopyranosyl)uronate]-(1→ 2)-1,6-anhydro-4-O-benzyl-3-O-(2-naphthalenylmethyl)-β-D-mannopyranose

There total 5 articles about [benzyl (2,3,4-tri-O-benzyl-β-D-glucopyranosyl)uronate]-(1→ 2)-1,6-anhydro-4-O-benzyl-3-O-(2-naphthalenylmethyl)-β-D-mannopyranose 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: 34.0%

C30H32O11 + benzyl bromide (100-39-0) → [benzyl (2,3,4-tri-O-benzyl-β-D-glucopyranosyl)uronate]-(1→ 2)-1,6-anhydro-4-O-benzyl-3-O-(2-naphthalenylmethyl)-β-D-mannopyranose (1607444-93-8)

Guidance literature:

With sodium hydride; In dimethyl sulfoxide; at 15 - 20 ℃; for 0.666667h;

DOI:10.1016/j.carres.2014.01.022

Reference yield:

benzyl 2,3,4-tri-O-benzyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate (184698-69-9,159420-94-7) + 1,6-anhydro-4-O-benzyl-3-O-(2-naphthalenylmethyl)-β-D-mannopyranose → [benzyl (2,3,4-tri-O-benzyl-β-D-glucopyranosyl)uronate]-(1→ 2)-1,6-anhydro-4-O-benzyl-3-O-(2-naphthalenylmethyl)-β-D-mannopyranose (1607444-93-8) + [benzyl (2,3,4-tri-O-benzyl-α-D-glucopyranosyl)uronate]-(1→ 2)-1,6-anhydro-4-O-benzyl-3-O-(2-naphthalenylmethyl)-β-D-mannopyranose (1607444-94-9)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; Solvent; Temperature; Molecular sieve; Inert atmosphere;

DOI:10.1016/j.carres.2014.01.022

Reference yield:

1,6-anhydro-4-O-benzyl-3-O-(2-naphthalenylmethyl)-β-D-mannopyranose → [benzyl (2,3,4-tri-O-benzyl-β-D-glucopyranosyl)uronate]-(1→ 2)-1,6-anhydro-4-O-benzyl-3-O-(2-naphthalenylmethyl)-β-D-mannopyranose (1607444-93-8)

Guidance literature:

Multi-step reaction with 3 steps

1: t-butyldimethylsiyl triflate / dichloromethane / 1 h / 0 °C / Molecular sieve

2: sodium methylate; methanol / 1 h / 20 °C

3: sodium hydride / dimethyl sulfoxide / 0.67 h / 15 - 20 °C

With methanol; t-butyldimethylsiyl triflate; sodium methylate; sodium hydride; In dichloromethane; dimethyl sulfoxide;

DOI:10.1016/j.carres.2014.01.022

upstream raw materials:

benzyl bromide

benzyl 2,3,4-tri-O-benzyl-1-O-(trichloroacetimidoyl)-α-D-glucopyranuronate

methyl (2,3,4-tri-O-acetyl-β-D-glucopyranosyl)uronate-(1→2)-1,6-anhydro-4-O-benzyl-3-O-(2-naphthalenylmethyl)-β-D-mannopyranose