1-Hydroxy-5,8-dimethoxy-2-(3',4',6'-tri-O-benzyl-2'-deoxy-β-D-arabino-hexopyranosyl)naphthalene

Base Information

• Chemical Name: 1-Hydroxy-5,8-dimethoxy-2-(3',4',6'-tri-O-benzyl-2'-deoxy-β-D-arabino-hexopyranosyl)naphthalene
• CAS No.: 161258-48-6
• Molecular Formula: C₃₉H₄₀O₇
• Molecular Weight: 620.742
• Mol file: 161258-48-6.mol

Synonyms:1-Hydroxy-5,8-dimethoxy-2-(3',4',6'-tri-O-benzyl-2'-deoxy-β-D-arabino-hexopyranosyl)naphthalene

Chemical Property of 1-Hydroxy-5,8-dimethoxy-2-(3',4',6'-tri-O-benzyl-2'-deoxy-β-D-arabino-hexopyranosyl)naphthalene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-Hydroxy-5,8-dimethoxy-2-(3',4',6'-tri-O-benzyl-2'-deoxy-β-D-arabino-hexopyranosyl)naphthalene

There total 7 articles about 1-Hydroxy-5,8-dimethoxy-2-(3',4',6'-tri-O-benzyl-2'-deoxy-β-D-arabino-hexopyranosyl)naphthalene 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: 81.0%

5,8-dimethoxynaphthalen-1-ol (91963-30-3) + 3,4,6-tri-O-benzyl-1-O-trifluoroacetyl-2-deoxy-D-glucopyranose (161258-46-4) → 1-Hydroxy-5,8-dimethoxy-2-(3',4',6'-tri-O-benzyl-2'-deoxy-β-D-arabino-hexopyranosyl)naphthalene (161258-48-6)

Guidance literature:

With boron trifluoride diethyl etherate; In acetonitrile; at 0 ℃;

DOI:10.1016/S0040-4039(00)78474-7

Reference yield: 73.0%

5,8-dimethoxynaphthalen-1-ol (91963-30-3) + 3,4,6-tri-O-benzyl-2-deoxy-1-O-acetyl-α/β-D-glucopyranose (264881-65-4) → 1-Hydroxy-5,8-dimethoxy-2-(3',4',6'-tri-O-benzyl-2'-deoxy-β-D-arabino-hexopyranosyl)naphthalene (161258-48-6)

Guidance literature:

With boron trifluoride diethyl etherate; In acetonitrile; at 0 ℃; for 0.333333h;

DOI:10.1016/S0040-4039(00)00289-6

Reference yield:

5-hydroxynaphtho-1,4-quinone (481-39-0) → 1-Hydroxy-5,8-dimethoxy-2-(3',4',6'-tri-O-benzyl-2'-deoxy-β-D-arabino-hexopyranosyl)naphthalene (161258-48-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / Ag₂O / CHCl₃

2: aq. Na₂S₂O₄ / CH₂Cl₂; diethyl ether / 0.17 h

3: 3.33 g / K₂CO₃ / acetone / 48 h / Heating

4: 98 percent / H₂ / 10percent Pd/C / ethyl acetate / 4 h

5: 73 percent / BF₃*Et₂O / acetonitrile / 0.33 h / 0 °C

With sodium dithionite; boron trifluoride diethyl etherate; hydrogen; potassium carbonate; silver(l) oxide; 10percent Pd/C; In diethyl ether; dichloromethane; chloroform; ethyl acetate; acetone; acetonitrile;

DOI:10.1039/b103080a

upstream raw materials:

5,8-dimethoxynaphthalen-1-ol

3,4,6-tri-O-benzyl-1-O-trifluoroacetyl-2-deoxy-D-glucopyranose

3,4,6-tri-O-benzyl-2-deoxy-1-O-acetyl-α/β-D-glucopyranose

5-hydroxynaphtho-1,4-quinone

Downstream raw materials:

6-Acetyl-5-hydroxy-4-methoxy-3-(3',4',6'-tri-O-benzyl-2'-deoxy-β-D-arabino-hexopyranosyl)-6b,9a-dihydrofuro[3,2-b]naphtho[2,1-d]furan-8(9H)-one

2-Acetyl-1,4,8-trimethoxy-7-(3',4',6'-tri-O-benzyl-2'-deoxy-β-D-arabino-hexopyranosyl)naphthalene

2-Bromo-1-hydroxy-4,8-dimethoxy-7-(3',4',6'-tri-O-benzyl-2'-deoxy-β-D-arabino-hexopyranosyl)naphthalene