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

Base Information

• Chemical Name: 2-Acetyl-7-(3',4',6'-tri-O-benzyl-2'-deoxy-β-D-arabino-hexopyranosyl)-8-methoxy-1,4-naphthoquinone
• CAS No.: 282723-42-6
• Molecular Formula: C₄₀H₃₈O₈
• Molecular Weight: 646.737
• Mol file: 282723-42-6.mol

Synonyms:2-Acetyl-7-(3',4',6'-tri-O-benzyl-2'-deoxy-β-D-arabino-hexopyranosyl)-8-methoxy-1,4-naphthoquinone

Chemical Property of 2-Acetyl-7-(3',4',6'-tri-O-benzyl-2'-deoxy-β-D-arabino-hexopyranosyl)-8-methoxy-1,4-naphthoquinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Acetyl-7-(3',4',6'-tri-O-benzyl-2'-deoxy-β-D-arabino-hexopyranosyl)-8-methoxy-1,4-naphthoquinone

There total 15 articles about 2-Acetyl-7-(3',4',6'-tri-O-benzyl-2'-deoxy-β-D-arabino-hexopyranosyl)-8-methoxy-1,4-naphthoquinone 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: 93.0%

2-Acetyl-1,4,8-trimethoxy-7-(3',4',6'-tri-O-benzyl-2'-deoxy-β-D-arabino-hexopyranosyl)naphthalene (282723-49-3) → 2-Acetyl-7-(3',4',6'-tri-O-benzyl-2'-deoxy-β-D-arabino-hexopyranosyl)-8-methoxy-1,4-naphthoquinone (282723-42-6)

Guidance literature:

With silver(II) oxide; nitric acid; In 1,4-dioxane; for 0.333333h;

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

Reference yield:

5,8-dimethoxynaphthalen-1-ol (91963-30-3) → 2-Acetyl-7-(3',4',6'-tri-O-benzyl-2'-deoxy-β-D-arabino-hexopyranosyl)-8-methoxy-1,4-naphthoquinone (282723-42-6)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 73 percent / BF₃*Et₂O / acetonitrile / 0.33 h / 0 °C

2.1: NaH / dimethylformamide / 0.08 h / 0 °C

2.2: 85 percent / dimethylformamide / 12 h / 0 - 20 °C

3.1: 93 percent / aq. CAN / acetonitrile / 0.5 h

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

5.1: 643 mg / K₂CO₃ / acetone / Heating

6.1: 77 percent / Br₂ / CCl₄ / 0.03 h / 0 °C

7.1: 84 percent / aq. NaOH / dimethylformamide / 0.5 h / 20 °C

8.1: Pd(PPh₃)2Cl₂ / toluene / 18 h / 100 °C

9.1: 95 mg / aq. HCl / toluene; CH₂Cl₂ / 0.5 h

10.1: 93 percent / AgO; HNO₃ / dioxane / 0.33 h

With hydrogenchloride; silver(II) oxide; sodium hydroxide; sodium dithionite; ammonium cerium(IV) nitrate; boron trifluoride diethyl etherate; bromine; nitric acid; sodium hydride; potassium carbonate; bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; tetrachloromethane; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 8.1: Stille coupling;

DOI:10.1039/b103080a

Reference yield:

1-Hydroxy-5,8-dimethoxy-2-(3',4',6'-tri-O-benzyl-2'-deoxy-β-D-arabino-hexopyranosyl)naphthalene (161258-48-6) → 2-Acetyl-7-(3',4',6'-tri-O-benzyl-2'-deoxy-β-D-arabino-hexopyranosyl)-8-methoxy-1,4-naphthoquinone (282723-42-6)

Guidance literature:

Multi-step reaction with 9 steps

1.1: NaH / dimethylformamide / 0.08 h / 0 °C

1.2: 85 percent / dimethylformamide / 12 h / 0 - 20 °C

2.1: 93 percent / aq. CAN / acetonitrile / 0.5 h

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

4.1: 643 mg / K₂CO₃ / acetone / Heating

5.1: 77 percent / Br₂ / CCl₄ / 0.03 h / 0 °C

6.1: 84 percent / aq. NaOH / dimethylformamide / 0.5 h / 20 °C

7.1: Pd(PPh₃)2Cl₂ / toluene / 18 h / 100 °C

8.1: 95 mg / aq. HCl / toluene; CH₂Cl₂ / 0.5 h

9.1: 93 percent / AgO; HNO₃ / dioxane / 0.33 h

With hydrogenchloride; silver(II) oxide; sodium hydroxide; sodium dithionite; ammonium cerium(IV) nitrate; bromine; nitric acid; sodium hydride; potassium carbonate; bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; tetrachloromethane; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 7.1: Stille coupling;

DOI:10.1039/b103080a

upstream raw materials:

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

5-hydroxynaphtho-1,4-quinone

5,8-dimethoxynaphthalen-1-ol

5-(benzyloxy)-1,4-dihydronaphthalene-1,4-dione

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