2-chloro-6-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-5-methoxy-1,4-naphthoquinone

Base Information

• Chemical Name: 2-chloro-6-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-5-methoxy-1,4-naphthoquinone
• CAS No.: 171081-05-3
• Molecular Formula: C₃₁H₂₉ClO₆
• Molecular Weight: 533.021
• Mol file: 171081-05-3.mol

Synonyms:2-chloro-6-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-5-methoxy-1,4-naphthoquinone

Chemical Property of 2-chloro-6-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-5-methoxy-1,4-naphthoquinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-chloro-6-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-5-methoxy-1,4-naphthoquinone

There total 12 articles about 2-chloro-6-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-5-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%

6-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-5-methoxy-1,4-naphthoquinone (171081-04-2) → 2-chloro-6-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-5-methoxy-1,4-naphthoquinone (171081-05-3)

Guidance literature:

6-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-5-methoxy-1,4-naphthoquinone; With chlorine; acetic acid;

With ethanol; at 75 ℃;

DOI:10.1016/S0040-4039(02)02666-7

Reference yield:

6-((2R,4R,5R,6R)-4,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-4-(tert-butyl-dimethyl-silanyloxy)-2-chloro-5-methoxy-naphthalen-1-ol → 2-chloro-6-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-5-methoxy-1,4-naphthoquinone (171081-05-3)

Guidance literature:

With ammonium cerium(IV) nitrate; In tetrahydrofuran; water; acetonitrile; at 0 ℃; for 0.5h;

DOI:10.1016/S0040-4020(97)01034-X

Reference yield:

2-((2R,4R,5R,6R)-4,5-bis(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yl)-5,8-dimethoxynaphthalen-1-ol (551939-59-4) → 2-chloro-6-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-5-methoxy-1,4-naphthoquinone (171081-05-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaH / dimethylformamide

2.1: CAN / acetonitrile; H₂O

3.1: Cl₂; HOAc

3.2: 93 percent / EtOH / 75 °C

With ammonium cerium(IV) nitrate; chlorine; sodium hydride; acetic acid; In water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4039(02)02666-7

upstream raw materials:

2-(tert-butyldimethylsilyloxy)-4-chlorofuran

4-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-2-iodo-3-methoxyphenyl trifluoromethanesulfonate

6-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-5-methoxy-1,4-naphthoquinone

2-((2R,4R,5R,6R)-4,5-bis(benzyloxy)-6-methyltetrahydro-2H-pyran-2-yl)-5,8-dimethoxynaphthalen-1-ol

Downstream raw materials:

2-(3,4-di-O-benzyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-10-benzyloxy-6-hydroxy-1-methoxy-8-methylnaphthacene-5,12-dione