5-O-Benzyl-3-chloro-2,3-didesoxy-2-dimethylamino-β-D-arabinofuranoside de methyle

Base Information

• Chemical Name: 5-O-Benzyl-3-chloro-2,3-didesoxy-2-dimethylamino-β-D-arabinofuranoside de methyle
• CAS No.: 143604-34-6
• Molecular Formula: C₁₅H₂₂ClNO₃
• Molecular Weight: 299.798
• Mol file: 143604-34-6.mol

Synonyms:5-O-Benzyl-3-chloro-2,3-didesoxy-2-dimethylamino-β-D-arabinofuranoside de methyle

Chemical Property of 5-O-Benzyl-3-chloro-2,3-didesoxy-2-dimethylamino-β-D-arabinofuranoside de methyle

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-O-Benzyl-3-chloro-2,3-didesoxy-2-dimethylamino-β-D-arabinofuranoside de methyle

There total 8 articles about 5-O-Benzyl-3-chloro-2,3-didesoxy-2-dimethylamino-β-D-arabinofuranoside de methyle 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: 23.0%

5-O-Benzyl-3-desoxy-3-dimethylamino-2-O-methanesulfonyl-β-D-xylofuranoside de methyle (143604-43-7) → 5-O-Benzyl-3-chloro-2,3-didesoxy-2-dimethylamino-β-D-arabinofuranoside de methyle (143604-34-6) + 5-O-Benzyl-2-chloro-2,3-didesoxy-3-dimethylamino-β-D-xylofuranoside de methyle (143604-33-5)

Guidance literature:

With triethylamine hydrochloride; In acetonitrile; at 80 ℃; for 1.5h;

DOI:10.1016/S0040-4020(01)90122-X

Reference yield:

2,3-Anhydro-5-O-benzyl-β-D-ribofuranoside de methyle (20535-09-5) → 5-O-Benzyl-3-chloro-2,3-didesoxy-2-dimethylamino-β-D-arabinofuranoside de methyle (143604-34-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 22 percent / H₂O / 96 h / 100 °C

2: 97 percent / Et₃N / CH₂Cl₂ / 1.5 h / -30 °C

3: CD₃CN, D₂O / 2 h / 75 °C

4: H₂O / 20 h / 70 °C

5: 100 percent / Et₃N / CH₂Cl₂ / 2.5 h / -30 °C

6: 51 percent / Et₃N*HCl / acetonitrile / 1.5 h / 80 °C

With [D₃]acetonitrile; water; water-d2; triethylamine hydrochloride; triethylamine; In dichloromethane; water; acetonitrile;

DOI:10.1016/S0040-4020(01)90122-X

Reference yield:

benzyl bromide (100-39-0) → 5-O-Benzyl-3-chloro-2,3-didesoxy-2-dimethylamino-β-D-arabinofuranoside de methyle (143604-34-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 98 percent / NaH / tetrahydrofuran / 2.5 h

2: 22 percent / H₂O / 96 h / 100 °C

3: 97 percent / Et₃N / CH₂Cl₂ / 1.5 h / -30 °C

4: CD₃CN, D₂O / 2 h / 75 °C

5: H₂O / 20 h / 70 °C

6: 100 percent / Et₃N / CH₂Cl₂ / 2.5 h / -30 °C

7: 51 percent / Et₃N*HCl / acetonitrile / 1.5 h / 80 °C

With [D₃]acetonitrile; water; water-d2; triethylamine hydrochloride; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; water; acetonitrile;

DOI:10.1016/S0040-4020(01)90122-X

upstream raw materials:

5-O-Benzyl-3-desoxy-3-dimethylamino-2-O-methanesulfonyl-β-D-xylofuranoside de methyle

2,3-Anhydro-5-O-benzyl-β-D-ribofuranoside de methyle

benzyl bromide

Methanesulfonate(1R,2S,4R,5S)-2-benzyloxymethyl-4-methoxy-6,6-dimethyl-3-oxa-6-azonia-bicyclo[3.1.0]hexane;