1,2-dideoxy-3,4:5,6-di-O-isopropylidene-2-[(9-phenyl-9-fluorenyl)-amino]-D-iditol

Base Information

• Chemical Name: 1,2-dideoxy-3,4:5,6-di-O-isopropylidene-2-[(9-phenyl-9-fluorenyl)-amino]-D-iditol
• CAS No.: 733038-16-9
• Molecular Formula: C₃₁H₃₅NO₄
• Molecular Weight: 485.623
• Mol file: 733038-16-9.mol

Synonyms:1,2-dideoxy-3,4:5,6-di-O-isopropylidene-2-[(9-phenyl-9-fluorenyl)-amino]-D-iditol

Chemical Property of 1,2-dideoxy-3,4:5,6-di-O-isopropylidene-2-[(9-phenyl-9-fluorenyl)-amino]-D-iditol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2-dideoxy-3,4:5,6-di-O-isopropylidene-2-[(9-phenyl-9-fluorenyl)-amino]-D-iditol

There total 4 articles about 1,2-dideoxy-3,4:5,6-di-O-isopropylidene-2-[(9-phenyl-9-fluorenyl)-amino]-D-iditol 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: 79.0%

(R)-1-((4R,5S,4'R)-2,2,2',2'-Tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-ethylamine + 9-bromo-9-phenyl-9H-fluorene (55135-66-5) → 1,2-dideoxy-3,4:5,6-di-O-isopropylidene-2-[(9-phenyl-9-fluorenyl)-amino]-D-iditol (733038-16-9)

Guidance literature:

With lead(II) nitrate; triethylamine; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1271/bbb.68.714

Reference yield:

1-deoxy-3,4:5,6-di-O-isopropylidene-D-gulitol (733752-82-4) → 1,2-dideoxy-3,4:5,6-di-O-isopropylidene-2-[(9-phenyl-9-fluorenyl)-amino]-D-iditol (733038-16-9)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / CH₂Cl₂ / 0.17 h / -10 °C

2: 0.65 g / sodium azide / dimethylformamide / 2 h / 20 °C

3: 85 percent / hydrogen / palladium on carbon / ethyl acetate / 20 °C

4: 79 percent / Pb(NO₃)2; triethylamine / CH₂Cl₂ / 24 h / 20 °C

With pyridine; sodium azide; lead(II) nitrate; hydrogen; triethylamine; palladium on activated charcoal; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1271/bbb.68.714

Reference yield:

Trifluoro-methanesulfonic acid (S)-1-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-ethyl ester (733038-30-7) → 1,2-dideoxy-3,4:5,6-di-O-isopropylidene-2-[(9-phenyl-9-fluorenyl)-amino]-D-iditol (733038-16-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 0.65 g / sodium azide / dimethylformamide / 2 h / 20 °C

2: 85 percent / hydrogen / palladium on carbon / ethyl acetate / 20 °C

3: 79 percent / Pb(NO₃)2; triethylamine / CH₂Cl₂ / 24 h / 20 °C

With sodium azide; lead(II) nitrate; hydrogen; triethylamine; palladium on activated charcoal; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1271/bbb.68.714

upstream raw materials:

9-bromo-9-phenyl-9H-fluorene

1-deoxy-3,4:5,6-di-O-isopropylidene-D-gulitol

Trifluoro-methanesulfonic acid (S)-1-((4S,5R,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-ethyl ester

1,2-anhydro-3,4,5,6-di-O-isopropylidene-D-gulitol

Downstream raw materials:

1,2-dideoxy-3,4-O-isopropylidene-5-O-methanesulfonyl-2-[(9-phenyl-9-fluorenyl)-amino]-L-xylitol

1,2,5-trideoxy-3,4-O-isopropylidene-5-iodo-2-[(9-phenyl-9-fluorenyl)-amino]-L-xylitol

1,2-dideoxy-3,4-O-isopropylidene-2-[(9-phenyl-9-fluorenyl)-amino]-L-xylitol

(3R,4R)-3-benzyloxy-4-[(9-phenyl-9-fluorenyl)-amino]-1-pentene