methyl N-benzyloxycarbonyl-3-O-benzyl-2,6-dideoxy-2,6-imino-5-O-phenyloxythiocarbonyl-α-D-mannofuranoside

Base Information

• Chemical Name: methyl N-benzyloxycarbonyl-3-O-benzyl-2,6-dideoxy-2,6-imino-5-O-phenyloxythiocarbonyl-α-D-mannofuranoside
• CAS No.: 113000-79-6
• Molecular Formula: C₂₉H₂₉NO₇S
• Molecular Weight: 535.618
• Mol file: 113000-79-6.mol

Synonyms:methyl N-benzyloxycarbonyl-3-O-benzyl-2,6-dideoxy-2,6-imino-5-O-phenyloxythiocarbonyl-α-D-mannofuranoside

Chemical Property of methyl N-benzyloxycarbonyl-3-O-benzyl-2,6-dideoxy-2,6-imino-5-O-phenyloxythiocarbonyl-α-D-mannofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl N-benzyloxycarbonyl-3-O-benzyl-2,6-dideoxy-2,6-imino-5-O-phenyloxythiocarbonyl-α-D-mannofuranoside

There total 1 articles about methyl N-benzyloxycarbonyl-3-O-benzyl-2,6-dideoxy-2,6-imino-5-O-phenyloxythiocarbonyl-α-D-mannofuranoside 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: 91.0%

methyl N-benzyloxycarbonyl-3-O-benzyl-2,6-dideoxy-2,6-imino-α-D-mannofuranoside (98260-67-4) + phenyl chlorothionocarbonate → methyl N-benzyloxycarbonyl-3-O-benzyl-2,6-dideoxy-2,6-imino-5-O-phenyloxythiocarbonyl-α-D-mannofuranoside (113000-79-6)

Guidance literature:

With dmap; In acetonitrile; for 24h; Ambient temperature;

DOI:10.1016/S0040-4020(01)90035-3

Reference yield: 76.0%

methyl N-benzyloxycarbonyl-3-O-benzyl-2,6-dideoxy-2,6-imino-5-O-phenyloxythiocarbonyl-α-D-mannofuranoside (113000-79-6) → methyl 3-O-benzyl-N-benzyloxycarbonyl-2,6-imino-2,5,6-trideoxy-α-D-lyxo-hexofuranoside (98260-66-3)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 75 ℃; for 24h;

DOI:10.1016/S0040-4020(01)90035-3

Reference yield:

methyl N-benzyloxycarbonyl-3-O-benzyl-2,6-dideoxy-2,6-imino-5-O-phenyloxythiocarbonyl-α-D-mannofuranoside (113000-79-6) → D-fagomine (53185-12-9,475630-67-2,637771-88-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 76 percent / azobisisobutyronitrile, tri-n-butyltin hydride / toluene / 24 h / 75 °C

2: 1.) 50percent aq. trifluoroacetic acid; 2.) sodium borohydride / 1.) 30 min.; 2.) ethanol, room temp., 1 h.

3: 74 percent / hydrogen / 10percent palladium hydroxide on charcoal / ethanol / 12 h

With sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); hydrogen; tri-n-butyl-tin hydride; trifluoroacetic acid; palladium hydroxide - carbon; In ethanol; toluene;

DOI:10.1016/S0040-4020(01)90035-3

upstream raw materials:

methyl N-benzyloxycarbonyl-3-O-benzyl-2,6-dideoxy-2,6-imino-α-D-mannofuranoside

Downstream raw materials:

methyl 3-O-benzyl-N-benzyloxycarbonyl-2,6-imino-2,5,6-trideoxy-α-D-lyxo-hexofuranoside

4-O-benzyl-N-benzyloxycarbonyl-1,5-imino-1,2,5-trideoxy-D-arabino-hexitol

D-fagomine