5,8-benzyloxycarbonylimino-5,6,7,8-tetradeoxy-1,2-O-isopropylidene-α-D-octofuranosid-3-ulose-hydrate

Base Information

• Chemical Name: 5,8-benzyloxycarbonylimino-5,6,7,8-tetradeoxy-1,2-O-isopropylidene-α-D-octofuranosid-3-ulose-hydrate
• CAS No.: 144691-15-6
• Molecular Formula: C₁₉H₂₅NO₇
• Molecular Weight: 379.41
• Mol file: 144691-15-6.mol

Synonyms:5,8-benzyloxycarbonylimino-5,6,7,8-tetradeoxy-1,2-O-isopropylidene-α-D-octofuranosid-3-ulose-hydrate

Chemical Property of 5,8-benzyloxycarbonylimino-5,6,7,8-tetradeoxy-1,2-O-isopropylidene-α-D-octofuranosid-3-ulose-hydrate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5,8-benzyloxycarbonylimino-5,6,7,8-tetradeoxy-1,2-O-isopropylidene-α-D-octofuranosid-3-ulose-hydrate

There total 1 articles about 5,8-benzyloxycarbonylimino-5,6,7,8-tetradeoxy-1,2-O-isopropylidene-α-D-octofuranosid-3-ulose-hydrate 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: 75.0%

5,6,7,8-tetradeoxy-5,8-(N-benzyloxycarbonylimino)-1,2-O-isopropylidene-α-D-gluco-oct-1,4-furanose (115438-59-0) → 5,8-benzyloxycarbonylimino-5,6,7,8-tetradeoxy-1,2-O-isopropylidene-α-D-octofuranosid-3-ulose-hydrate (144691-15-6)

Guidance literature:

With phosphorus pentoxide; dimethyl sulfoxide; In N,N-dimethyl-formamide; at 65 - 70 ℃; for 2.5h;

DOI:10.1016/S0040-4020(01)86601-1

Reference yield: 78.0%

5,8-benzyloxycarbonylimino-5,6,7,8-tetradeoxy-1,2-O-isopropylidene-α-D-octofuranosid-3-ulose-hydrate (144691-15-6) → 5,8-benzyloxycarbonylimino-5,6,7,8-tetradeoxy-1,2-O-isopropylidene-α-D-allo-octose (144733-17-5)

Guidance literature:

With sodium tetrahydroborate; In ethanol; for 2h; Ambient temperature;

DOI:10.1016/S0040-4020(01)86601-1

Reference yield:

5,8-benzyloxycarbonylimino-5,6,7,8-tetradeoxy-1,2-O-isopropylidene-α-D-octofuranosid-3-ulose-hydrate (144691-15-6) → (R)-2-((2R,3R,4S)-3-Fluoro-4,5-dihydroxy-tetrahydro-furan-2-yl)-pyrrolidine-1-carboxylic acid benzyl ester

Guidance literature:

Multi-step reaction with 4 steps

1: 78 percent / NaBH₄ / aq. ethanol / 2 h / Ambient temperature

2: pyridine / CH₂Cl₂ / 0.33 h

3: tris-(dimethylamino)-sulfonium-difluoromethylsilicate (TASF) / CH₂Cl₂ / 1 h

4: Amberlite IR-120(H+)resin / H₂O / 3 h / 45 °C

With pyridine; sodium tetrahydroborate; Amberlite IR-120(H+)resin; tris(dimethylamino)sulfonium trimethylsilyldifluoride; In ethanol; dichloromethane; water;

DOI:10.1016/S0040-4020(01)86601-1

upstream raw materials:

5,6,7,8-tetradeoxy-5,8-(N-benzyloxycarbonylimino)-1,2-O-isopropylidene-α-D-gluco-oct-1,4-furanose

Downstream raw materials:

5,8-benzyloxycarbonylimino-5,6,7,8-tetradeoxy-1,2-O-isopropylidene-α-D-allo-octose

(R)-2-((2R,3S,4R)-3,4,5-Trihydroxy-tetrahydro-furan-2-yl)-pyrrolidine-1-carboxylic acid benzyl ester

5,8-benzyloxycarbonylimino-3,5,6,7,8-tetradeoxy-3-fluoro-1,2-O-isopropylidene-α-D-gluco-octose