methyl 2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-6-O-methanesulfonyloxy-D-mannonate

Base Information

• Chemical Name: methyl 2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-6-O-methanesulfonyloxy-D-mannonate
• CAS No.: 160147-89-7
• Molecular Formula: C₁₉H₂₇NO₁₀S
• Molecular Weight: 461.49
• Mol file: 160147-89-7.mol

Synonyms:methyl 2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-6-O-methanesulfonyloxy-D-mannonate

Chemical Property of methyl 2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-6-O-methanesulfonyloxy-D-mannonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-6-O-methanesulfonyloxy-D-mannonate

There total 4 articles about methyl 2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-6-O-methanesulfonyloxy-D-mannonate 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: 78.0%

methanesulfonyl chloride (124-63-0) + methyl 2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-D-mannonate (160147-88-6) → methyl 2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-6-O-methanesulfonyloxy-D-mannonate (160147-89-7)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 0.166667h;

DOI:10.1039/P19940002621

Reference yield:

methyl 2-azido-2-deoxy-3,4:5,6-di-O-isopropylidene-D-mannonate (117462-55-2) → methyl 2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-6-O-methanesulfonyloxy-D-mannonate (160147-89-7)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / Pd-C / ethyl acetate / 6 h

2: aq. Na₂CO₃ / CH₂Cl₂ / 0.5 h / Ambient temperature

3: 95 percent / Dowex 50W-X₈ resin, water / methanol / 16 h / Ambient temperature; further catalysts and solvents

4: 78 percent / Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

With Dowex 50W-X₈ resin; water; hydrogen; sodium carbonate; triethylamine; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate;

DOI:10.1039/P19940002621

Reference yield:

methyl 3,4;5,6-di-O-isopropylidene-2-amino-2-deoxy-D-mannate (133473-08-2) → methyl 2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-6-O-methanesulfonyloxy-D-mannonate (160147-89-7)

Guidance literature:

Multi-step reaction with 3 steps

1: aq. Na₂CO₃ / CH₂Cl₂ / 0.5 h / Ambient temperature

2: 95 percent / Dowex 50W-X₈ resin, water / methanol / 16 h / Ambient temperature; further catalysts and solvents

3: 78 percent / Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

With Dowex 50W-X₈ resin; water; sodium carbonate; triethylamine; In methanol; dichloromethane;

DOI:10.1039/P19940002621

upstream raw materials:

methanesulfonyl chloride

methyl 2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-D-mannonate

methyl 3,4;5,6-di-O-isopropylidene-2-amino-2-deoxy-D-mannate

methyl 2-azido-2-deoxy-3,4:5,6-di-O-isopropylidene-D-mannonate

Downstream raw materials:

(2S,3R,4R,5R)-3,4,5-trihydroxypipecolic acid

1-deoxymannojirimycin