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

Base Information

• Chemical Name: methyl 2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-D-gluconate
• CAS No.: 170997-53-2
• Molecular Formula: C₁₈H₂₅NO₈
• Molecular Weight: 383.398
• Mol file: 170997-53-2.mol

Synonyms:methyl 2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-D-gluconate

Chemical Property of methyl 2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-D-gluconate

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-D-gluconate

There total 1 articles about methyl 2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-D-gluconate 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: 93.0%

methyl 2-benzyloxycarbonylamino-2-deoxy-3,4;5,6-di-O-isopropylidene-D-gluconate (170997-52-1) → methyl 2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-D-gluconate (170997-53-2)

Guidance literature:

With Dowex 50W-X₈ resin; In methanol; water; for 52h; Ambient temperature;

Reference yield: 94.0%

tert-butyldimethylsilyl chloride (18162-48-6) + methyl 2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-D-gluconate (170997-53-2) → methyl 2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-6-O-(tert-butyldimethylsilyl)oxy-D-gluconate (170997-54-3)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 10h; Ambient temperature;

Reference yield:

methyl 2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-D-gluconate (170997-53-2) → 2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-5-O-methanesulfonyloxy-6-O-(tert-butyldimethylsilyl)oxy-D-glucitol (171228-71-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / imidazole / dimethylformamide / 10 h / Ambient temperature

2: 97 percent / Et₃N / tetrahydrofuran / 1 h / 0 °C

3: 90 percent / LiAlH₄ / tetrahydrofuran / 3 h / Ambient temperature

With 1H-imidazole; lithium aluminium tetrahydride; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide;

upstream raw materials:

methyl 2-benzyloxycarbonylamino-2-deoxy-3,4;5,6-di-O-isopropylidene-D-gluconate

Downstream raw materials:

methyl 2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-6-O-(tert-butyldimethylsilyl)oxy-D-gluconate

2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-5-O-methanesulfonyloxy-6-O-(tert-butyldimethylsilyl)oxy-D-glucitol

methyl 2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-5-O-methanesulfonyloxy-6-O-(tert-butyldimethylsilyl)oxy-D-gluconate