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

Base Information

• Chemical Name: methyl 2-benzyloxycarbonylamino-2-deoxy-3,4:5,6-di-O-isopropylidene-D-mannonate
• CAS No.: 160147-87-5
• Molecular Formula: C₂₁H₂₉NO₈
• Molecular Weight: 423.463

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

Chemical Property of methyl 2-benzyloxycarbonylamino-2-deoxy-3,4:5,6-di-O-isopropylidene-D-mannonate

Chemical Property:

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Technology Process of methyl 2-benzyloxycarbonylamino-2-deoxy-3,4:5,6-di-O-isopropylidene-D-mannonate

There total 2 articles about methyl 2-benzyloxycarbonylamino-2-deoxy-3,4:5,6-di-O-isopropylidene-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:

methyl 2-azido-2-deoxy-3,4:5,6-di-O-isopropylidene-D-mannonate (117462-55-2) → methyl 2-benzyloxycarbonylamino-2-deoxy-3,4:5,6-di-O-isopropylidene-D-mannonate (160147-87-5)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Pd-C / ethyl acetate / 6 h

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

With hydrogen; sodium carbonate; palladium on activated charcoal; In 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) + benzyl chloroformate (501-53-1,94274-21-2) → methyl 2-benzyloxycarbonylamino-2-deoxy-3,4:5,6-di-O-isopropylidene-D-mannonate (160147-87-5)

Guidance literature:

With sodium carbonate; In dichloromethane; for 0.5h; Yield given; Ambient temperature;

DOI:10.1039/P19940002621

Reference yield: 96.0%

methyl 2-benzyloxycarbonylamino-2-deoxy-3,4:5,6-di-O-isopropylidene-D-mannonate (160147-87-5) → methyl 2-benzyloxycarbonylamino-2-deoxy-3,4-O-isopropylidene-D-mannonate (160147-88-6)

Guidance literature:

With Dowex 50W-X₈ (110 W/Wpercent); In methanol; water; for 27h; Ambient temperature;

DOI:10.1016/0040-4039(94)88373-4

upstream raw materials:

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

benzyl chloroformate

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

Downstream raw materials:

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

(S)-Benzyloxycarbonylamino-{(4R,5R)-5-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-acetic acid methyl ester

Methanesulfonic acid (R)-1-[(4S,5R)-5-((R)-1-benzyloxycarbonylamino-2-hydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-(tert-butyl-dimethyl-silanyloxy)-ethyl ester

(S)-Benzyloxycarbonylamino-{(4R,5S)-5-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-methanesulfonyloxy-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-acetic acid methyl ester

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