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

Base Information

Chemical Name:methyl N-benzyloxycarbonyl-3-O-benzyl-2,5-dideoxy-2,5-imino-α-D-mannofuranoside
CAS No.:98260-70-9
Molecular Formula:C₂₂H₂₅NO₆
Molecular Weight:399.444
Hs Code.:

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

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

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

There total 16 articles about methyl N-benzyloxycarbonyl-3-O-benzyl-2,5-dideoxy-2,5-imino-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:

: 927705-78-0
(1R,3S,4S,6R,7R)-7-Benzyloxy-6-t-butyldimethylsilyloxymethyl-3-methoxy-2-oxa-5-aza-bicyclo[2.2.1]heptane-5-carboxylic acid benzyl ester

: 98260-70-9
methyl N-benzyloxycarbonyl-3-O-benzyl-2,5-dideoxy-2,5-imino-α-D-mannofuranoside

Guidance literature:: With trifluoroacetic acid; at 20 ℃; for 0.25h;

Reference yield:

: 16895-86-6
3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose-5,6-carbonate

: 98260-70-9
methyl N-benzyloxycarbonyl-3-O-benzyl-2,5-dideoxy-2,5-imino-α-D-mannofuranoside

Guidance literature:: Multi-step reaction with 10 steps

1: acid resin (Dowex 50W-XH) / methanol / 12 h / Heating

2: pyridine / CH₂Cl₂; pyridine / 0.25 h / -30 °C

3: sodium azide / dimethylformamide / 24 h / 50 °C

4: 80 percent / sodium metoxide / methanol / 6 h / Ambient temperature

5: 81 percent / pyridine / 4 h / from 0 deg C to room temp.

6: 94 percent / pyridine / 4 h / Ambient temperature

7: 82 percent / sodium methoxide / dimethylformamide / 0.08 h / 50 °C

8: sodium methoxide / dimethylformamide / 3 h / 50 °C

9: hydrogen / palladium black / ethanol / 1 h

10: aq. sodium bicarbonate / diethyl ether / 2 h / Ambient temperature

With pyridine; sodium azide; acid resin (Dowex 50W-XH); hydrogen; sodium methylate; sodium hydrogencarbonate; palladium; In pyridine; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)90034-1

Reference yield:

: 18685-18-2
3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose

: 98260-70-9
methyl N-benzyloxycarbonyl-3-O-benzyl-2,5-dideoxy-2,5-imino-α-D-mannofuranoside

Guidance literature:: Multi-step reaction with 12 steps

1: hydrochloric acid / methanol; H₂O / 20 h / Ambient temperature

2: sodium methoxide / 3 h / Heating

3: acid resin (Dowex 50W-XH) / methanol / 12 h / Heating

4: pyridine / CH₂Cl₂; pyridine / 0.25 h / -30 °C

5: sodium azide / dimethylformamide / 24 h / 50 °C

6: 80 percent / sodium metoxide / methanol / 6 h / Ambient temperature

7: 81 percent / pyridine / 4 h / from 0 deg C to room temp.

8: 94 percent / pyridine / 4 h / Ambient temperature

9: 82 percent / sodium methoxide / dimethylformamide / 0.08 h / 50 °C

10: sodium methoxide / dimethylformamide / 3 h / 50 °C

11: hydrogen / palladium black / ethanol / 1 h

12: aq. sodium bicarbonate / diethyl ether / 2 h / Ambient temperature

With pyridine; hydrogenchloride; sodium azide; acid resin (Dowex 50W-XH); hydrogen; sodium methylate; sodium hydrogencarbonate; palladium; In pyridine; methanol; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)90034-1