methyl 3-benzyloxyamino-2,3,6-trideoxy-3-C-methyl-β-L-lyxo-hexopyranoside

Base Information

Chemical Name:methyl 3-benzyloxyamino-2,3,6-trideoxy-3-C-methyl-β-L-lyxo-hexopyranoside
CAS No.:172603-48-4
Molecular Formula:C₁₅H₂₃NO₄
Molecular Weight:281.352
Hs Code.:

Synonyms:methyl 3-benzyloxyamino-2,3,6-trideoxy-3-C-methyl-β-L-lyxo-hexopyranoside

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Chemical Property of methyl 3-benzyloxyamino-2,3,6-trideoxy-3-C-methyl-β-L-lyxo-hexopyranoside

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Technology Process of methyl 3-benzyloxyamino-2,3,6-trideoxy-3-C-methyl-β-L-lyxo-hexopyranoside

There total 8 articles about methyl 3-benzyloxyamino-2,3,6-trideoxy-3-C-methyl-β-L-lyxo-hexopyranoside 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: 56.0%

: (E)-methyl 2,6-dideoxy-β-L-threo-hexopyranosid-3-ulose O-benzyloxime

: (2S,3S)-3-Hydroxy-2-methyl-2,3-dihydro-pyran-4-one O-benzyl-oxime

: 172603-48-4
methyl 3-benzyloxyamino-2,3,6-trideoxy-3-C-methyl-β-L-lyxo-hexopyranoside

Guidance literature:: With cerium(III) chloride; methyllithium; In tetrahydrofuran; diethyl ether; at -78 - 0 ℃; for 3h;
DOI:10.1016/0008-6215(95)00066-3

Reference yield:

: 62346-15-0
methyl 2,6-dideoxy-β-L-lyxo-hexopyranoside

: 172603-48-4
methyl 3-benzyloxyamino-2,3,6-trideoxy-3-C-methyl-β-L-lyxo-hexopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) dibutyltin oxide, 2.) n-Bu₄NI, 3.) KF

2: 88 percent / pyridine / dimethylformamide / 17 h / Ambient temperature

3: 85 percent / 2,3-dichloro-5,6-dicyanobenzoquinone / CH₂Cl₂; H₂O / 2 h / Ambient temperature

4: 71 percent / pyridinium dichromate / CH₂Cl₂ / 4 h / Heating

5: NaOH / ethanol / 2 h / Ambient temperature

6: n-Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

7: 1.) CeCl₃ / 1.) THF, ether, -78 deg C, 1 h, 2.) THF, ether, a) -78 deg C, 2 h, b) 0 deg C, 1 h

With pyridine; potassium fluoride; sodium hydroxide; dipyridinium dichromate; cerium(III) chloride; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(95)00066-3

Reference yield:

: 172603-40-6
methyl 4-O-tert-butyldimethylsilyl-2,6-dideoxy-β-L-lyxo-hexopyranoside

: 172603-48-4
methyl 3-benzyloxyamino-2,3,6-trideoxy-3-C-methyl-β-L-lyxo-hexopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 71 percent / pyridinium dichromate / CH₂Cl₂ / 4 h / Heating

2: NaOH / ethanol / 2 h / Ambient temperature

3: n-Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

4: 1.) CeCl₃ / 1.) THF, ether, -78 deg C, 1 h, 2.) THF, ether, a) -78 deg C, 2 h, b) 0 deg C, 1 h

With sodium hydroxide; dipyridinium dichromate; cerium(III) chloride; tetrabutyl ammonium fluoride; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1016/0008-6215(95)00066-3