(2S,3R,4R)-3-Benzyloxy-2-formyl-4-hydroxy-piperidine-1-carboxylic acid benzyl ester

Base Information

Chemical Name:(2S,3R,4R)-3-Benzyloxy-2-formyl-4-hydroxy-piperidine-1-carboxylic acid benzyl ester
CAS No.:131053-26-4
Molecular Formula:C₂₁H₂₃NO₅
Molecular Weight:369.417
Hs Code.:

Synonyms:(2S,3R,4R)-3-Benzyloxy-2-formyl-4-hydroxy-piperidine-1-carboxylic acid benzyl ester

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Chemical Property of (2S,3R,4R)-3-Benzyloxy-2-formyl-4-hydroxy-piperidine-1-carboxylic acid benzyl ester

Chemical Property:

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Technology Process of (2S,3R,4R)-3-Benzyloxy-2-formyl-4-hydroxy-piperidine-1-carboxylic acid benzyl ester

There total 12 articles about (2S,3R,4R)-3-Benzyloxy-2-formyl-4-hydroxy-piperidine-1-carboxylic acid benzyl ester 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:

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

: 131053-26-4
(2S,3R,4R)-3-Benzyloxy-2-formyl-4-hydroxy-piperidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: methanol / Dowex 50W-X₈ resin (H⁺ form) / Heating

2: pyridine / CH₂Cl₂ / 0.33 h / -20 °C

3: NaN₃ / dimethylformamide / 48 h / 50 °C

4: methanol / sodium methylate / Ambient temperature

5: pyridine / 6 h / Ambient temperature

7: pyridine / -20 °C

8: 1) lithium triethylborohydride, 2) benzyl chloroformate / 1) tetrahydrofuran

9: H₂O / CF₃COOH / 1 h / Ambient temperature

With pyridine; methanol; sodium azide; water; lithium triethylborohydride; benzyl chloroformate; Dowex 50W-X₈ resin (H⁺ form); sodium methylate; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)99073-7

Reference yield:

: 16895-87-7
methyl-3-O-benzyl-α-D-glucofuranoside-5,6-carbonate

: 131053-26-4
(2S,3R,4R)-3-Benzyloxy-2-formyl-4-hydroxy-piperidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: pyridine / CH₂Cl₂ / 0.33 h / -20 °C

2: NaN₃ / dimethylformamide / 48 h / 50 °C

3: methanol / sodium methylate / Ambient temperature

4: pyridine / 6 h / Ambient temperature

6: pyridine / -20 °C

7: 1) lithium triethylborohydride, 2) benzyl chloroformate / 1) tetrahydrofuran

8: H₂O / CF₃COOH / 1 h / Ambient temperature

With pyridine; methanol; sodium azide; water; lithium triethylborohydride; benzyl chloroformate; sodium methylate; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)99073-7

Reference yield:

: 22529-61-9
(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

: 131053-26-4
(2S,3R,4R)-3-Benzyloxy-2-formyl-4-hydroxy-piperidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: sodium methoxide / Heating

2: methanol / Dowex 50W-X₈ resin (H⁺ form) / Heating

3: pyridine / CH₂Cl₂ / 0.33 h / -20 °C

4: NaN₃ / dimethylformamide / 48 h / 50 °C

5: methanol / sodium methylate / Ambient temperature

6: pyridine / 6 h / Ambient temperature

8: pyridine / -20 °C

9: 1) lithium triethylborohydride, 2) benzyl chloroformate / 1) tetrahydrofuran

10: H₂O / CF₃COOH / 1 h / Ambient temperature

With pyridine; methanol; sodium azide; water; sodium methylate; lithium triethylborohydride; benzyl chloroformate; Dowex 50W-X₈ resin (H⁺ form); sodium methylate; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)99073-7