(3S,4S,5R)-4,5-Bis-benzoyloxy-3-benzoyloxymethyl-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (3S,4S,5R)-4,5-Bis-benzoyloxy-3-benzoyloxymethyl-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester
• CAS No.: 204992-81-4
• Molecular Formula: C₃₂H₃₃NO₉
• Molecular Weight: 575.615

Synonyms:(3S,4S,5R)-4,5-Bis-benzoyloxy-3-benzoyloxymethyl-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester

Chemical Property of (3S,4S,5R)-4,5-Bis-benzoyloxy-3-benzoyloxymethyl-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (3S,4S,5R)-4,5-Bis-benzoyloxy-3-benzoyloxymethyl-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester

There total 9 articles about (3S,4S,5R)-4,5-Bis-benzoyloxy-3-benzoyloxymethyl-3-hydroxy-piperidine-1-carboxylic acid tert-butyl 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:

(3aS,6R,6aS)-6-(hydroxymethyl)-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-ol (4099-88-1,67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1) → (3S,4S,5R)-4,5-Bis-benzoyloxy-3-benzoyloxymethyl-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (204992-81-4)

Guidance literature:

Multi-step reaction with 8 steps

1: pyridine / Ambient temperature

2: 1 h / 0 - 5 °C

3: NaN₃ / dimethylformamide / 120 °C

4: NaOMe, MeOH / 0.5 h / Ambient temperature

5: K₂CO₃ / H₂O; methanol / 24 h / 85 °C

6: 1N aq. HCl / methanol / Ambient temperature

7: methanol / Ambient temperature

8: pyridine / Ambient temperature

With pyridine; hydrogenchloride; methanol; sodium azide; sodium methylate; potassium carbonate; In methanol; water; N,N-dimethyl-formamide;

DOI:10.1021/ja973443k

Reference yield:

D-lyxose (87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2) → (3S,4S,5R)-4,5-Bis-benzoyloxy-3-benzoyloxymethyl-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (204992-81-4)

Guidance literature:

Multi-step reaction with 9 steps

1: H₂SO₄ / Ambient temperature

2: pyridine / Ambient temperature

3: 1 h / 0 - 5 °C

4: NaN₃ / dimethylformamide / 120 °C

5: NaOMe, MeOH / 0.5 h / Ambient temperature

6: K₂CO₃ / H₂O; methanol / 24 h / 85 °C

7: 1N aq. HCl / methanol / Ambient temperature

8: methanol / Ambient temperature

9: pyridine / Ambient temperature

With pyridine; hydrogenchloride; methanol; sodium azide; sulfuric acid; sodium methylate; potassium carbonate; In methanol; water; N,N-dimethyl-formamide;

DOI:10.1021/ja973443k

Reference yield:

1-O-benzoyl-2,3-O-isopropylidene-5-O-(p-tolylsulfonyl)-α-D-lyxofuranose (110808-29-2) → (3S,4S,5R)-4,5-Bis-benzoyloxy-3-benzoyloxymethyl-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (204992-81-4)

Guidance literature:

Multi-step reaction with 6 steps

1: NaN₃ / dimethylformamide / 120 °C

2: NaOMe, MeOH / 0.5 h / Ambient temperature

3: K₂CO₃ / H₂O; methanol / 24 h / 85 °C

4: 1N aq. HCl / methanol / Ambient temperature

5: methanol / Ambient temperature

6: pyridine / Ambient temperature

With pyridine; hydrogenchloride; methanol; sodium azide; sodium methylate; potassium carbonate; In methanol; water; N,N-dimethyl-formamide;

DOI:10.1021/ja973443k

upstream raw materials:

benzoyl chloride

(3aS,6R,6aS)-6-(hydroxymethyl)-2,2-dimethyl-tetrahydrofuro[3,4-d]-[1,3]dioxol-4-ol

D-lyxose

1-O-benzoyl-2,3-O-isopropylidene-5-O-(p-tolylsulfonyl)-α-D-lyxofuranose

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