(2R,3S,4R,5S)-3,4,5-Trihydroxy-2-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester

Base Information

Chemical Name:(2R,3S,4R,5S)-3,4,5-Trihydroxy-2-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester
CAS No.:172139-94-5
Molecular Formula:C₁₄H₁₉NO₆
Molecular Weight:297.308
Hs Code.:

Synonyms:(2R,3S,4R,5S)-3,4,5-Trihydroxy-2-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester

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Chemical Property of (2R,3S,4R,5S)-3,4,5-Trihydroxy-2-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester

Chemical Property:

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Technology Process of (2R,3S,4R,5S)-3,4,5-Trihydroxy-2-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester

There total 7 articles about (2R,3S,4R,5S)-3,4,5-Trihydroxy-2-hydroxymethyl-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:

: 172033-94-2
1,5-benzyloxycarbonylimino-6-O-tert-butyldiphenylsilyl-1,5-dideoxy-D-galactitol

: 172139-94-5
(2R,3S,4R,5S)-3,4,5-Trihydroxy-2-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; for 2h; Ambient temperature;
DOI:10.1016/0008-6215(95)00068-5

Reference yield:

: 138381-83-6
4,6-O-(R-Benzylidene)-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-glucitol

: 172139-94-5
(2R,3S,4R,5S)-3,4,5-Trihydroxy-2-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / pyridine

2: 100 percent / 80percent aq. AcOH / 6 h / 45 °C

3: 93 percent / pyridine / 20 °C

4: pyridine / CH₂Cl₂ / 3 h / -15 °C

5: 18-crown-6 / acetonitrile / Ambient temperature

6: 100 percent / NaOCH₃ / methanol / 2.5 h / 0 °C

7: 215 mg / BF₃*Et₂O / CH₂Cl₂ / 2 h / Ambient temperature

With pyridine; 18-crown-6 ether; boron trifluoride diethyl etherate; sodium methylate; acetic acid; In methanol; dichloromethane; acetonitrile;
DOI:10.1016/0008-6215(95)00068-5

Reference yield:

: 153373-53-6
2,3-di-O-acetyl-1,5-benzyloxycarbonylimino-1,5-dideoxy-D-glucitol

: 172139-94-5
(2R,3S,4R,5S)-3,4,5-Trihydroxy-2-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 93 percent / pyridine / 20 °C

2: pyridine / CH₂Cl₂ / 3 h / -15 °C

3: 18-crown-6 / acetonitrile / Ambient temperature

4: 100 percent / NaOCH₃ / methanol / 2.5 h / 0 °C

5: 215 mg / BF₃*Et₂O / CH₂Cl₂ / 2 h / Ambient temperature

With pyridine; 18-crown-6 ether; boron trifluoride diethyl etherate; sodium methylate; In methanol; dichloromethane; acetonitrile;
DOI:10.1016/0008-6215(95)00068-5