(3R,4R,5R)-3-acetoxy-5-acetyloxymethyl-N-benzyloxycarbonyl-4-hydroxypiperidine

Base Information

Chemical Name:(3R,4R,5R)-3-acetoxy-5-acetyloxymethyl-N-benzyloxycarbonyl-4-hydroxypiperidine
CAS No.:1333317-41-1
Molecular Formula:C₁₈H₂₃NO₇
Molecular Weight:365.383
Hs Code.:

Synonyms:(3R,4R,5R)-3-acetoxy-5-acetyloxymethyl-N-benzyloxycarbonyl-4-hydroxypiperidine

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Chemical Property of (3R,4R,5R)-3-acetoxy-5-acetyloxymethyl-N-benzyloxycarbonyl-4-hydroxypiperidine

Chemical Property:

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Technology Process of (3R,4R,5R)-3-acetoxy-5-acetyloxymethyl-N-benzyloxycarbonyl-4-hydroxypiperidine

There total 4 articles about (3R,4R,5R)-3-acetoxy-5-acetyloxymethyl-N-benzyloxycarbonyl-4-hydroxypiperidine 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: 83.0%

: 1333317-40-0
(3R,4R,5R)-3-acetoxy-N-benzyloxycarbonyl-4-hydroxy-5-(hydroxymethyl)piperidine

: 75-36-5
acetyl chloride

: 1333317-41-1
(3R,4R,5R)-3-acetoxy-5-acetyloxymethyl-N-benzyloxycarbonyl-4-hydroxypiperidine

Guidance literature:: With pyridine; In dichloromethane; at -30 - 20 ℃; for 3h;
DOI:10.1039/c1ob05766a

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 1333317-41-1
(3R,4R,5R)-3-acetoxy-5-acetyloxymethyl-N-benzyloxycarbonyl-4-hydroxypiperidine

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium hydrogencarbonate / tetrahydrofuran; methanol; water / 1 h / 20 °C

2.1: benzaldehyde dimethyl acetal; camphor-10-sulfonic acid / chloroform / 2 h / Reflux

2.2: 2 h / 20 °C

3.1: pyridine / dichloromethane / 3 h / -30 - 20 °C

With pyridine; benzaldehyde dimethyl acetal; camphor-10-sulfonic acid; sodium hydrogencarbonate; In tetrahydrofuran; methanol; dichloromethane; chloroform; water;
DOI:10.1039/c1ob05766a

Reference yield:

: 568586-63-0
(3R,4R,5R)-N-benzyloxycarbonyl-3,4-dihydroxy-5-(hydroxymethyl)piperidine

: 1333317-41-1
(3R,4R,5R)-3-acetoxy-5-acetyloxymethyl-N-benzyloxycarbonyl-4-hydroxypiperidine

Guidance literature:: Multi-step reaction with 2 steps

1.1: benzaldehyde dimethyl acetal; camphor-10-sulfonic acid / chloroform / 2 h / Reflux

1.2: 2 h / 20 °C

2.1: pyridine / dichloromethane / 3 h / -30 - 20 °C

With pyridine; benzaldehyde dimethyl acetal; camphor-10-sulfonic acid; In dichloromethane; chloroform;
DOI:10.1039/c1ob05766a