(3R,4R,5R)-3-acetoxy-N-benzyloxycarbonyl-4-hydroxy-5-(hydroxymethyl)piperidine

Base Information

• Chemical Name: (3R,4R,5R)-3-acetoxy-N-benzyloxycarbonyl-4-hydroxy-5-(hydroxymethyl)piperidine
• CAS No.: 1333317-40-0
• Molecular Formula: C₁₆H₂₁NO₆
• Molecular Weight: 323.346

Synonyms:(3R,4R,5R)-3-acetoxy-N-benzyloxycarbonyl-4-hydroxy-5-(hydroxymethyl)piperidine

Chemical Property of (3R,4R,5R)-3-acetoxy-N-benzyloxycarbonyl-4-hydroxy-5-(hydroxymethyl)piperidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (3R,4R,5R)-3-acetoxy-N-benzyloxycarbonyl-4-hydroxy-5-(hydroxymethyl)piperidine

There total 3 articles about (3R,4R,5R)-3-acetoxy-N-benzyloxycarbonyl-4-hydroxy-5-(hydroxymethyl)piperidine 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:

acetic anhydride (108-24-7) + (3R,4R,5R)-N-benzyloxycarbonyl-3,4-dihydroxy-5-(hydroxymethyl)piperidine (568586-63-0) → (3R,4R,5R)-3-acetoxy-N-benzyloxycarbonyl-4-hydroxy-5-(hydroxymethyl)piperidine (1333317-40-0)

Guidance literature:

(3R,4R,5R)-N-benzyloxycarbonyl-3,4-dihydroxy-5-(hydroxymethyl)piperidine; With benzaldehyde dimethyl acetal; camphor-10-sulfonic acid; In chloroform; for 2h; Reflux;

acetic anhydride; With pyridine; at 20 ℃; for 2h;

DOI:10.1039/c1ob05766a

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (3R,4R,5R)-3-acetoxy-N-benzyloxycarbonyl-4-hydroxy-5-(hydroxymethyl)piperidine (1333317-40-0)

Guidance literature:

Multi-step reaction with 2 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

With benzaldehyde dimethyl acetal; camphor-10-sulfonic acid; sodium hydrogencarbonate; In tetrahydrofuran; methanol; chloroform; water;

DOI:10.1039/c1ob05766a

Reference yield:

isofagomine (169105-89-9,275363-98-9,275363-86-5,346408-06-8,275363-99-0) → (3R,4R,5R)-3-acetoxy-N-benzyloxycarbonyl-4-hydroxy-5-(hydroxymethyl)piperidine (1333317-40-0)

Guidance literature:

Multi-step reaction with 2 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

With benzaldehyde dimethyl acetal; camphor-10-sulfonic acid; sodium hydrogencarbonate; In tetrahydrofuran; methanol; chloroform; water;

DOI:10.1039/c1ob05766a

upstream raw materials:

acetic anhydride

(3R,4R,5R)-N-benzyloxycarbonyl-3,4-dihydroxy-5-(hydroxymethyl)piperidine

benzyl chloroformate

isofagomine

Downstream raw materials:

(3R,4R,5R)-3-acetoxy-5-acetyloxymethyl-N-benzyloxycarbonyl-4-[(tetra-O-acetyl-β-D-glucopyranosyl)oxy]piperidine

(3R,4R,5R)-3-acetoxy-5-acetoxymethyl-N-benzyloxycarbonyl-4-{[(tetra-O-acetyl-β-D-glucopyranosyl)-(1->4)-O-(tri-O-acetyl-β-D-glucosyl)-(1->4)-O-(tri-O-acetyl-β-D-glucosyl)]oxy}piperidine

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

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