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

Base Information

• Chemical Name: (3R,4R,5R)-3-acetoxy-5-acetyloxymethyl-N-benzyloxycarbonyl-4-{[(tetra-O-acetyl-β-D-glucopyranosyl)-(1->4)-O-(tri-O-acetyl-β-D-glucosyl)]oxy}piperidine
• CAS No.: 568586-68-5
• Molecular Formula: C₄₄H₅₇NO₂₄
• Molecular Weight: 983.929

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

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

Chemical Property:

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

There total 5 articles about (3R,4R,5R)-3-acetoxy-5-acetyloxymethyl-N-benzyloxycarbonyl-4-{[(tetra-O-acetyl-β-D-glucopyranosyl)-(1->4)-O-(tri-O-acetyl-β-D-glucosyl)]oxy}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: 61.0%

(3R,4R,5R)-3-acetoxy-5-acetyloxymethyl-N-benzyloxycarbonyl-4-hydroxypiperidine (1333317-41-1) + 4-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl trichloracetimidate (92052-38-5,106256-81-9,106256-89-7,126736-02-5,132287-70-8,132287-71-9,139403-73-9,130703-21-8) → (3R,4R,5R)-3-acetoxy-5-acetyloxymethyl-N-benzyloxycarbonyl-4-{[(tetra-O-acetyl-β-D-glucopyranosyl)-(1->4)-O-(tri-O-acetyl-β-D-glucosyl)]oxy}piperidine (568586-68-5)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -30 - 20 ℃; for 2h; Molecular sieve;

DOI:10.1039/c1ob05766a

Reference yield: 27.0%

acetic anhydride (108-24-7) + 1-deoxy-1-fluoro-α-D-glucose (2106-10-7) + (3R,4R,5R)-N-benzyloxycarbonyl-3,4-dihydroxy-5-(hydroxymethyl)piperidine (568586-63-0) → (3R,4R,5R)-3-acetoxy-5-acetyloxymethyl-N-benzyloxycarbonyl-4-[(tetra-O-acetyl-β-D-glucopyranosyl)oxy]piperidine (568586-67-4) + (3R,4R,5R)-3-acetoxy-5-acetyloxymethyl-N-benzyloxycarbonyl-4-{[(tetra-O-acetyl-β-D-glucopyranosyl)-(1->4)-O-(tri-O-acetyl-β-D-glucosyl)]oxy}piperidine (568586-68-5) + (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 (568586-70-9)

Guidance literature:

1-deoxy-1-fluoro-α-D-glucose; (3R,4R,5R)-N-benzyloxycarbonyl-3,4-dihydroxy-5-(hydroxymethyl)piperidine; With AbgGlu₃₅₈Ser; sodium hydrogencarbonate; at 20 ℃; for 168h; pH=7.9;

acetic anhydride; With pyridine;

DOI:10.1071/CH02165

Reference yield:

isofagomine (169105-89-9,275363-98-9,275363-86-5,346408-06-8,275363-99-0) → (3R,4R,5R)-3-acetoxy-5-acetyloxymethyl-N-benzyloxycarbonyl-4-{[(tetra-O-acetyl-β-D-glucopyranosyl)-(1->4)-O-(tri-O-acetyl-β-D-glucosyl)]oxy}piperidine (568586-68-5)

Guidance literature:

Multi-step reaction with 4 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

4.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / -30 - 20 °C / Molecular sieve

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

DOI:10.1039/c1ob05766a

upstream raw materials:

acetic anhydride

1-deoxy-1-fluoro-α-D-glucose

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

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

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