(3R,4R)-4-benzoyloxy-1-benzyloxycarbonyl-3-[tri-O-acetyl-β-D-xylopyranosyl(1->3)-2,4-di-O-acetyl-β-D-xylopyranosyloxy]piperidine

Base Information

Chemical Name:(3R,4R)-4-benzoyloxy-1-benzyloxycarbonyl-3-[tri-O-acetyl-β-D-xylopyranosyl(1->3)-2,4-di-O-acetyl-β-D-xylopyranosyloxy]piperidine
CAS No.:1363568-04-0
Molecular Formula:C₄₀H₄₇NO₁₈
Molecular Weight:829.809
Hs Code.:

Synonyms:(3R,4R)-4-benzoyloxy-1-benzyloxycarbonyl-3-[tri-O-acetyl-β-D-xylopyranosyl(1->3)-2,4-di-O-acetyl-β-D-xylopyranosyloxy]piperidine

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Chemical Property of (3R,4R)-4-benzoyloxy-1-benzyloxycarbonyl-3-[tri-O-acetyl-β-D-xylopyranosyl(1->3)-2,4-di-O-acetyl-β-D-xylopyranosyloxy]piperidine

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Technology Process of (3R,4R)-4-benzoyloxy-1-benzyloxycarbonyl-3-[tri-O-acetyl-β-D-xylopyranosyl(1->3)-2,4-di-O-acetyl-β-D-xylopyranosyloxy]piperidine

There total 4 articles about (3R,4R)-4-benzoyloxy-1-benzyloxycarbonyl-3-[tri-O-acetyl-β-D-xylopyranosyl(1->3)-2,4-di-O-acetyl-β-D-xylopyranosyloxy]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: 75.0%

: tri-O-acetyl-β-D-xylopyranosyl(1->3)-2,4-di-O-acetyl-D-xylosyl trichloroacetimidate

: 266688-43-1
2-O-benzyl-N-benzyloxycarbonyl-1,4,5-trideoxy-1,5-imino-D-threo-pentitol

: 1363568-04-0
(3R,4R)-4-benzoyloxy-1-benzyloxycarbonyl-3-[tri-O-acetyl-β-D-xylopyranosyl(1->3)-2,4-di-O-acetyl-β-D-xylopyranosyloxy]piperidine

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at -40 - 0 ℃; for 1h; Molecular sieve; Inert atmosphere;
DOI:10.1021/ja211836t

Reference yield:

: 19186-36-8,71166-82-0,77824-39-6,71143-90-3
acetyl 2,4-di-O-acetyl-β-D-xylopyranoside

: 1363568-04-0
(3R,4R)-4-benzoyloxy-1-benzyloxycarbonyl-3-[tri-O-acetyl-β-D-xylopyranosyl(1->3)-2,4-di-O-acetyl-β-D-xylopyranosyloxy]piperidine

Guidance literature:: Multi-step reaction with 5 steps

1.1: pyridine / dichloromethane

2.1: hydrogen bromide; acetic acid

3.1: 2,6-dimethylpyridine; calcium sulfate; silver (II) carbonate / acetonitrile / 0.17 h / 20 °C / Inert atmosphere; Darkness

3.2: 12 h / 20 °C / Inert atmosphere; Darkness

3.3: 5 h / 20 °C

4.1: hydrazinium monoacetate / N,N-dimethyl-formamide / 1.5 h / 20 °C

4.2: 3 h / 20 °C

5.1: boron trifluoride diethyl etherate / dichloromethane / 1 h / -40 - 0 °C / Molecular sieve; Inert atmosphere

With pyridine; 2,6-dimethylpyridine; calcium sulfate; silver (II) carbonate; boron trifluoride diethyl etherate; hydrogen bromide; hydrazinium monoacetate; acetic acid; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja211836t

Reference yield:

: 82977-18-2,82977-19-3
1,2,4-tri-O-acetyl-3-O-chloroacetyl-β-D-xylopyranose

: 1363568-04-0
(3R,4R)-4-benzoyloxy-1-benzyloxycarbonyl-3-[tri-O-acetyl-β-D-xylopyranosyl(1->3)-2,4-di-O-acetyl-β-D-xylopyranosyloxy]piperidine

Guidance literature:: Multi-step reaction with 4 steps

1.1: hydrogen bromide; acetic acid

2.1: 2,6-dimethylpyridine; calcium sulfate; silver (II) carbonate / acetonitrile / 0.17 h / 20 °C / Inert atmosphere; Darkness

2.2: 12 h / 20 °C / Inert atmosphere; Darkness

2.3: 5 h / 20 °C

3.1: hydrazinium monoacetate / N,N-dimethyl-formamide / 1.5 h / 20 °C

3.2: 3 h / 20 °C

4.1: boron trifluoride diethyl etherate / dichloromethane / 1 h / -40 - 0 °C / Molecular sieve; Inert atmosphere

With 2,6-dimethylpyridine; calcium sulfate; silver (II) carbonate; boron trifluoride diethyl etherate; hydrogen bromide; hydrazinium monoacetate; acetic acid; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja211836t