Benzoic acid (3S,4R)-2-oxo-4-((2S,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-piperidin-3-yl ester

Base Information

• Chemical Name: Benzoic acid (3S,4R)-2-oxo-4-((2S,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-piperidin-3-yl ester
• CAS No.: 284045-99-4
• Molecular Formula: C₂₃H₂₇NO₁₁
• Molecular Weight: 493.467

Synonyms:Benzoic acid (3S,4R)-2-oxo-4-((2S,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-piperidin-3-yl ester

Chemical Property of Benzoic acid (3S,4R)-2-oxo-4-((2S,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-piperidin-3-yl ester

Chemical Property:

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Technology Process of Benzoic acid (3S,4R)-2-oxo-4-((2S,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-piperidin-3-yl ester

There total 3 articles about Benzoic acid (3S,4R)-2-oxo-4-((2S,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-piperidin-3-yl 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: 71.0%

2,3,4-tri-O-acetyl-α-D-xylopyranosyl trichloroacetimidate (128376-91-0,869848-87-3) + Benzoic acid (3S,4R)-4-hydroxy-2-oxo-piperidin-3-yl ester → Benzoic acid (3S,4R)-2-oxo-4-((2S,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-piperidin-3-yl ester (284045-99-4)

Guidance literature:

With boron trifluoride diethyl etherate; In 1,2-dichloro-ethane; at 20 ℃; for 2h;

DOI:10.1021/ja0002870

Reference yield:

benzoyl chloride (98-88-4) → Benzoic acid (3S,4R)-2-oxo-4-((2S,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-piperidin-3-yl ester (284045-99-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / pyridine / -40 - 20 °C

2: 71 percent / BF₃*Et₂O / 1,2-dichloro-ethane / 2 h / 20 °C

With pyridine; boron trifluoride diethyl etherate; In 1,2-dichloro-ethane; 1: benzoylation / 2: glycosylation;

DOI:10.1021/ja0002870

Reference yield:

5-amino-4,5-dideoxy-D-threo-pentono-1,5-lactam (266688-40-8) → Benzoic acid (3S,4R)-2-oxo-4-((2S,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-pyran-2-yloxy)-piperidin-3-yl ester (284045-99-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / pyridine / -40 - 20 °C

2: 71 percent / BF₃*Et₂O / 1,2-dichloro-ethane / 2 h / 20 °C

With pyridine; boron trifluoride diethyl etherate; In 1,2-dichloro-ethane; 1: benzoylation / 2: glycosylation;

DOI:10.1021/ja0002870

upstream raw materials:

2,3,4-tri-O-acetyl-α-D-xylopyranosyl trichloroacetimidate

benzoyl chloride

5-amino-4,5-dideoxy-D-threo-pentono-1,5-lactam

Downstream raw materials:

(3S,4R)-3-Hydroxy-4-((2S,3R,4S,5R)-3,4,5-trihydroxy-tetrahydro-pyran-2-yloxy)-piperidin-2-one

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