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Synthetic method of fondaparinux sodium intermediate

A technique for fondaparinux sodium and its synthetic method, which is applied in the fields of chemical instruments and methods, preparation of sugar derivatives, sugar derivatives, etc., can solve the problems of long reaction steps and high reaction cost, and achieve reduction of production cost and simplification of synthesis route Effect

Active Publication Date: 2014-11-19
PHARMA SHANGHAI
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  • Abstract
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  • Claims
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Problems solved by technology

[0009] The synthetic method of above-mentioned technique synthetic reaction cost is high, and reaction step is longer

Method used

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  • Synthetic method of fondaparinux sodium intermediate

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Embodiment 1

[0020] The preparation process of compound 6 is:

[0021] Compound 3 (40 g, 0.13 mol) was dissolved in pyridine (240 mL, 2.98 mol), and acetic anhydride (80 ml, 0.85 mol) was added. The reaction solution was stirred at 20°C for 1-3 hours, and concentrated to obtain compound 6 (43 g, 94.5%).

[0022] The reaction equation is: .

Embodiment 2

[0024] The preparation process of compound Monomer C ring is:

[0025] Compound 6 (42.5 g, 0.12 mol) was dissolved in acetonitrile (475 mL) and water (55 ml), cerium ammonium nitrate (166 g, 0.3 mol) was added at 0°C, and the reaction solution was reacted at 20°C for 1-3 Hours, after the reaction was completed, it was filtered, extracted, washed with aqueous sodium bicarbonate solution, dried, concentrated and passed through the column to obtain compound C ring (21.5 g, 78%).

[0026] The reaction equation is: .

[0027] 1 H NMR (400 MHz, CDCl 3 ) δ 5.42 (s, 1H), 4.88 – 4.81 (m, 1H), 4.58 (d, J = 5.4 Hz, 1H), 4.11 – 4.08 (d, J = 8 Hz ,1H), 3.80 (dd, J = 7.5, 5.8 Hz, 1H), 3.60 (s, 1H), 3.45 (s, 1H), 3.04 (s, 1H), 2.10 (s, 3H).

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Abstract

The invention discloses a synthetic method of a fondaparinux sodium intermediate. The synthetic method comprises the following steps: by using a compound 3 as a raw material, performing hydroxyl acetylation to obtain a compound 6, and removing p-methoxybenzyl (PMB) of the compound 6 by using ammonium cerium nitrate to obtain a Monomer C ring. By virtue of the mode, compared with a conventional five-step method for synthesizing the Monomer C ring, the synthetic method of the fondaparinux sodium intermediate, disclosed by the invention, can be used for simplifying the synthetic route of the Monomer C ring and reducing the production cost, and is suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to the field of medicine and chemical industry, in particular to a method for synthesizing 1,6-anhydro-2-azido,3-acetyl-β-D-glucose, an important intermediate of fondaparinux sodium. Background technique [0002] Fondaparinux sodium (Fondaparinux sodium) is the world's first fully chemically synthesized pentosan compound, and the first indirect inhibitor of antithrombin-dependent factor Xa developed and produced by Sanofi Winthrop Industrie in France, CAS No. It is 114870-03-0, the Chinese name is: methyl O-(2-deoxy-6-O-sulfonic acid group-2-sulfonamido-α-D-glucopyranose)-(1→4)-O -(β-D-glucopyranose)-(1→4)-O-(2-deoxy-3,6-O-disulfonic acid-2-sulfonamido-α-D-glucopyranose )-(1→4)-O-(2-O-sulfonic acid group-α-L-pyraniduronic acid)-(1→4)-2-deoxy-6-O-sulfonic acid group- 2-Sulfonamido-α-D-glucopyranoside decasodium salt, molecular formula C 31 h 43 N 3 Na 10 o 49 S 8 , the molecular weight is 1728, and the structure is: . ...

Claims

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Application Information

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IPC IPC(8): C07H13/06C07H1/00
Inventor 王狄泳李因强
Owner PHARMA SHANGHAI
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