114903-05-8

Basic information

• Product Name: a-D-Glucopyranoside, Methyl O-2-azido-2-deoxy-3,4-bis-O-(phenylMethyl)-a-D-glucopyranosyl-(14) -O-2,3-bis-O-(phenylMethyl)-b-D-glucopyranuronosyl-(14)-O-2-azido- 2-deoxy-a-D-glucopyranosyl-(14)-O-3-O-(phenylMethyl)-a-L-idopyranu ronosyl-(14)-2-deoxy-2
• Synonyms: a-D-Glucopyranoside, Methyl O-2-azido-2-deoxy-3,4-bis-O-(phenylMethyl)-a-D-glucopyranosyl-(14) -O-2,3-bis-O-(phenylMethyl)-b-D-glucopyranuronosyl-(14)-O-2-azido- 2-deoxy-a-D-glucopyranosyl-(14)-O-3-O-(phenylMethyl)-a-L-idopyranu ronosyl-(14)-2-deoxy-2;4)-2-deoxy-2-[[(phenylmethoxy)carbonyl]amino]-3-O-(phenylmethyl)-alpha-D-glucopyranoside;4)-O-2,3-bis-O-(phenylmethyl)-beta-D-glucopyranuronosyl-(1→4)-O-2-azido-2-deoxy-alpha-D-glucopyranosyl-(1→4)-O-3-O-(phenylmethyl)-alpha-L-idopyranuronosyl-(1→Methyl O-2-azido-2-deoxy-3,4-bis-O-(phenylmethyl)-alpha-D-glucopyranosyl-(1→Pentasaccharide N-3 Intermediate;Fondaparinux interMediate N-3
• CAS NO: 114903-05-8
• Molecular Formula: C81H91N7O27
• Molecular Weight: 1594.62
• EINECS: 1533716-785-6
• Mol File: 114903-05-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: a-D-Glucopyranoside, Methyl O-2-azido-2-deoxy-3,4-bis-O-(phenylMethyl)-a-D-glucopyranosyl-(14) -O-2,3-bis-O-(phenylMethyl)-b-D-glucopyranuronosyl-(14)-O-2-azido- 2-deoxy-a-D-glucopyranosyl-(14)-O-3-O-(phenylMethyl)-a-L-idopyranu ronosyl-(14)-2-deoxy-2(CAS DataBase Reference)
• NIST Chemistry Reference: a-D-Glucopyranoside, Methyl O-2-azido-2-deoxy-3,4-bis-O-(phenylMethyl)-a-D-glucopyranosyl-(14) -O-2,3-bis-O-(phenylMethyl)-b-D-glucopyranuronosyl-(14)-O-2-azido- 2-deoxy-a-D-glucopyranosyl-(14)-O-3-O-(phenylMethyl)-a-L-idopyranu ronosyl-(14)-2-deoxy-2(114903-05-8)
• EPA Substance Registry System: a-D-Glucopyranoside, Methyl O-2-azido-2-deoxy-3,4-bis-O-(phenylMethyl)-a-D-glucopyranosyl-(14) -O-2,3-bis-O-(phenylMethyl)-b-D-glucopyranuronosyl-(14)-O-2-azido- 2-deoxy-a-D-glucopyranosyl-(14)-O-3-O-(phenylMethyl)-a-L-idopyranu ronosyl-(14)-2-deoxy-2(114903-05-8)

Safety Data

• Hazardous Substances Data: 114903-05-8(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Industry:
a-D-Glucopyranoside, Methyl O-2-azido-2-deoxy-3,4-bis-O-(phenylMethyl)-a-D-glucopyranosyl-(14) -O-2,3-bis-O-(phenylMethyl)-b-D-glucopyranuronosyl-(14)-O-2-azido2-deoxy-a-D-glucopyranosyl-(14)-O-3-O-(phenylMethyl)-a-L-idopyranu ronosyl-(14)-2-deoxy-2 is used as an intermediate in the synthesis of Fondaparinux Sodium for its anti-thrombotic properties. a-D-Glucopyranoside, Methyl O-2-azido-2-deoxy-3,4-bis-O-(phenylMethyl)-a-D-glucopyranosyl-(14) -O-2,3-bis-O-(phenylMethyl)-b-D-glucopyranuronosyl-(14)-O-2-azido2-deoxy-a-D-glucopyranosyl-(14)-O-3-O-(phenylMethyl)-a-L-idopyranu ronosyl-(14)-2-deoxy-2 plays a crucial role in the development of medications aimed at preventing blood clot formation, which is essential in treating and managing various cardiovascular conditions.
2. Used in Research and Development:
In addition to its application in the pharmaceutical industry, a-D-Glucopyranoside, Methyl O-2-azido-2-deoxy-3,4-bis-O-(phenylMethyl)-a-D-glucopyranosyl-(14) -O-2,3-bis-O-(phenylMethyl)-b-D-glucopyranuronosyl-(14)-O-2-azido- 2-deoxy-a-D-glucopyranosyl-(14)-O-3-O-(phenylMethyl)-a-L-idopyranu ronosyl-(14)-2-deoxy-2 may also be utilized in research and development settings. It can be employed to study the structure-activity relationships of heparin and its derivatives, as well as to develop new anticoagulant drugs with improved properties, such as better bioavailability, longer half-life, or reduced side effects.

Relevant articles and documents

Formal Synthesis of Anticoagulant Drug Fondaparinux Sodium

The practical formal synthesis of the anticoagulant drug fondaparinux sodium 1 was accomplished using an optimized modular synthetic strategy. The important pentasaccharide 2, a precursor for the synthesis of fondaparinux sodium, was synthesized on a 10 g scale in 14 collective steps with 3.5% overall yield from well-functionalized monosaccharide building blocks. The strategy involved a convergent [3 + 2] coupling approach, with excellent stereoselectivity in every step of glycosylation from the monosaccharide building blocks. Efficient routes to the syntheses of these fully functionalized building blocks were developed, minimizing oligosaccharide stage functional-group modifications. The syntheses of all building blocks avoided rigorous reaction conditions and the use of expensive reagents. In addition, common intermediates and a series of one-pot reactions were employed to enhance synthetic efficiency, improving the yield considerably. In the monosaccharide-to-oligosaccharide assembly reactions, cheaper activators (e.g., NIS/TfOH, TESOTf, and TfOH) were used to facilitate highly efficient glycosylations. Furthermore, crystallization of several monosaccharide and oligosaccharide intermediates significantly simplified purification procedures, which would be greatly beneficial to the scalable synthesis of fondaparinux sodium.

A pentose compound of intermediate and its preparation method

The invention relates to an intermediate of a pentose compound and a preparation method of the intermediate, and particularly relates to intermediates IA and IB of fondaparinux sodium and a preparation method thereof. According to the intermediate and the preparation method disclosed by the invention, substituted benzoyl is taken as a hydroxyl protective group for the intermediate IA, and the IA is used for preparing the intermediate IB of the fondaparinux sodium, wherein the operation is simple, and the productive rate and the yield are both high; moreover, the intermediate is easy to cure and pure in each reaction step, so the intermediate is more suitable for industrial production; meanwhile, the invention also relates to application of the intermediate IB in preparation of the fondaparinux sodium. The intermediates IA and IB are as shown in the specification.

New process method for preparing fondaparinux sodium

The invention discloses a new process method for preparing fondaparinux sodium. A fondaparinux sodium crude product is prepared from total protective pentose through ester hydrolysis reaction, methylesterification, hydrogenation, sulfonated reaction and t

the sulphur reaches the liver last of the ten Heavenly Stems sodium and intermediate thereof, and preparation method

The invention relates to fondaparinux sodium, intermediates thereof and preparation methods in the technical field of chemical preparation, particularly relates to the preparation methods of the fondaparinux sodium and the intermediates of the fondaparinux sodium, comprising the fondaparinux sodium, a disaccharide intermediate of the fondaparinux sodium, a tetrasccharide intermediate of the fondaparinux sodium, a pentasaccharide intermediate of the fondaparinux sodium and the corresponding preparation methods. The structure of the fondaparinux sodium is shown as the chemical compound (1). The invention also relates to the disaccharide intermediate, the tetrasccharide intermediate and the pentasaccharide intermediate which are used for preparing the fondaparinux sodium. The invention designs a novel synthetic route to prepare the fondaparinux sodium. The novel synthetic route has mild reactions, good reaction selectivity, strong controllability and low operation difficulty, and is prone to achievement of industrial production.

PROCESS FOR THE PRODUCTION OF FONDAPARINUX SODIUM

The present invention refers to a fly step compounds of formula ABC5 novel sodium [...] provides manufacturing method: In some embodiments, step for the synthesis intermediates are sodium [...] fly is provided in addition. (by machine translation)

PROCESS FOR THE PRODUCTION OF FONDAPARINUX SODIUM

The present invention provides novel processes for the preparation of Fondaparinux sodium by using the compound of formula ABC5 In some embodiments, the intermediates for the synthesis of Fondaparinux sodium, are also provided.

PROCESS FOR THE PRODUCTION OF FONDAPARINUX SODIUM

The present invention provides improved processes of preparing Fondaparinux sodium comprising converting a compound of formula ABCDE4 to Fondaparinux sodium at a reaction pH of no more than about 9.0. In some embodiments, the intermediates for the synthes

PROCESS FOR THE PRODUCTION OF FONDAPARINUX SODIUM

The present invention provides novel processes for the preparation of Fondaparinux sodium by using the compound of formula ABC5. In some embodiments, the intermediates for the synthesis of Fondaparinux sodium, are also provided.

PROCESS FOR THE PRODUCTION OF FONDAPARINUX SODIUM

The present invention provides improved processes of preparing Fondaparinux sodium comprising converting a compound of formula ABCDE4 to Fondaparinux sodium at a reaction pH of no more than about 9.0. In some embodiments, the intermediates for the synthes

PROCESS FOR PREPARING HEPARINOIDS AND INTERMEDIATES USEFUL IN THE SYNTHESIS THEREOF

Processes are disclosed for the synthesis of the Factor Xa anticoagulant fondaparinux and related compounds. Protected pentasaccharide intermediates and efficient and scalable processes for the industrial scale production of fondaparinux sodium by conversion of the protected pentasaccharide intermediates via a sequence of deprotection and sulfonation reactions are provided.