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
• Article Data: 12

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

Description

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 a complex organic compound that serves as an intermediate in the synthesis of Fondaparinux Sodium (F683500), a synthetic pentasaccharide. This pentasaccharide corresponds to the anti-thrombin binding site of heparin, a naturally occurring anticoagulant.

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, this compound 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.

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

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)