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Industrial Research And Consultancy Centre
Patent
A Method For Synthesis Of 6-Deoxy-L-Alloside From L-Rhamnose
Problem Statement

The commercial availability of 6-deoxy-L-sugars is limited, with only L-rhamnose and L-fucose readily accessible. The current methods for synthesizing rare sugars like 6-deoxy-L-alloside are complex, inefficient, and involve multiple protection and deprotection steps, resulting in low yields and high production costs.

Abstract

This invention presents a novel and efficient process for synthesizing 6-deoxy-L-alloside starting from L-rhamnose. The process involves a series of regioselective protections, triflation, and nucleophilic displacement reactions to transform L-rhamnose into valuable 6-deoxy-L-sugar derivatives like 6-deoxy-L-alloside.

Uniqueness of the Solution
  • Regioselective protection of hydroxyl groups in L-Rhamnose 
  • Triflation and nitrite anion-mediated inversion techniques 
  • Cascade inversions for the synthesis of 6-deoxy-L-hexoses 
  • Streamlined synthesis process for 6-deoxy-L-hexoses 
  • Utilizes inexpensive and readily available L-rhamnose 
  • Improves overall yield and efficiency compared to existing methods 
  • Cost-effective production suitable for industrial applications
Prototype Details

The prototype involves a step-by-step synthesis process starting from L-Rhamnose, employing selective protection, triflation, and inversion reactions to produce 6-deoxy-L-alloside in higher yields.

Current Status of Technology

The process has been successfully developed and demonstrated at the laboratory scale, with potential for scaling up for industrial production.

Technology readiness level

4

Societal Impact

This technology reduces production costs and increases the availability of rare sugars, leading to more affordable pharmaceuticals, and greatly impacting the biotechnology industries, thereby improving public health and contributing to economic growth.

Relevant Industries, Domains and Applications

Pharmaceutical Industry, Biotechnology Firms, Chemical Manufacturing, Agricultural Biotechnology

Applications or Domain
  • Synthesis of components for antibiotics, antitumor agents, and glycopeptides. 
  • Production of biologically active glycosides used in various therapeutic treatments. 
  • Development of new chemical pathways for sugar derivatives. 
  • Potential use in the synthesis of bioactive compounds for plant protection and growth.

Geography of IP

Type of IP

Application Number

202122003643

Filing Date
Grant Number

417359

Grant Date
Assignee(s)
Indian Institute of Technology Bombay
**This IP is owned by IIT Bombay**