1189361-01-0

Basic information

• Product Name: 2,6-anhydro-3-azido-1,4-di-O-benzyl-3,5-dideoxy-D-arabino-hex-5-enitol
• Synonyms: 2,6-anhydro-3-azido-1,4-di-O-benzyl-3,5-dideoxy-D-arabino-hex-5-enitol
• CAS NO: 1189361-01-0
• Molecular Weight: 351.405
• Mol File: 1189361-01-0.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2,6-anhydro-3-azido-1,4-di-O-benzyl-3,5-dideoxy-D-arabino-hex-5-enitol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-anhydro-3-azido-1,4-di-O-benzyl-3,5-dideoxy-D-arabino-hex-5-enitol(1189361-01-0)
• EPA Substance Registry System: 2,6-anhydro-3-azido-1,4-di-O-benzyl-3,5-dideoxy-D-arabino-hex-5-enitol(1189361-01-0)

Safety Data

• Hazardous Substances Data: 1189361-01-0(Hazardous Substances Data)

Upstream product

• 98-88-4 benzoyl chloride 
• 81562-22-3 1,5-anhydro-3,6-di-O-benzoyl-2-deoxy-4-O-mesyl-D-arabino-hex-1-enitol 
• 13265-84-4 D-glucal 
• 100-39-0 benzyl bromide 
• 475630-50-3 4-azido-4-deoxy-3,6-di-O-benzoyl-D-galactal 

Downstream Products

• 1189361-02-1 O-acetyl 2-O-acetyl-4-azido-4-deoxy-3,6-di-O-benzyl-β-D-galactopyranoside 
• 1235983-90-0 2,6-anhydro-3-azido-1,4-di-O-benzyl-3,5-dideoxy-5-C-formyl-D-arabino-hex-5-enitol 
• 1189361-42-9 O-trichloroacetimidoyl {[2,3,4-tri-O-benzyl-β-D-xylopyranosyl-(1->4)]-2,3-di-O-isopropylidene-L-rhamnopyranosyl-(1->2)}-4-azido-4-deoxy-3,6-di-O-benzyl-α-D-galactopyranoside 
• 1392506-69-2 O-triisopropylsilyl {[2,3,4-tri-O-benzyl-β-D-xylopyranosyl-(1->4)]-2,3-di-O-isopropylidene-L-rhamnopyranosyl-(1->2)}-4-azido-4-deoxy-3,6-di-O-benzyl-β-D-galactopyranoside 
• 1189361-04-3 O-triisopropylsilyl 4-azido-4-deoxy-3,6-di-O-benzyl-β-D-galactopyranoside 

Relevant articles and documents

TRITERPENE SAPONIN ANALOGUES

The present application relates to triterpene glycoside saponin-derived adjuvants, syntheses thereof, and intermediates thereto. The application also provides pharmaceutical compositions comprising compounds of the present invention and methods of using said compounds or compositions in the treatment of and immunization for infectious diseases.

Design and synthesis of potent Quillaja saponin vaccine adjuvants

The success of antitumor and antiviral vaccines often requires the use of an adjuvant, a substance that significantly enhances the immune response to a coadministered antigen. Only a handful of adjuvants have both sufficient potency and acceptable toxicity for clinical investigation. One promising adjuvant is QS-21, a saponin natural product that is the immunopotentiator of choice in many cancer and infectious disease vaccine clinical trials. However, the therapeutic promise of QS-21 adjuvant is curtailed by several factors, including its scarcity, difficulty in purification to homogeneity, dose-limiting toxicity, and chemical instability. Here, we report the design, synthesis, and evaluation of chemically stable synthetic saponins. These novel, amide-modified, non-natural substances exhibit immunopotentiating effects in vivo that rival or exceed that of QS-21 in evaluations with the GD3-KLH melanoma conjugate vaccine. The highly convergent synthetic preparation of these novel saponins establishes new avenues for discovering improved molecular adjuvants for specifically tailored vaccine therapies.

TRITERPENE SAPONINS, METHODS OF SYNTHESIS, AND USES THEREOF

The present invention relates to triterpene glycoside saponin-derived adjuvants, syntheses thereof, intermediates thereto, and uses thereof. QS-7 is a potent immuno-adjuvant that is significantly less toxic than QS-21, a related saponin that is currently the favored adjuvant in anticancer and antiviral vaccines. Tedious isolation and purification protocols have hindered the clinical development of QS-7. A novel semi-synthetic method is provided wherein a hydrolyzed prosapogenin mixture is used to synthesize QS-7, QS-21, and related analogs, greatly facilitating access to QS-7 and QS-21 analogs for preclinical and clinical evaluation.