850004-55-6

Basic information

• Product Name: (3R,4S,5R)-2-Allyloxy-3,5-bis-benzyloxy-tetrahydro-pyran-4-ol
• Synonyms: (3R,4S,5R)-2-Allyloxy-3,5-bis-benzyloxy-tetrahydro-pyran-4-ol
• CAS NO: 850004-55-6
• Molecular Weight: 370.445
• Mol File: 850004-55-6.mol

Chemical Properties

• CAS DataBase Reference: (3R,4S,5R)-2-Allyloxy-3,5-bis-benzyloxy-tetrahydro-pyran-4-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4S,5R)-2-Allyloxy-3,5-bis-benzyloxy-tetrahydro-pyran-4-ol(850004-55-6)
• EPA Substance Registry System: (3R,4S,5R)-2-Allyloxy-3,5-bis-benzyloxy-tetrahydro-pyran-4-ol(850004-55-6)

Safety Data

• Hazardous Substances Data: 850004-55-6(Hazardous Substances Data)

Upstream product

• 87-72-9 D-Xylose 
• 100-44-7 benzyl chloride 
• 182212-10-8 1-O-allyl-D-xylopyranoside 

Downstream Products

• 1072450-37-3 trichloroacetimidoyl 2,3,4-tri-O-benzyl-β-D-xylopyranosyl-(1->3)-2,4-di-O-benzyl-β-D-xylopyranosyl-(1->4)-2,3-di-O-isopropylidene-α-L-rhamnopyranoside 
• 1072450-36-2 triisopropylsilyl 2,3,4-tri-O-benzyl-β-D-xylopyranosyl-(1->3)-2,4-di-O-benzyl-β-D-xylopyranosyl-(1->4)-2,3-di-O-isopropylidene-α-L-rhamnopyranoside 
• 1026022-17-2 O-triisopropylsilyl {[5-O-benzyl-2,3-di-O-benzylidene-β-D-apiofuranosyl-(1->3)]-2,4-di-O-benzyl-β-D-xylopyranosyl-(1->4)}-2,3-di-O-isopropylidene-α-L-rhamnopyranoside 
• 1026022-16-1 O-triisopropylsilyl {[2,3-di-O-acetyl-5-O-benzyl-β-D-apiofuranosyl-(1->3)]-2,4-di-O-benzyl-β-D-xylopyranosyl-(1->4)}-2,3-di-O-isopropylidene-α-L-rhamnopyranoside 
• 1026022-15-0 O-triisopropylsilyl [2,4-di-O-benzyl-β-D-xylopyranosyl-(1->4)]-2,3-di-O-isopropylidene-α-L-rhamnopyranoside 
• 912805-54-0 C₆₄H₈₅NO₂₀Si 
• 912805-52-8 7-{3,5-bis-benzyloxy-4-[6a-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yloxy]-tetrahydro-pyran-2-yloxy}-2,2,6-trimethyl-4-triisopropylsilanyloxy-tetrahydro-[1,3]dioxolo[4,5-c]pyran 
• 850004-34-1 O-triisopropylsilyl [2,3-di-O-acetyl-5-O-benzyl-β-D-apiofuranosyl-(1->3)]-O-[2,4-di-O-benzyl-β-D-xylopyranosyl-(1->4)]-O-2,3-O-isopropylidene-β-L-rhamnopyranoside 
• 850004-33-0 O-triisopropylsilyl-O-[2,4-di-O-benzyl-3-hydroxy-β-D-xylopyranosyl-(1->4)]-O-2,3-O-isopropylidene-β-L-rhamnopyranoside 

Relevant articles and documents

TRITERPENE SAPONIN SYNTHESIS, INTERMEDIATES AND ADJUVANT COMBINATIONS

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.

Synthetic studies of complex immunostimulants from Quillaja saponaria: Synthesis of the potent clinical immunoadjuvant QS-21Aapi

QS-21 is one of the most promising new adjuvants for immune response potentiation and dose-sparing in vaccine therapy given its exceedingly high level of potency and its favorable toxicity profile. Melanoma, breast cancer, small cell lung cancer, prostate cancer, HIV-1, and malaria are among the numerous maladies targeted in more than 80 recent and ongoing vaccine therapy clinical trials involving QS-21 as a critical adjuvant component for immune response augmentation. QS-21 is a natural product immunostimulatory adjuvant, eliciting both T-cell- and antibody-mediated immune responses with microgram doses. Herein is reported the synthesis of QS-21 Aapi in a highly modular strategy, applying novel glycosylation methodologies to a convergent construction of the potent saponin immunostimulant. The chemical synthesis of QS-21 offers unique opportunities to probe its mode of biological action through the preparation of otherwise unattainable nonnatural saponin analogues.