245432-69-3

Basic information

• Product Name: 1,2,3-tri-O-acetyl-3-C-(benzyloxymethyl)-α/β-D-erythrofuranoside
• Synonyms: 1,2,3-tri-O-acetyl-3-C-(benzyloxymethyl)-α/β-D-erythrofuranoside
• CAS NO: 245432-69-3
• Molecular Weight: 366.368
• Mol File: 245432-69-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1,2,3-tri-O-acetyl-3-C-(benzyloxymethyl)-α/β-D-erythrofuranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3-tri-O-acetyl-3-C-(benzyloxymethyl)-α/β-D-erythrofuranoside(245432-69-3)
• EPA Substance Registry System: 1,2,3-tri-O-acetyl-3-C-(benzyloxymethyl)-α/β-D-erythrofuranoside(245432-69-3)

Safety Data

• Hazardous Substances Data: 245432-69-3(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 70147-50-1 2,3-O-isopropylidene-D-erythro-apiofuranoside 
• 102804-16-0 (R)-1-((S)-5,5-Bis-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethane-1,2-diol 
• 102850-83-9 2-C-(hydroxymethyl)-2,3:4,5-di-O-isopropylidene-D-threo-pentitol 
• 70147-50-1 3-C-hydroxymethyl-2,3-O-isopropylidene-β-D-erythrofuranoside 
• 25904-06-7 1,2:3,5-di-O-isopropylidene-α-D-threo-apiofuranose 
• 24679-88-7 methyl 2,3-O-isopropylidene-3-C-(hydroxymethyl)-α-D-erythrofuranoside 

Downstream Products

• 1610460-11-1 C₁₉H₂₄N₃O₈P 
• 1610459-86-3 1'-(thymin-1-yl)-2',3'-(dideoxydidehydro)-5'-(O-benzyl)-β-D-apio-D-furanose 
• 1610459-85-2 1'-(adenin-9-yl)-2',3'-(O-thiocarbonyl)-5'-(O-benzyl)-β-D-apio-D-furanose 
• 1610459-84-1 1'-(thymin-1-yl)-2',3'-(O-thiocarbonyl)-5'-(O-benzyl)-β-D-apio-D-furanose 
• 1610459-83-0 1'-(adenin-9-yl)-5'-O-benzyl-β-D-apio-D-furanose 
• 1610459-82-9 1'-(thymin-1-yl)-5'-O-benzyl-β-D-apio-D-furanose 
• 28440-12-2 1'-(adenin-9-yl)-β-D-apio-D-furanose 
• 1610460-03-1 1'-(thymin-1-yl)-2',3'-dideoxy-β-D-apio-D-furanose [phenyl-(isopropoxy-L-alaninyl)]phosphate 
• 1610460-01-9 1'-(thymin-1-yl)-2',3'-dideoxy-β-D-apio-D-furanose [phenyl-(benzoxy-L-alaninyl)]phosphate 
• 801320-28-5 methyl (2,3-di-O-acetyl-3-C-(benzyloxymethyl)β-D-erythrofuranosyl)-(1->2)-6-O-(tert-butyldiphenyl)silyl-3,4-O-isopropylidene-α-D-galactopyranoside 
• 801320-31-0 methyl (2,3-di-O-acetyl-3-C-(benzyloxymethyl)-β-D-erythrofuranosyl)-(1->2) (methyl 3,4-O-isopropylidene-α-D-galactopyranosid)uronate 
• 801320-29-6 methyl (2,3-di-O-acetyl-3-C-(benzyloxymethyl)-β-D-erythrofuranosyl)-(1->2)-3,4-O-isopropylidene-α-D-galactopyranoside 
• 209113-74-6 3,4,5-trimethoxyphenyl 2,3,4-tri-O-phenoxyacetyl-6-O-(2,3-di-O-phenoxyacetyl-β-D-erythro-apiofuranosyl)-β-D-glucopyranoside 

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.

An expeditious route to the synthesis of kelampayosides A and B

Chemoselective NIS/cat. TfOH-mediated glycosylation of ethyl 2,3,4-tri- O-benzoyl-1-thio-β-D-glucopyranoside (13) with ethyl 2,3-di-O-acetyl-5-O- benzyl-1-thio-α/β-erythro-apiofuranoside (4a) gave direct 14 in an excellent yield. BF3·Et2O-catalysed condensation of the α- trichloroacetimidate 31, accessible in two steps from 14, with 3,4,5- trimethoxyphenol gave β-linked derivative 32 followed by deprotection gave Kelampayoside A. Protecting group manipulations of 32 and subsequent caffeoylation of resulting 36 followed by deprotection gave Kelampayoside B.