19186-37-9

Basic information

• Product Name: Acetyl 2-O,3-O,4-O-triacetyl-α-D-arabinopyranoside
• Synonyms: Acetyl 2-O,3-O,4-O-triacetyl-α-D-arabinopyranoside;α-D-Arabinopyranose tetraacetate;alpha-D-Arabinopyranose tetraacetate
• CAS NO: 19186-37-9
• Molecular Formula: C₁₃H₁₈O₉
• Molecular Weight: 318.27662
• Mol File: 19186-37-9.mol
• Article Data: 84

Chemical Properties

• Melting Point: 93-95 °C
• Boiling Point: 362.9±42.0 °C(Predicted)
• Appearance: /
• Density: 1.29±0.1 g/cm3(Predicted)
• CAS DataBase Reference: Acetyl 2-O,3-O,4-O-triacetyl-α-D-arabinopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Acetyl 2-O,3-O,4-O-triacetyl-α-D-arabinopyranoside(19186-37-9)
• EPA Substance Registry System: Acetyl 2-O,3-O,4-O-triacetyl-α-D-arabinopyranoside(19186-37-9)

Safety Data

• Hazardous Substances Data: 19186-37-9(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 532-20-7 D-arabinofuranose 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 68579-19-1 Acetic acid (2S,3R,4S,5R)-4,5-diacetoxy-2-(5,5-dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-ylsulfanyl)-tetrahydro-pyran-3-yl ester 
• 58-86-6 D-xylose 
• 75-36-5 acetyl chloride 
• 1195726-04-5 trans-2-ethoxy-3,4-epoxytetrahydropyran 
• 31080-85-0 trans-6-ethoxy-5-hydroxy-5,6-dihydro-2H-pyran 
• 10369-25-2 2,3,4-tri-O-acetyl-α,β-L-arabinopyranose 
• 87-72-9 L-(+)-arabinose 
• 127-09-3 sodium acetate 
• 5328-37-0 L-arabinose 
• 41546-21-8 L-ribose 

Downstream Products

• 1071555-74-2 (4-nitro-phenyl)-(tri-O-acetyl-α-D-arabinopyranoside) 
• 1195182-65-0 (4-nitro-phenyl)-(tri-O-acetyl-β-D-arabinopyranoside) 
• 3068-29-9 2,3,4-tri-O-acetyl-β-D-arabinosyl bromide 
• 4049-33-6 tetra-O-acetyl-β-D-xylopyranose 
• 94921-62-7 (4-nitro-phenyl)-(tri-O-acetyl-β-L-arabinopyranoside) 
• 94921-63-8 (4-nitro-phenyl)-(tri-O-acetyl-α-L-arabinopyranoside) 
• 3456-62-0 2-methylphenyl-α-L-arabinopyranoside 
• 14227-90-8 2,3,4-tri-O-acetyl-α-L-arabinopyranosyl bromide 
• 169304-01-2 Acetic acid (2R,3R,4S,5R)-4,5-diacetoxy-2-(3-cyano-4,6-diphenyl-2-thioxo-2H-pyridin-1-yl)-tetrahydro-pyran-3-yl ester 
• 169304-03-4 Acetic acid (2R,3R,4S,5R)-4,5-diacetoxy-2-(3-cyano-4-phenyl-2-thioxo-6-p-tolyl-2H-pyridin-1-yl)-tetrahydro-pyran-3-yl ester 
• 169304-06-7 Acetic acid (2R,3R,4S,5R)-4,5-diacetoxy-2-(3-cyano-4-furan-2-yl-2-thioxo-6-p-tolyl-2H-pyridin-1-yl)-tetrahydro-pyran-3-yl ester 
• 169304-04-5 Acetic acid (2R,3R,4S,5R)-4,5-diacetoxy-2-[3-cyano-4-(4-methoxy-phenyl)-6-phenyl-2-thioxo-2H-pyridin-1-yl]-tetrahydro-pyran-3-yl ester 
• 169304-07-8 Acetic acid (2R,3R,4S,5R)-4,5-diacetoxy-2-[3-cyano-4-furan-2-yl-6-(4-methoxy-phenyl)-2-thioxo-2H-pyridin-1-yl]-tetrahydro-pyran-3-yl ester 
• 107961-02-4 phenyl 2,3,4-tri-O-acetyl-1-thio-α-D-arabinopyranoside 

Relevant articles and documents

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Synthesis and biological evaluation of 3β-O-neoglycosides of caudatin and its analogues as potential anticancer agents

In order to study the structure–activity relationship (SAR) of C21-steroidal glycosides toward human cancer cell lines and explore more potential anticancer agents, a series of 3β-O-neoglycosides of caudatin and its analogues were synthesized. The results revealed that most of peracetylated 3β-O-monoglycosides demonstrated moderate to significant antiproliferative activities against four human cancer cell lines (MCF-7, HCT-116, HeLa, and HepG2). Among them, 3β-O-(2,3,4-tri-O-acetyl-β-L-glucopyranosyl)-caudatin (2k) exhibited the highest antiproliferative activity aganist HepG2 cells with an IC50 value of 3.11 μM. Mechanical studies showed that compound 2k induced both apoptosis and cell cycle arrest at S phase in a dose dependent manner. Overall, these present findings suggested that glycosylation is a promising scaffold to improve anticancer activity for naturally occurring C21-steroidal aglycones, and compound 2k represents a potential anticancer agent deserved further investigation.

Isolation and characterization of triterpenoid saponins from leaves of Aralia nudicaulis L

Three new oleanolic glycosides (1–3), along with seven known saponins from various plants (4–10) were isolated for the first time from the leaves of Aralia nudicaulis. Their structures were elucidated on the basis of spectroscopic evidence, including 1D and 2D NMR, and HRESIMS. Nudicauloside A and B (1–2) have shown moderate anti-inflammatory activity, as demonstrated by inhibition of LPS-induced NO production in raw 264.7 murine macrophages (IC50 = 74–101 μM).

Total Synthesis of (+)-Erogorgiaene and the Pseudopterosin A?F Aglycone via Enantioselective Cobalt-Catalyzed Hydrovinylation

Due to their pronounced bioactivity and limited availability from natural resources, metabolites of the soft coral Pseudopterogorgia elisabethae, such as erogorgiaene and the pseudopterosines, represent important target molecules for chemical synthesis. We have now developed a particularly short and efficient route towards these marine diterpenes exploiting an operationally convenient enantioselective cobalt-catalyzed hydrovinylation as the chirogenic step. Other noteworthy C?C bond forming transformations include diastereoselective Lewis acid-mediated cyclizations, a Suzuki coupling and a carbonyl ene reaction. Starting from 4-methyl-styrene the anti-tubercular agent (+)-erogorgiaene (>98 % ee) was prepared in only 7 steps with 46 % overall yield. In addition, the synthesis of the pseudopterosin A aglycone was achieved in 12 steps with 30 % overall yield and, surprisingly, was found to exhibit a similar anti-inflammatory activity (inhibition of LPS-induced NF-κB activation) as a natural mixture of pseudopterosins A?D or iso-pseudopterosin A, prepared by β-D-xylosylation of the synthetic aglycone.