203179-64-0

Basic information

• Product Name: (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-((E)-3-hydroxyprop-1-en-1 -yl)-2,6-dimethoxyphenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• Synonyms: (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-((E)-3-hydroxyprop-1-en-1 -yl)-2,6-dimethoxyphenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS NO: 203179-64-0
• Molecular Weight: 540.521
• Mol File: 203179-64-0.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-((E)-3-hydroxyprop-1-en-1 -yl)-2,6-dimethoxyphenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-((E)-3-hydroxyprop-1-en-1 -yl)-2,6-dimethoxyphenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate(203179-64-0)
• EPA Substance Registry System: (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-((E)-3-hydroxyprop-1-en-1 -yl)-2,6-dimethoxyphenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate(203179-64-0)

Safety Data

• Hazardous Substances Data: 203179-64-0(Hazardous Substances Data)

Upstream product

• 20675-96-1 Syringenin 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 69113-98-0 4-hydroxy-3,5-dimethoxycinnamic acid ethyl ester 
• 530-59-6 sinapinic acid 
• 41628-47-1 ethyl (2E)-3-[4-hydroxy-3,5-bis(methyloxy)phenyl]-2-propenoate 
• 2280-44-6 D-Glucose 
• 530-59-6 trans-3,5-dimethoxy-4-hydroxycinnamic acid 
• 20675-96-1 trans-sinapyl alcohol 
• 134-96-3 syringic aldehyde 
• 117685-21-9 3,5-dimethoxy-4-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)benzaldehyde 
• 83-87-4 D-glucose pentaacetate 
• 203179-62-8 3,5-dimethoxy-4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-trans-cinnamaldehyde 

Downstream Products

• 118-34-3 syringin 

Relevant articles and documents

First total syntheses of two natural glycosides

Isosyringinoside (1) and 3-(O-β-D-glucopyranosyl)-α-(O-β-D-glucopyranosyl)-4-hydroxy phenylethanol (2), the natural bioactive compounds contained unique structures, were first totally synthesized using easily available materials in short convenient routes with overall yields of 20.2% and 27.0%, respectively. An efficient total synthesis of 1 was developed in six steps, which contained two key steps of highly regioselective glycosylation without any selective protection steps. The seven-step synthesis of 2 involved two steps of regioselective glycosylations using BF3–O(C2H5)2 and TMSOTf as catalysts, respectively.

Total Syntheses and Anti-inflammatory Activities of Syringin and Its Natural Analogues

Syringin (1), a natural bioactive glucoside isolated from the root of Acanthopanax senticosus (Rupr. Maxim.) Harms, possesses significant anti-inflammatory activity. In this study, we have accomplished the total syntheses of syringin (1), along with its natural analogues 2-12, from a common starting material, syringaldehyde (13), in 4-8 steps with an overall yields of 11.8-61.3%. The anti-inflammatory activities of these compounds were determined against NO production in the LPS-stimulated RAW264.7 cells. Among them, compounds 1-5, 7, and 9 exhibited different levels of anti-inflammatory activity.