(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(3-hydroxyprop-1-enyl)-2,6-dimethoxyphenoxy]oxane-3,4,5-triol

Base Information

• Chemical Name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(3-hydroxyprop-1-enyl)-2,6-dimethoxyphenoxy]oxane-3,4,5-triol
• CAS No.: 133815-42-6
• Molecular Formula: C₁₇H₂₄O₉
• Molecular Weight: 372.372
• Mol file: 133815-42-6.mol

Synonyms:(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(3-hydroxyprop-1-enyl)-2,6-dimethoxyphenoxy]oxane-3,4,5-triol

Chemical Property of (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(3-hydroxyprop-1-enyl)-2,6-dimethoxyphenoxy]oxane-3,4,5-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(3-hydroxyprop-1-enyl)-2,6-dimethoxyphenoxy]oxane-3,4,5-triol

There total 23 articles about (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(3-hydroxyprop-1-enyl)-2,6-dimethoxyphenoxy]oxane-3,4,5-triol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(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) → syringin (118-34-3,116965-45-8,133815-42-6)

Guidance literature:

With sodium methylate; In methanol; for 3h;

DOI:10.1055/s-1998-2009

Reference yield: 30.4%

3,5-dimethoxy-4-β-D-glucopyranosyloxycinnamic acid ethyl ester → (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(3-hydroxyprop-1-enyl)-2,6-dimethoxyphenoxy]oxane-3,4,5-triol (133815-42-6)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at -10 - 0 ℃;

DOI:10.1080/14786410902830175

Reference yield:

dilatioside B → Oleoside dimethyl ester (30164-95-5) + syringin (118-34-3,116965-45-8,133815-42-6)

Guidance literature:

With methanol; water; potassium hydroxide; at 20 ℃; for 1h; Overall yield = 0.6 mg;

DOI:10.1248/cpb.c16-00804

upstream raw materials:

3,5-dimethoxy-4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-trans-cinnamaldehyde

trans-sinapyl alcohol

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

tangshenoside I

Downstream raw materials:

trans-sinapyl alcohol

D-glucose

Syringenin

syringin penta-acetate