Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[2-(1-hydroxy-4-oxo-cyclohexa-2,5-dienyl)-ethoxy]-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[2-(1-hydroxy-4-oxo-cyclohexa-2,5-dienyl)-ethoxy]-tetrahydro-pyran-4-yl ester
• CAS No.: 40593-03-1
• Molecular Formula: C₂₂H₂₈O₁₂
• Molecular Weight: 484.457
• Mol file: 40593-03-1.mol

Synonyms:

Chemical Property of Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[2-(1-hydroxy-4-oxo-cyclohexa-2,5-dienyl)-ethoxy]-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[2-(1-hydroxy-4-oxo-cyclohexa-2,5-dienyl)-ethoxy]-tetrahydro-pyran-4-yl ester

There total 10 articles about Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[2-(1-hydroxy-4-oxo-cyclohexa-2,5-dienyl)-ethoxy]-tetrahydro-pyran-4-yl ester 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: 11.5%

tetraacetyl salidroside (28251-63-0) → Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[2-(1-hydroxy-4-oxo-cyclohexa-2,5-dienyl)-ethoxy]-tetrahydro-pyran-4-yl ester (40593-03-1)

Guidance literature:

With thallium(III) perchlorate; In dichloromethane; for 0.25h;

DOI:10.1248/cpb.46.581

Reference yield:

4-Methoxyphenylacetic acid (104-01-8) → Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[2-(1-hydroxy-4-oxo-cyclohexa-2,5-dienyl)-ethoxy]-tetrahydro-pyran-4-yl ester (40593-03-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 93 percent / BBr₃ / CH₂Cl₂ / 0.5 h / -78 °C

2: 95 percent / concd aq. HCl / 0.5 h / Heating

3: 90 percent / NaBH₄ / H₂O / 8 h / Ambient temperature

4: 73 percent / 1N aq. NaOH / tetrahydrofuran / 1 h / Ambient temperature

5: 1.) Ag₂CO₃, Drierite, 2.) I₂ / 1.) Et₂O, RT, 10 min, 2.) Et₂O, RT, 14 h

6: 43.3 percent / Zn, MeOH / 4.2 h / Ambient temperature

7: 11.5 percent / aq. thallium triperchlorate / CH₂Cl₂ / 0.25 h

With hydrogenchloride; methanol; calcium sulfate; sodium hydroxide; sodium tetrahydroborate; thallium(III) perchlorate; iodine; boron tribromide; silver carbonate; zinc; In tetrahydrofuran; dichloromethane; water;

DOI:10.1248/cpb.46.581

Reference yield:

4-hydroxyphenylacetate (156-38-7) → Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-[2-(1-hydroxy-4-oxo-cyclohexa-2,5-dienyl)-ethoxy]-tetrahydro-pyran-4-yl ester (40593-03-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 95 percent / concd aq. HCl / 0.5 h / Heating

2: 90 percent / NaBH₄ / H₂O / 8 h / Ambient temperature

3: 73 percent / 1N aq. NaOH / tetrahydrofuran / 1 h / Ambient temperature

4: 1.) Ag₂CO₃, Drierite, 2.) I₂ / 1.) Et₂O, RT, 10 min, 2.) Et₂O, RT, 14 h

5: 43.3 percent / Zn, MeOH / 4.2 h / Ambient temperature

6: 11.5 percent / aq. thallium triperchlorate / CH₂Cl₂ / 0.25 h

With hydrogenchloride; methanol; calcium sulfate; sodium hydroxide; sodium tetrahydroborate; thallium(III) perchlorate; iodine; silver carbonate; zinc; In tetrahydrofuran; dichloromethane; water;

DOI:10.1248/cpb.46.581

upstream raw materials:

tetraacetyl salidroside

4-Methoxyphenylacetic acid

4-hydroxyphenylacetate

(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(4-acetoxyphenethoxy)tetrahydro-2Hpyran-3,4,5-triyl triacetate

Downstream raw materials:

rengyoside B

cornoside