(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-{[1-(3,4,5-trimethoxyphenyl)vinyl]thio}tetrahydro-2H-pyran-3,4,5-triyl triacetate

Base Information

• Chemical Name: (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-{[1-(3,4,5-trimethoxyphenyl)vinyl]thio}tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS No.: 1467023-91-1
• Molecular Formula: C₂₅H₃₂O₁₂S
• Molecular Weight: 556.588
• Mol file: 1467023-91-1.mol

Synonyms:(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-{[1-(3,4,5-trimethoxyphenyl)vinyl]thio}tetrahydro-2H-pyran-3,4,5-triyl triacetate

Chemical Property of (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-{[1-(3,4,5-trimethoxyphenyl)vinyl]thio}tetrahydro-2H-pyran-3,4,5-triyl triacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-{[1-(3,4,5-trimethoxyphenyl)vinyl]thio}tetrahydro-2H-pyran-3,4,5-triyl triacetate

There total 4 articles about (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-{[1-(3,4,5-trimethoxyphenyl)vinyl]thio}tetrahydro-2H-pyran-3,4,5-triyl triacetate 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: 76.0%

1-iodo-1-(3,4,5-trimethoxyphenyl)ethylene + tetraacetyl thioglucose (19879-84-6) → (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-{[1-(3,4,5-trimethoxyphenyl)vinyl]thio}tetrahydro-2H-pyran-3,4,5-triyl triacetate (1467023-91-1)

Guidance literature:

With palladium diacetate; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; at 75 ℃; for 1h; diastereoselective reaction; Schlenk technique; Inert atmosphere; Sealed tube;

DOI:10.1002/adsc.201300419

Reference yield:

D-glucose pentaacetate (83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5) → (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-{[1-(3,4,5-trimethoxyphenyl)vinyl]thio}tetrahydro-2H-pyran-3,4,5-triyl triacetate (1467023-91-1)

Guidance literature:

Multi-step reaction with 4 steps

1: hydrogen bromide; acetic acid / dichloromethane / 3 h / 20 °C

2: acetone / 2 h / Reflux

3: sodium meta bi sulfate / dichloromethane; water / 3 h / Reflux

4: C₅₁H₄₂NOP₂Pd⁽¹⁺⁾*CH₃O₃S^(1-); triethylamine / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

With sodium meta bi sulfate; C₅₁H₄₂NOP₂Pd⁽¹⁺⁾*CH₃O₃S^(1-); hydrogen bromide; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane; water; acetone;

DOI:10.1002/chem.201501050

Reference yield:

C15H22N2O9S*BrH → (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-{[1-(3,4,5-trimethoxyphenyl)vinyl]thio}tetrahydro-2H-pyran-3,4,5-triyl triacetate (1467023-91-1)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium meta bi sulfate / dichloromethane; water / 3 h / Reflux

2: C₅₁H₄₂NOP₂Pd⁽¹⁺⁾*CH₃O₃S^(1-); triethylamine / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

With sodium meta bi sulfate; C₅₁H₄₂NOP₂Pd⁽¹⁺⁾*CH₃O₃S^(1-); triethylamine; In tetrahydrofuran; dichloromethane; water;

DOI:10.1002/chem.201501050

upstream raw materials:

tetraacetyl thioglucose

D-glucose pentaacetate

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