Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(4-bromomethyl-benzylsulfanyl)-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(4-bromomethyl-benzylsulfanyl)-tetrahydro-pyran-4-yl ester
• CAS No.: 329717-42-2
• Molecular Formula: C₂₂H₂₇BrO₉S
• Molecular Weight: 547.421
• Mol file: 329717-42-2.mol

Synonyms:Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(4-bromomethyl-benzylsulfanyl)-tetrahydro-pyran-4-yl ester

Chemical Property of Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(4-bromomethyl-benzylsulfanyl)-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,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(4-bromomethyl-benzylsulfanyl)-tetrahydro-pyran-4-yl ester

There total 1 articles about Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(4-bromomethyl-benzylsulfanyl)-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: 90.0%

1,4-bis(bromomethyl)benzene (623-24-5) + tetraacetyl thioglucose (19879-84-6) → Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(4-bromomethyl-benzylsulfanyl)-tetrahydro-pyran-4-yl ester (329717-42-2)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1039/b008489l

Reference yield:

Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(4-bromomethyl-benzylsulfanyl)-tetrahydro-pyran-4-yl ester (329717-42-2) → 4-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-benzaldehyde (329717-50-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 60 percent / silver triflate; 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 3 h / 20 °C

2: sodium methoxide; methanol / 1 h / 20 °C

3: 402 mg / sodium hydride; tetrabutylammonium iodide / tetrahydrofuran; dimethylformamide; various solvent(s) / 8 h / 20 °C

4: 87 percent / magnesium monoperoxyphthalate hexahydrate / tetrahydrofuran; aq. ethanol / 2 h / 60 °C

5: CBr₂F₂; KOH/alumina / CH₂Cl₂; 2-methyl-propan-2-ol / 3 h / 0 - 20 °C

6: base

7: 95 percent / H₂ / Pd/alumina / ethyl acetate / 12 h / 20 °C

8: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

9: 85 percent / oxalyl chloride; DMSO; NEt₃ / CH₂Cl₂ / 1.5 h / -78 - 20 °C

With methanol; aluminum oxide; potassium hydroxide; 2,6-di-tert-butyl-4-methylpyridine; oxalyl dichloride; dibromodifluoromethane; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; silver trifluoromethanesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; magnesium monoperoxyphthalate hexahydrate; dimethyl sulfoxide; triethylamine; palladium/alumina; palladium; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol; 9: Swern oxidation;

DOI:10.1039/b008489l

Reference yield:

Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-(4-bromomethyl-benzylsulfanyl)-tetrahydro-pyran-4-yl ester (329717-42-2) → [4-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-phenyl]-methanol (329717-49-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 60 percent / silver triflate; 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 3 h / 20 °C

2: sodium methoxide; methanol / 1 h / 20 °C

3: 402 mg / sodium hydride; tetrabutylammonium iodide / tetrahydrofuran; dimethylformamide; various solvent(s) / 8 h / 20 °C

4: 87 percent / magnesium monoperoxyphthalate hexahydrate / tetrahydrofuran; aq. ethanol / 2 h / 60 °C

5: CBr₂F₂; KOH/alumina / CH₂Cl₂; 2-methyl-propan-2-ol / 3 h / 0 - 20 °C

6: base

7: 95 percent / H₂ / Pd/alumina / ethyl acetate / 12 h / 20 °C

8: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

With methanol; aluminum oxide; potassium hydroxide; 2,6-di-tert-butyl-4-methylpyridine; dibromodifluoromethane; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; silver trifluoromethanesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; magnesium monoperoxyphthalate hexahydrate; palladium/alumina; palladium; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1039/b008489l

upstream raw materials:

1,4-bis(bromomethyl)benzene

tetraacetyl thioglucose

Downstream raw materials:

tert-Butyl-dimethyl-{4-[(3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-(2Z)-ylidenemethyl]-benzyloxy}-silane

4-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-benzaldehyde

[4-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-phenyl]-methanol

tert-Butyl-dimethyl-[4-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-benzyloxy]-silane