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

Base Information

• Chemical Name: 4-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-benzaldehyde
• CAS No.: 329717-50-2
• Molecular Formula: C₄₂H₄₂O₆
• Molecular Weight: 642.792
• Mol file: 329717-50-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about 4-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-benzaldehyde 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: 97.0%

[4-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-phenyl]-methanol (329717-49-9) → 4-((2S,3S,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-benzaldehyde (329717-50-2)

Guidance literature:

With manganese(IV) oxide; In chloroform; at 20 ℃; for 2h; Heating / reflux;

Reference yield:

tert-Butyl-dimethyl-{4-[(3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-(2Z)-ylidenemethyl]-benzyloxy}-silane (329717-46-6) → 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 3 steps

1: 95 percent / H₂ / Pd/alumina / ethyl acetate / 12 h / 20 °C

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

3: 85 percent / oxalyl chloride; DMSO; NEt₃ / CH₂Cl₂ / 1.5 h / -78 - 20 °C

With oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; palladium/alumina; palladium; In tetrahydrofuran; dichloromethane; ethyl acetate; 3: Swern oxidation;

DOI:10.1039/b008489l

Reference yield:

1,4-bis(bromomethyl)benzene (623-24-5) → 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 10 steps

1: 90 percent / NaH / tetrahydrofuran; various solvent(s) / 2 h / 20 °C

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

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

4: 402 mg / sodium hydride; tetrabutylammonium iodide / tetrahydrofuran; dimethylformamide; various solvent(s) / 8 h / 20 °C

5: 87 percent / magnesium monoperoxyphthalate hexahydrate / tetrahydrofuran; aq. ethanol / 2 h / 60 °C

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

7: base

8: 95 percent / H₂ / Pd/alumina / ethyl acetate / 12 h / 20 °C

9: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

10: 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; 10: Swern oxidation;

DOI:10.1039/b008489l

upstream raw materials:

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

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

1,4-bis(bromomethyl)benzene

tetraacetyl thioglucose