4-O-Acetyl-3,6-di-O-(triisopropylsilyl)-D-galactal

Base Information

• Chemical Name: 4-O-Acetyl-3,6-di-O-(triisopropylsilyl)-D-galactal
• CAS No.: 201053-38-5
• Molecular Formula: C26H52 O5 Si2
• Molecular Weight: 500.867
• DSSTox Substance ID: DTXSID30446275
• Nikkaji Number: J970.675E
• Wikidata: Q82264886
• Mol file: 201053-38-5.mol

Synonyms:201053-38-5;4-O-Acetyl-3,6-di-O-(triisopropylsilyl)-D-galactal;[(2R,3S,4R)-4-tri(propan-2-yl)silyloxy-2-[tri(propan-2-yl)silyloxymethyl]-3,4-dihydro-2H-pyran-3-yl] acetate;DTXSID30446275;4-O-Acetyl-3,6-di-O-(triisopropylsilyl)-D-galactal, AldrichCPR;(2R,3S,4R)-4-((Triisopropylsilyl)oxy)-2-(((triisopropylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3-yl acetate;(2R,3S,4R)-4-((Triisopropylsilyl)oxy)-2-(((triisopropylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3-ylacetate;Acetic acid (2R)-2alpha-[(triisopropylsiloxy)methyl]-4alpha-(triisopropylsiloxy)-3,4-dihydro-2H-pyran-3alpha-yl ester

Chemical Property of 4-O-Acetyl-3,6-di-O-(triisopropylsilyl)-D-galactal

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: n20/D 1.475(lit.)
• Boiling Point: 477.9°Cat760mmHg
• Flash Point: 201.7°C
• PSA: 53.99000
• Density: 0.95g/cm³
• LogP: 7.58340
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 13
• Exact Mass: 500.33532782
• Heavy Atom Count: 33
• Complexity: 599

Purity/Quality:

97% ^*data from raw suppliers

4-O-Acetyl-3,6-di-O-(triisopropylsilyl)-D-galactal Aldrich ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)[Si](C(C)C)(C(C)C)OCC1C(C(C=CO1)O[Si](C(C)C)(C(C)C)C(C)C)OC(=O)C
• Isomeric SMILES: CC(C)[Si](C(C)C)(C(C)C)OC[C@@H]1[C@@H]([C@@H](C=CO1)O[Si](C(C)C)(C(C)C)C(C)C)OC(=O)C

Technology Process of 4-O-Acetyl-3,6-di-O-(triisopropylsilyl)-D-galactal

There total 5 articles about 4-O-Acetyl-3,6-di-O-(triisopropylsilyl)-D-galactal 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%

acetic anhydride (108-24-7) + (-)-3,6-O-bis(triisopropylsilyl)-D-galactal (201053-37-4) → Acetic acid (2R,3S,4R)-4-triisopropylsilanyloxy-2-triisopropylsilanyloxymethyl-3,4-dihydro-2H-pyran-3-yl ester (201053-38-5)

Guidance literature:

In pyridine; Ambient temperature;

DOI:10.1016/S0040-4020(98)00281-6

Reference yield:

D-galactal (21193-75-9) → Acetic acid (2R,3S,4R)-4-triisopropylsilanyloxy-2-triisopropylsilanyloxymethyl-3,4-dihydro-2H-pyran-3-yl ester (201053-38-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

2: 100 percent / pyridine / Ambient temperature

With 1H-imidazole; In pyridine; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(98)00281-6

Reference yield:

1,5-anhydro-6-O-triisopropylsilyl-2-deoxy-D-lyxo-hex-1-enitol (166021-01-8) → Acetic acid (2R,3S,4R)-4-triisopropylsilanyloxy-2-triisopropylsilanyloxymethyl-3,4-dihydro-2H-pyran-3-yl ester (201053-38-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 62 percent / imidazole / dimethylformamide

2: 89 percent / pyridine, DMAP

With pyridine; 1H-imidazole; dmap; In N,N-dimethyl-formamide;

DOI:10.1021/ja9724957

upstream raw materials:

acetic anhydride

(-)-3,6-O-bis(triisopropylsilyl)-D-galactal

triisopropylsilyl chloride

D-galactal

Downstream raw materials:

Acetic acid (2R,3S,4S,5S,6S)-6-benzenesulfonylamino-5-iodo-4-triisopropylsilanyloxy-2-triisopropylsilanyloxymethyl-tetrahydro-pyran-3-yl ester

N-((2S,3R,4R,5S,6R)-2-Ethylsulfanyl-5-hydroxy-4-triisopropylsilanyloxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-3-yl)-benzenesulfonamide

Acetic acid (2R,3S,4R,5R,6S)-5-benzenesulfonylamino-6-ethylsulfanyl-4-triisopropylsilanyloxy-2-triisopropylsilanyloxymethyl-tetrahydro-pyran-3-yl ester

N-[(2S,3R,4R,5S,6R)-2-((2R,3R,4R)-4-Benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran-3-yloxy)-5-hydroxy-4-triisopropylsilanyloxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-3-yl]-benzenesulfonamide