(2R,3S,4R)-4-((Triisopropylsilyl)oxy)-2-(((triisopropylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3-ol

Base Information

• Chemical Name: (2R,3S,4R)-4-((Triisopropylsilyl)oxy)-2-(((triisopropylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3-ol
• CAS No.: 201053-37-4
• Molecular Formula: C24H50 O4 Si2
• Molecular Weight: 458.83
• DSSTox Substance ID: DTXSID30442939
• Wikidata: Q82260557
• Mol file: 201053-37-4.mol

Synonyms:201053-37-4;(2R,3S,4R)-4-Tri(propan-2-yl)silyloxy-2-[tri(propan-2-yl)silyloxymethyl]-3,4-dihydro-2H-pyran-3-ol;(2R,3S,4R)-4-((Triisopropylsilyl)oxy)-2-(((triisopropylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3-ol;DTXSID30442939;AKOS015914066;3,6-Di-O-(triisopropylsilyl)-D-galactal, AldrichCPR;2,6-Anhydro-5-deoxy-1,4-bis-O-[tri(propan-2-yl)silyl]-D-arabino-hex-5-enitol

Chemical Property of (2R,3S,4R)-4-((Triisopropylsilyl)oxy)-2-(((triisopropylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3-ol

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: n20/D 1.48(lit.)
• Boiling Point: 462.076°C at 760 mmHg
• Flash Point: >230 °F
• PSA: 47.92000
• Density: 0.965 g/mL at 25 °C(lit.)
• LogP: 7.01260
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 11
• Exact Mass: 458.32476314
• Heavy Atom Count: 30
• Complexity: 500

Purity/Quality:

97% ^*data from raw suppliers

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)O
• 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)O

Technology Process of (2R,3S,4R)-4-((Triisopropylsilyl)oxy)-2-(((triisopropylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3-ol

There total 4 articles about (2R,3S,4R)-4-((Triisopropylsilyl)oxy)-2-(((triisopropylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3-ol 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: 93.0%

triisopropylsilyl chloride (13154-24-0) + D-galactal (21193-75-9) → (-)-3,6-O-bis(triisopropylsilyl)-D-galactal (201053-37-4)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 60 ℃; for 48h;

DOI:10.3390/molecules27061764

Reference yield: 85.0%

triisopropylsilyl chloride (13154-24-0) + triacetyl-D-galactal (4098-06-0) → (-)-3,6-O-bis(triisopropylsilyl)-D-galactal (201053-37-4)

Guidance literature:

triacetyl-D-galactal; With methanol; sodium methylate; at 20 ℃; for 1h;

triisopropylsilyl chloride; With 1H-imidazole; In N,N-dimethyl-formamide; at 60 ℃; for 18h;

DOI:10.1016/j.tetasy.2004.11.048

Reference yield:

triacetyl-D-galactal (4098-06-0) → (-)-3,6-O-bis(triisopropylsilyl)-D-galactal (201053-37-4)

Guidance literature:

Multi-step reaction with 3 steps

1: NH₃ / methanol

2: Im / dimethylformamide

3: 62 percent / imidazole / dimethylformamide

With 1H-imidazole; impramine; ammonia; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/ja9724957

upstream raw materials:

triisopropylsilyl chloride

triacetyl-D-galactal

D-galactal

Downstream raw materials:

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

Acetic acid (2R,3S,4R)-4-triisopropylsilanyloxy-2-triisopropylsilanyloxymethyl-3,4-dihydro-2H-pyran-3-yl ester

3,4,6-tri-O-(triisopropylsilyl)-D-galactal

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