6-O-(Triisopropylsilyl)-D-galactal

Base Information

• Chemical Name: 6-O-(Triisopropylsilyl)-D-galactal
• CAS No.: 166021-01-8
• Molecular Formula: C15H30 O4 Si
• Molecular Weight: 302.486
• DSSTox Substance ID: DTXSID00446207
• Nikkaji Number: J2.481.528E
• Wikidata: Q82264801
• Mol file: 166021-01-8.mol

Synonyms:6-O-(Triisopropylsilyl)-D-galactal;166021-01-8;(2R,3R,4R)-2-[tri(propan-2-yl)silyloxymethyl]-3,4-dihydro-2H-pyran-3,4-diol;(2R,3R,4R)-2-(((Triisopropylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol;T1935;DTXSID00446207;VYZHAYQIZWKLNP-RBSFLKMASA-N;HY-W115895;CS-0213563;D92548;1,5-Anhydro-2-deoxy-6-O-(triisopropylsilyl)-D-lyxo-hex-1-enitol;6-O-(Triisopropylsilyl)-1,5-anhydro-2-deoxy-D-lyxo-1-hexenitol;2,6-Anhydro-5-deoxy-1-O-[tri(propan-2-yl)silyl]-D-arabino-hex-5-enitol

Chemical Property of 6-O-(Triisopropylsilyl)-D-galactal

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: n20/D 1.488(lit.)
• Boiling Point: 361.886°C at 760 mmHg
• PKA: 12.78±0.60(Predicted)
• Flash Point: 113 °C
• PSA: 107.22000
• Density: 1.016g/cm³
• LogP: 0.82100
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 302.19133597
• Heavy Atom Count: 20
• Complexity: 306

Purity/Quality:

98%,99%, ^*data from raw suppliers

6-O-(Triisopropylsilyl)-D-galactal ^*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)O
• Isomeric SMILES: CC(C)[Si](C(C)C)(C(C)C)OC[C@@H]1[C@@H]([C@@H](C=CO1)O)O

Technology Process of 6-O-(Triisopropylsilyl)-D-galactal

There total 3 articles about 6-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: 96.0%

C19H34O6Si → 1,5-anhydro-6-O-triisopropylsilyl-2-deoxy-D-lyxo-hex-1-enitol (166021-01-8)

Guidance literature:

With methanol; potassium permanganate; trimethylsulphonium iodide; at 25 ℃; under 760.051 Torr; chemoselective reaction;

DOI:10.1039/d1ra03209g

Reference yield:

triisopropylsilyl chloride (13154-24-0) + D-galactal (21193-75-9) → 1,5-anhydro-6-O-triisopropylsilyl-2-deoxy-D-lyxo-hex-1-enitol (166021-01-8)

Guidance literature:

With impramine; In N,N-dimethyl-formamide; Yield given;

DOI:10.1021/ja9724957

Reference yield:

triacetyl-D-galactal (4098-06-0) → 1,5-anhydro-6-O-triisopropylsilyl-2-deoxy-D-lyxo-hex-1-enitol (166021-01-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 0.73 g / MeONa / methanol / 24 h / 20 °C

2: 1.2 g / imidazole / dimethylformamide / 12 h

With 1H-imidazole; sodium methylate; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)01163-2

upstream raw materials:

triisopropylsilyl chloride

D-galactal

triacetyl-D-galactal

Downstream raw materials:

O-(2-azido-2-deoxy-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)(1->3)-6-O-(triisopropylsilyl)-D-galactal

O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-(1->3)-6-O-(triisopropylsilyl)-D-galactal

O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->3)-6-O-(triisopropylsilyl)-D-galactal

O-(3,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-2-nitro-α-D-galactopyranosyl)-(1->3)-6-O-(triisopropylsilyl)-D-galactal

Refernces

• 1、 Gurawa, Aakanksha,Kashyap, Sudhir,Kumar, Manoj. "Me3SI-promoted chemoselective deacetylation: a general and mild protocol". . p. 19310 - 19315. Retrieved 2021/06/03.
• 2、 Medina, Sandra,Harper, Matthew J.,Balmond, Edward I.,Miranda, Silvia,Crisenza, Giacomo E. M.,Coe, Diane M.,McGarrigle, Eoghan M.,Galan, M. Carmen. "Stereoselective glycosylation of 2-nitrogalactals catalyzed by a bifunctional organocatalyst". supporting information. p. 4222 - 4225. Retrieved 2016/09/09.