6-O-(TERT-BUTYLDIMETHYLSILYL)-D-GALACTAL CYCLIC CARBONATE

Base Information

• Chemical Name: 6-O-(TERT-BUTYLDIMETHYLSILYL)-D-GALACTAL CYCLIC CARBONATE
• CAS No.: 163228-38-4
• Molecular Formula: C13H22 O5 Si
• Molecular Weight: 286.4
• Mol file: 163228-38-4.mol

Synonyms:6-O-(TERT-BUTYLDIMETHYLSILYL)-D-GALACTAL CYCLIC CARBONATE;6-O-(tert-butyldimethylsilyl)-D-galactal cyclic C

Chemical Property of 6-O-(TERT-BUTYLDIMETHYLSILYL)-D-GALACTAL CYCLIC CARBONATE

Chemical Property:

• Melting Point: 45-49 °C(lit.)
• Flash Point: >230 °F
• PSA: 102.29000
• LogP: 0.83290

Purity/Quality:

95% ^*data from raw suppliers

6-O-(tert-Butyldimethylsilyl)-D-galactal cyclic carbonate Aldrich ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

Technology Process of 6-O-(TERT-BUTYLDIMETHYLSILYL)-D-GALACTAL CYCLIC CARBONATE

There total 4 articles about 6-O-(TERT-BUTYLDIMETHYLSILYL)-D-GALACTAL CYCLIC CARBONATE 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: 82.0%

(2R,3R,4R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol (124751-19-5) + 1,1'-carbonyldiimidazole (530-62-1) → 2,6-anhydro-1-O-[tert-butyl(dimethyl)silyl]-5-deoxy-3,4-O-(oxomethylene)-D-arabino-hex-5-enitol (163228-38-4)

Guidance literature:

With 1H-imidazole; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1021/ja00112a007

Reference yield: 51.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 1,1'-carbonyldiimidazole (530-62-1) + triacetyl-D-galactal (4098-06-0) → 2,6-anhydro-1-O-[tert-butyl(dimethyl)silyl]-5-deoxy-3,4-O-(oxomethylene)-D-arabino-hex-5-enitol (163228-38-4)

Guidance literature:

triacetyl-D-galactal; With sodium methylate; In methanol; DClO₄; at 29 ℃; for 2h;

tert-butyldimethylsilyl chloride; With 1H-imidazole; In dichloromethane; at 0 - 28 ℃; for 1.5h;

1,1'-carbonyldiimidazole; In tetrahydrofuran; at 0 - 28 ℃; for 20h;

DOI:10.1021/acs.joc.0c01170

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 2,6-anhydro-1-O-[tert-butyl(dimethyl)silyl]-5-deoxy-3,4-O-(oxomethylene)-D-arabino-hex-5-enitol (163228-38-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / imidazole / dimethylformamide / Ambient temperature

2: 82 percent / imidazole / tetrahydrofuran / 2 h / Ambient temperature

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

DOI:10.1021/ja00112a007

upstream raw materials:

(2R,3R,4R)-2-(((tert-butyldimethylsilyl)oxy)methyl)-3,4-dihydro-2H-pyran-3,4-diol

1,1'-carbonyldiimidazole

tert-butyldimethylsilyl chloride

D-galactal

Downstream raw materials:

methyl 2,3-dideoxy-4,6-di-O-benzoyl-β-D-threo-hex-2-enopyranoside

1,5-anhydro-6-O-benzyl-3,4-O-carbonate-2-deoxy-D-lyxo-hex-1-enopyranose