2-trichloromethyl-4,5-dihydro-(2-azido-2,4,6-trideoxy-1-O-tert-butyldiphenylsilyl-β-D-allopyranoso)[3,4-d]-1,3-oxazole

Base Information

Chemical Name:2-trichloromethyl-4,5-dihydro-(2-azido-2,4,6-trideoxy-1-O-tert-butyldiphenylsilyl-β-D-allopyranoso)[3,4-d]-1,3-oxazole
CAS No.:1384556-75-5
Molecular Formula:C₂₄H₂₇Cl₃N₄O₃Si
Molecular Weight:553.948
Hs Code.:

Synonyms:2-trichloromethyl-4,5-dihydro-(2-azido-2,4,6-trideoxy-1-O-tert-butyldiphenylsilyl-β-D-allopyranoso)[3,4-d]-1,3-oxazole

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Chemical Property of 2-trichloromethyl-4,5-dihydro-(2-azido-2,4,6-trideoxy-1-O-tert-butyldiphenylsilyl-β-D-allopyranoso)[3,4-d]-1,3-oxazole

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Technology Process of 2-trichloromethyl-4,5-dihydro-(2-azido-2,4,6-trideoxy-1-O-tert-butyldiphenylsilyl-β-D-allopyranoso)[3,4-d]-1,3-oxazole

There total 9 articles about 2-trichloromethyl-4,5-dihydro-(2-azido-2,4,6-trideoxy-1-O-tert-butyldiphenylsilyl-β-D-allopyranoso)[3,4-d]-1,3-oxazole 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: 63.0%

: 1384556-70-0
tert-butyldiphenylsilyl 2-azido-2,6-dideoxy-β-D-glucopyranoside

: 545-06-2
trichloroacetonitrile

: 1384556-75-5
2-trichloromethyl-4,5-dihydro-(2-azido-2,4,6-trideoxy-1-O-tert-butyldiphenylsilyl-β-D-allopyranoso)[3,4-d]-1,3-oxazole

: 1384556-72-2
2-trichloromethyl-4,5-dihydro-(2-azido-2,4,6-trideoxy-1-O-tert-butyldiphenylsilyl-β-D-galactopyranoso)[4,3-d]-1,3-oxazole

Guidance literature:: tert-butyldiphenylsilyl 2-azido-2,6-dideoxy-β-D-glucopyranoside; trichloroacetonitrile; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at -13 ℃; for 1h; Molecular sieve;

With pyridine; trifluoromethylsulfonic anhydride; In dichloromethane; at -30 - 20 ℃; Molecular sieve;

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; Molecular sieve;
DOI:10.1016/j.carres.2012.02.015

Reference yield:

: 344403-81-2
(2R,3S,4R,5R,6S)-2-(acetoxymethyl)-5-azido-6-((tert-butyldiphenylsilyl)oxy)tetrahydro-2H-pyran-3,4-diyl diacetate

: 1384556-75-5
2-trichloromethyl-4,5-dihydro-(2-azido-2,4,6-trideoxy-1-O-tert-butyldiphenylsilyl-β-D-allopyranoso)[3,4-d]-1,3-oxazole

: 1384556-72-2
2-trichloromethyl-4,5-dihydro-(2-azido-2,4,6-trideoxy-1-O-tert-butyldiphenylsilyl-β-D-galactopyranoso)[4,3-d]-1,3-oxazole

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium methylate / methanol; dichloromethane

2.1: pyridine / 2 h / 0 °C

3.1: sodium iodide / butanone / 6 h / Reflux

4.1: sodium cyanoborohydride / diethylene glycol dimethyl ether / 7 h / Reflux

5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / -13 °C / Molecular sieve

5.2: -30 - 20 °C / Molecular sieve

5.3: 20 °C / Molecular sieve

With sodium methylate; sodium cyanoborohydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium iodide; In pyridine; methanol; dichloromethane; diethylene glycol dimethyl ether; butanone;
DOI:10.1016/j.carres.2012.02.015

Reference yield:

: 501088-46-6
tert-butyldiphenylsilyl 2-azido-2-deoxy-β-D-glucopyranoside

: 1384556-75-5
2-trichloromethyl-4,5-dihydro-(2-azido-2,4,6-trideoxy-1-O-tert-butyldiphenylsilyl-β-D-allopyranoso)[3,4-d]-1,3-oxazole

: 1384556-72-2
2-trichloromethyl-4,5-dihydro-(2-azido-2,4,6-trideoxy-1-O-tert-butyldiphenylsilyl-β-D-galactopyranoso)[4,3-d]-1,3-oxazole

Guidance literature:: Multi-step reaction with 4 steps

1.1: pyridine / 2 h / 0 °C

2.1: sodium iodide / butanone / 6 h / Reflux

3.1: sodium cyanoborohydride / diethylene glycol dimethyl ether / 7 h / Reflux

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / -13 °C / Molecular sieve

4.2: -30 - 20 °C / Molecular sieve

4.3: 20 °C / Molecular sieve

With sodium cyanoborohydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium iodide; In pyridine; dichloromethane; diethylene glycol dimethyl ether; butanone;
DOI:10.1016/j.carres.2012.02.015