2,4-di-O-acetyl-6-azido-3-O-benzyl-6-deoxy-α-L-idopyranosyl trichloroacetimidate

Base Information

Chemical Name:2,4-di-O-acetyl-6-azido-3-O-benzyl-6-deoxy-α-L-idopyranosyl trichloroacetimidate
CAS No.:477329-89-8
Molecular Formula:C₁₉H₂₁Cl₃N₄O₇
Molecular Weight:523.757
Hs Code.:

Synonyms:2,4-di-O-acetyl-6-azido-3-O-benzyl-6-deoxy-α-L-idopyranosyl trichloroacetimidate

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Chemical Property of 2,4-di-O-acetyl-6-azido-3-O-benzyl-6-deoxy-α-L-idopyranosyl trichloroacetimidate

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Technology Process of 2,4-di-O-acetyl-6-azido-3-O-benzyl-6-deoxy-α-L-idopyranosyl trichloroacetimidate

There total 7 articles about 2,4-di-O-acetyl-6-azido-3-O-benzyl-6-deoxy-α-L-idopyranosyl trichloroacetimidate 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:

: 545-06-2
trichloroacetonitrile

: Acetic acid (2S,3R,4S,5R)-5-acetoxy-2-azidomethyl-4-benzyloxy-6-hydroxy-tetrahydro-pyran-3-yl ester

: 477329-89-8
2,4-di-O-acetyl-6-azido-3-O-benzyl-6-deoxy-α-L-idopyranosyl trichloroacetimidate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃;
DOI:10.1021/ol026588r

Reference yield:

: 2-Azido-1-((3aR,5S,6R,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethanone

: 477329-89-8
2,4-di-O-acetyl-6-azido-3-O-benzyl-6-deoxy-α-L-idopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 2.57 g / NaBH₄ / methanol / 0 °C

2.1: AcOH; H₂O; TFA / 2 h / 60 °C

2.2: 43 percent / TFA / 20 °C

3.1: hydrazine acetate / dimethylformamide / 20 °C

4.1: DBU / CH₂Cl₂ / 20 °C

With sodium tetrahydroborate; water; hydrazinium monoacetate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol026588r

Reference yield:

: 23313-05-5
6-azido-3-O-benzyl-6-deoxy-1,2-O-(1-methylethylidene)-α-D-glucofuranose

: 477329-89-8
2,4-di-O-acetyl-6-azido-3-O-benzyl-6-deoxy-α-L-idopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 5 steps

1.1: (COCl)2; DMSO; DIPEA / CH₂Cl₂ / -78 - 0 °C

2.1: 2.57 g / NaBH₄ / methanol / 0 °C

3.1: AcOH; H₂O; TFA / 2 h / 60 °C

3.2: 43 percent / TFA / 20 °C

4.1: hydrazine acetate / dimethylformamide / 20 °C

5.1: DBU / CH₂Cl₂ / 20 °C

With sodium tetrahydroborate; oxalyl dichloride; water; hydrazinium monoacetate; acetic acid; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Swern oxidation;
DOI:10.1021/ol026588r