allyl 2-O-benzyl-3-deoxy-4,3-(2-trichloromethyl-1-oxa-3-azaprop-2-eno)-α-D-fucopyranoside

Base Information

Chemical Name:allyl 2-O-benzyl-3-deoxy-4,3-(2-trichloromethyl-1-oxa-3-azaprop-2-eno)-α-D-fucopyranoside
CAS No.:720694-46-2
Molecular Formula:C₁₈H₂₀Cl₃NO₄
Molecular Weight:420.72
Hs Code.:

Synonyms:allyl 2-O-benzyl-3-deoxy-4,3-(2-trichloromethyl-1-oxa-3-azaprop-2-eno)-α-D-fucopyranoside

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Chemical Property of allyl 2-O-benzyl-3-deoxy-4,3-(2-trichloromethyl-1-oxa-3-azaprop-2-eno)-α-D-fucopyranoside

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Technology Process of allyl 2-O-benzyl-3-deoxy-4,3-(2-trichloromethyl-1-oxa-3-azaprop-2-eno)-α-D-fucopyranoside

There total 4 articles about allyl 2-O-benzyl-3-deoxy-4,3-(2-trichloromethyl-1-oxa-3-azaprop-2-eno)-α-D-fucopyranoside 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: 68.0%

: 100-39-0
benzyl bromide

: 720694-44-0
(3aR,4R,6S,7R,7aR)-6-Allyloxy-4-methyl-2-trichloromethyl-3a,6,7,7a-tetrahydro-4H-pyrano[4,3-d]oxazol-7-ol

: 720694-46-2
allyl 2-O-benzyl-3-deoxy-4,3-(2-trichloromethyl-1-oxa-3-azaprop-2-eno)-α-D-fucopyranoside

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 90h;
DOI:10.1016/j.tet.2005.04.013

Reference yield:

: 201858-29-9
allyl α-D-isopropylidene-α-D-fucopyranoside

: 720694-46-2
allyl 2-O-benzyl-3-deoxy-4,3-(2-trichloromethyl-1-oxa-3-azaprop-2-eno)-α-D-fucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: CSA / dimethylformamide / 40 °C

1.2: pyridine; dimethylformamide / 20 °C

1.3: 58 percent / AcOH / pyridine; dimethylformamide / 20 °C

2.1: CSA / CH₂Cl₂; pyridine / 0.67 h / 0 °C

3.1: NaOMe / methanol; CH₂Cl₂ / 2 h / 20 °C

4.1: DBU / CH₂Cl₂ / 1 h / 0 °C

5.1: 965 mg / silica gel (0.063-0.200 mm) / CHCl₃ / 0.17 h / 45 °C

6.1: 68 percent / NaH / dimethylformamide / 20 °C

With camphor-10-sulfonic acid; sodium methylate; silica gel; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In pyridine; methanol; dichloromethane; chloroform; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2004.04.065

Reference yield:

: 1021496-24-1
2,2,2-Trichloro-acetimidic acid (1R,2S,4R,5S,6R)-2-allyloxy-4-methyl-3,7-dioxa-bicyclo[4.1.0]hept-5-yl ester

: 720694-46-2
allyl 2-O-benzyl-3-deoxy-4,3-(2-trichloromethyl-1-oxa-3-azaprop-2-eno)-α-D-fucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 965 mg / silica gel (0.063-0.200 mm) / CHCl₃ / 0.17 h / 45 °C

2: 68 percent / NaH / dimethylformamide / 20 °C

With silica gel; sodium hydride; In chloroform; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2004.04.065