2,3,4-tri-O-benzyl-6-O-[4-(tert-butoxycarbonyl)benzyl]-α-D-glucopyranosyl trichloroacetimidate

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Chemical Name:2,3,4-tri-O-benzyl-6-O-[4-(tert-butoxycarbonyl)benzyl]-α-D-glucopyranosyl trichloroacetimidate
CAS No.:273935-10-7
Molecular Formula:C₄₁H₄₄Cl₃NO₈
Molecular Weight:785.161
Hs Code.:

Synonyms:2,3,4-tri-O-benzyl-6-O-[4-(tert-butoxycarbonyl)benzyl]-α-D-glucopyranosyl trichloroacetimidate

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Chemical Property of 2,3,4-tri-O-benzyl-6-O-[4-(tert-butoxycarbonyl)benzyl]-α-D-glucopyranosyl trichloroacetimidate

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Technology Process of 2,3,4-tri-O-benzyl-6-O-[4-(tert-butoxycarbonyl)benzyl]-α-D-glucopyranosyl trichloroacetimidate

There total 4 articles about 2,3,4-tri-O-benzyl-6-O-[4-(tert-butoxycarbonyl)benzyl]-α-D-glucopyranosyl 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: 82.0%

: 545-06-2
trichloroacetonitrile

: 2,3,4-tri-O-benzyl-6-O-[4-(tert-butoxycarbonyl)benzyl]-D-glucopyranose

: 273935-10-7
2,3,4-tri-O-benzyl-6-O-[4-(tert-butoxycarbonyl)benzyl]-α-D-glucopyranosyl trichloroacetimidate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; for 4h;
DOI:10.1016/S0008-6215(99)00327-4

Reference yield:

: 78184-40-4
1-O-allyl-2,3,4-tri-O-benzyl-α-D-glucopyranoside

: 273935-10-7
2,3,4-tri-O-benzyl-6-O-[4-(tert-butoxycarbonyl)benzyl]-α-D-glucopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 86 percent / NaH / dimethylformamide / 12 h / 85 °C

2.1: DABCO / RhCl(PPh₃)3 / aq. ethanol / 6 h / Heating

2.2: 81 percent / I₂; H₂O / pyridine / 0.17 h / 20 °C

3.1: 82 percent / DBU / CH₂Cl₂ / 4 h

With 1,4-diaza-bicyclo[2.2.2]octane; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; RhCl(PPh₃)3; In ethanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Substitution / 2.1: Isomerization / 2.2: Hydrolysis / 3.1: Addition;
DOI:10.1016/S0008-6215(99)00327-4

Reference yield:

: 108052-76-2
4-(bromomethyl)benzoic acid 1,1-dimethylethyl ester

: 273935-10-7
2,3,4-tri-O-benzyl-6-O-[4-(tert-butoxycarbonyl)benzyl]-α-D-glucopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 86 percent / NaH / dimethylformamide / 12 h / 85 °C

2.1: DABCO / RhCl(PPh₃)3 / aq. ethanol / 6 h / Heating

2.2: 81 percent / I₂; H₂O / pyridine / 0.17 h / 20 °C

3.1: 82 percent / DBU / CH₂Cl₂ / 4 h

With 1,4-diaza-bicyclo[2.2.2]octane; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; RhCl(PPh₃)3; In ethanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Substitution / 2.1: Isomerization / 2.2: Hydrolysis / 3.1: Addition;
DOI:10.1016/S0008-6215(99)00327-4