2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-6-O-(p-methoxyphenyl)-α-L-idopyranosyl trichloroacetimidate

Base Information

Chemical Name:2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-6-O-(p-methoxyphenyl)-α-L-idopyranosyl trichloroacetimidate
CAS No.:1447801-73-1
Molecular Formula:C₃₄H₃₄Cl₃NO₁₀
Molecular Weight:723.004
Hs Code.:

Synonyms:

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Chemical Property of 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-6-O-(p-methoxyphenyl)-α-L-idopyranosyl trichloroacetimidate

Chemical Property:

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Technology Process of 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-6-O-(p-methoxyphenyl)-α-L-idopyranosyl trichloroacetimidate

There total 4 articles about 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-6-O-(p-methoxyphenyl)-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:

: 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-6-O-(p-methoxyphenyl)-α/β-L-idopyranose

: 545-06-2
trichloroacetonitrile

: 1447801-73-1
2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-6-O-(p-methoxyphenyl)-α-L-idopyranosyl trichloroacetimidate

: 1447801-74-2
2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-6-O-(p-methoxyphenyl)-β-L-idopyranosyl trichloroacetimidate

Guidance literature:: 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-6-O-(p-methoxyphenyl)-α/β-L-idopyranose; trichloroacetonitrile; In dichloromethane; for 0.5h; Molecular sieve;

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 2h; Overall yield = 56 %; Overall yield = 1.27 g;
DOI:10.1021/jo400467g

Reference yield:

: C₂₁H₂₂O₆

: 1447801-73-1
2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-6-O-(p-methoxyphenyl)-α-L-idopyranosyl trichloroacetimidate

: 1447801-74-2
2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-6-O-(p-methoxyphenyl)-β-L-idopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 5 steps

1.1: zinc(II) iodide / dichloromethane / 20 °C

2.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 20 °C

3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 5 h / 20 °C

4.1: N-iodo-succinimide; trifluorormethanesulfonic acid / tetrahydrofuran / 6 h / 20 °C

5.1: dichloromethane / 0.5 h / Molecular sieve

5.2: 2 h / 0 °C

With dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; di-isopropyl azodicarboxylate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; zinc(II) iodide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo400467g

Reference yield:

: 175978-41-3
phenyl 2-O-benzoyl-3-O-benzyl-4,6-dihydroxylthio-α-L-idopyranoside

: 1447801-73-1
2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-6-O-(p-methoxyphenyl)-α-L-idopyranosyl trichloroacetimidate

: 1447801-74-2
2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-6-O-(p-methoxyphenyl)-β-L-idopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 4 steps

1.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 20 °C

2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 5 h / 20 °C

3.1: N-iodo-succinimide; trifluorormethanesulfonic acid / tetrahydrofuran / 6 h / 20 °C

4.1: dichloromethane / 0.5 h / Molecular sieve

4.2: 2 h / 0 °C

With dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; di-isopropyl azodicarboxylate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo400467g