O-(3,4,6-tri-O-acetyl-2-tert-butoxycarbonamido-2-deoxy-D-glucopyranosylidene)amino N-phenylcarbamate

Base Information

Chemical Name:O-(3,4,6-tri-O-acetyl-2-tert-butoxycarbonamido-2-deoxy-D-glucopyranosylidene)amino N-phenylcarbamate
CAS No.:883865-67-6
Molecular Formula:C₂₄H₃₁N₃O₁₁
Molecular Weight:537.524
Hs Code.:

Synonyms:O-(3,4,6-tri-O-acetyl-2-tert-butoxycarbonamido-2-deoxy-D-glucopyranosylidene)amino N-phenylcarbamate

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Chemical Property of O-(3,4,6-tri-O-acetyl-2-tert-butoxycarbonamido-2-deoxy-D-glucopyranosylidene)amino N-phenylcarbamate

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Technology Process of O-(3,4,6-tri-O-acetyl-2-tert-butoxycarbonamido-2-deoxy-D-glucopyranosylidene)amino N-phenylcarbamate

There total 6 articles about O-(3,4,6-tri-O-acetyl-2-tert-butoxycarbonamido-2-deoxy-D-glucopyranosylidene)amino N-phenylcarbamate 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: 71.0%

: 883865-66-5
3,4,6-tri-O-acetyl-2-tert-butoxycarbonamido-2-deoxy-D-gluconohydroximo-1,5-lactone

: 103-71-9
phenyl isocyanate

: 883865-67-6
O-(3,4,6-tri-O-acetyl-2-tert-butoxycarbonamido-2-deoxy-D-glucopyranosylidene)amino N-phenylcarbamate

Guidance literature:: With triethylamine; In tetrahydrofuran; at 20 ℃; for 3h;
DOI:10.1039/b516273d

Reference yield:

: acetic acid 3-acetoxy-2-acetoxymethyl-5-tert-butoxycarbonylamino-6-hydroxy-tetrahydro-pyran-4-yl ester

: 883865-67-6
O-(3,4,6-tri-O-acetyl-2-tert-butoxycarbonamido-2-deoxy-D-glucopyranosylidene)amino N-phenylcarbamate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 9.5 g / H₂NOH*HCl; pyridine / methanol / 2 h / Heating

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 0.08 h / -45 °C

2.2: N-chlorosuccinimide / CH₂Cl₂ / 2.5 h / -40 - 20 °C

3.1: 71 percent / Et₃N / tetrahydrofuran / 3 h / 20 °C

With pyridine; hydroxylamine hydrochloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1039/b516273d

Reference yield:

: 883865-65-4
3,4,6-tri-O-acetyl-2-tert-butoxycarbonamido-2-deoxy-D-glucose oxime

: 883865-67-6
O-(3,4,6-tri-O-acetyl-2-tert-butoxycarbonamido-2-deoxy-D-glucopyranosylidene)amino N-phenylcarbamate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 0.08 h / -45 °C

1.2: N-chlorosuccinimide / CH₂Cl₂ / 2.5 h / -40 - 20 °C

2.1: 71 percent / Et₃N / tetrahydrofuran / 3 h / 20 °C

With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1039/b516273d