(2S,3S,4S,5R,6S)-6-[4-Chloro-2-(6-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-phenoxy]-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

Chemical Name:(2S,3S,4S,5R,6S)-6-[4-Chloro-2-(6-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-phenoxy]-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester
CAS No.:192203-23-9
Molecular Formula:C₂₁H₁₈Cl₂N₂O₈
Molecular Weight:497.289
Hs Code.:

(2S,3S,4S,5R,6S)-6-[4-Chloro-2-(6-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-phenoxy]-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

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Chemical Property of (2S,3S,4S,5R,6S)-6-[4-Chloro-2-(6-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-phenoxy]-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

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Technology Process of (2S,3S,4S,5R,6S)-6-[4-Chloro-2-(6-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-phenoxy]-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 5 articles about (2S,3S,4S,5R,6S)-6-[4-Chloro-2-(6-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-phenoxy]-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester 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:

: 4743-17-3
5-Chloroisatoic anhydride

: 192203-23-9
(2S,3S,4S,5R,6S)-6-[4-Chloro-2-(6-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-phenoxy]-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 81 percent / NH₃ gas / tetrahydrofuran / Ambient temperature

2: 1.) p-TsOH, 2.) DDQ / 1.) MeOH, room temperature, 2 h; reflux, 1 h, 2.) 0 deg C, 2 h

With ammonia; toluene-4-sulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran;
DOI:10.1016/S0040-4020(97)00413-4

Reference yield:

: 635-93-8
5-chlorosalicyclaldehyde

: 192203-23-9
(2S,3S,4S,5R,6S)-6-[4-Chloro-2-(6-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-phenoxy]-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 86 percent / Ag₂CO₃, 2,4,6-collidine / CH₂Cl₂ / 96 h / Ambient temperature

2: 94 percent / NaOMe / methanol / 1.) 0 deg C, 2 h, 2.) room temperature, 4 h

3: 1.) p-TsOH, 2.) DDQ / 1.) MeOH, room temperature, 2 h; reflux, 1 h, 2.) 0 deg C, 2 h

With 2,4,6-trimethyl-pyridine; sodium methylate; toluene-4-sulfonic acid; silver carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane;
DOI:10.1016/S0040-4020(97)00413-4

Reference yield:

: 148580-09-0
(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-(4-chloro-2-formyl-phenoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester

: 192203-23-9
(2S,3S,4S,5R,6S)-6-[4-Chloro-2-(6-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-phenoxy]-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 94 percent / NaOMe / methanol / 1.) 0 deg C, 2 h, 2.) room temperature, 4 h

2: 1.) p-TsOH, 2.) DDQ / 1.) MeOH, room temperature, 2 h; reflux, 1 h, 2.) 0 deg C, 2 h

With sodium methylate; toluene-4-sulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol;
DOI:10.1016/S0040-4020(97)00413-4