(2S,3S,4S,5R,6S)-3,4,5-Tris-allyloxycarbonyloxy-6-[4-(4-nitro-phenoxycarbonyloxymethyl)-phenylcarbamoyloxy]-tetrahydro-pyran-2-carboxylic acid allyl ester

Base Information

Chemical Name:(2S,3S,4S,5R,6S)-3,4,5-Tris-allyloxycarbonyloxy-6-[4-(4-nitro-phenoxycarbonyloxymethyl)-phenylcarbamoyloxy]-tetrahydro-pyran-2-carboxylic acid allyl ester
CAS No.:922173-31-7
Molecular Formula:C₃₆H₃₆N₂O₁₉
Molecular Weight:800.684
Hs Code.:

(2S,3S,4S,5R,6S)-3,4,5-Tris-allyloxycarbonyloxy-6-[4-(4-nitro-phenoxycarbonyloxymethyl)-phenylcarbamoyloxy]-tetrahydro-pyran-2-carboxylic acid allyl ester

Synonyms:(2S,3S,4S,5R,6S)-3,4,5-Tris-allyloxycarbonyloxy-6-[4-(4-nitro-phenoxycarbonyloxymethyl)-phenylcarbamoyloxy]-tetrahydro-pyran-2-carboxylic acid allyl ester

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Chemical Property of (2S,3S,4S,5R,6S)-3,4,5-Tris-allyloxycarbonyloxy-6-[4-(4-nitro-phenoxycarbonyloxymethyl)-phenylcarbamoyloxy]-tetrahydro-pyran-2-carboxylic acid allyl ester

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Technology Process of (2S,3S,4S,5R,6S)-3,4,5-Tris-allyloxycarbonyloxy-6-[4-(4-nitro-phenoxycarbonyloxymethyl)-phenylcarbamoyloxy]-tetrahydro-pyran-2-carboxylic acid allyl ester

There total 8 articles about (2S,3S,4S,5R,6S)-3,4,5-Tris-allyloxycarbonyloxy-6-[4-(4-nitro-phenoxycarbonyloxymethyl)-phenylcarbamoyloxy]-tetrahydro-pyran-2-carboxylic acid allyl 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: 91.0%

: 922173-27-1
(2S,3S,4S,5R,6S)-3,4,5-Tris-allyloxycarbonyloxy-6-(4-hydroxymethyl-phenylcarbamoyloxy)-tetrahydro-pyran-2-carboxylic acid allyl ester

: 7693-46-1
4-Nitrophenyl chloroformate

: 922173-31-7
(2S,3S,4S,5R,6S)-3,4,5-Tris-allyloxycarbonyloxy-6-[4-(4-nitro-phenoxycarbonyloxymethyl)-phenylcarbamoyloxy]-tetrahydro-pyran-2-carboxylic acid allyl ester

Guidance literature:: With pyridine; In dichloromethane; at 0 ℃; for 2h;
DOI:10.1021/jo0612675

Reference yield:

: 619-73-8
4-nitrobenzyl chloride

: 922173-31-7
(2S,3S,4S,5R,6S)-3,4,5-Tris-allyloxycarbonyloxy-6-[4-(4-nitro-phenoxycarbonyloxymethyl)-phenylcarbamoyloxy]-tetrahydro-pyran-2-carboxylic acid allyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 98 percent / imidazole / dimethylformamide / 2 h / 20 °C

2: 84 percent / ammonium formate / Pd/C / ethanol / 5 h / 20 °C

3: 86 percent / triethylamine / toluene / 3 h / 70 °C

4: 69 percent / triethylamine / toluene / 1.5 h / 0 °C

5: 81 percent / acetic acid; TBAF / tetrahydrofuran / 20 h / 20 °C

6: 91 percent / pyridine / CH₂Cl₂ / 2 h / 0 °C

With pyridine; 1H-imidazole; tetrabutyl ammonium fluoride; ammonium formate; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo0612675

Reference yield:

: 135605-97-9
tert-butyldimethyl-4-nitrobenzyloxysilane

: 922173-31-7
(2S,3S,4S,5R,6S)-3,4,5-Tris-allyloxycarbonyloxy-6-[4-(4-nitro-phenoxycarbonyloxymethyl)-phenylcarbamoyloxy]-tetrahydro-pyran-2-carboxylic acid allyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 84 percent / ammonium formate / Pd/C / ethanol / 5 h / 20 °C

2: 86 percent / triethylamine / toluene / 3 h / 70 °C

3: 69 percent / triethylamine / toluene / 1.5 h / 0 °C

4: 81 percent / acetic acid; TBAF / tetrahydrofuran / 20 h / 20 °C

5: 91 percent / pyridine / CH₂Cl₂ / 2 h / 0 °C

With pyridine; tetrabutyl ammonium fluoride; ammonium formate; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; toluene;
DOI:10.1021/jo0612675